Pervious Year Question (PYQ) - 2022

CONTENT
S.No Pages
1. Nomenclature of organic compounds 04 – 11
2. Isomerism 12 – 21
3. General Organic Chemistry 22 – 37
4. Hydrocarbon 38 – 61
5. Halogen Derivative 62 – 88
6. Aromatic Compound 89 – 121
7. Alcohols & Ethers 122 – 135
8. Grignard Reagent 136 – 144
9. Carbonyl Compound 145 – 168
10. Carboxylic Acid and its derivative 169 – 185
11. Biomolecule & Polymer 186 – 214

Nomenclature | JEE Main
1. Of the following compounds which has a wrong IUPAC name - [AIEEE-2002]

 CH3 – CH2 – CH2 – C – O – CH2 – CH3
||
O
ethyl butanoate
 CH3 – CH – C – CH – CH3
| || |
CH3 O CH3
2,4- dimethyl -3- pentanone
CH3
|
 H3C – CH – CH – CH3
|
OH
2-methyl -3- butanol
IV CH3 – CH2 – CH2 – CHO
butanal
(A)  (B)  (C)  (D) IV
2. The IUPAC name of CH3COCH(CH3)2 is – [AIEEE-2003]

(A) 4-methylisopropyl ketone (B) 3-methyl-2-butanone
(C) Isopropylmethyl ketone (D) 2-methyl-3-butanone
3. The IUPAC name of the compound [AIEEE-2004]
is -
(A) 3,3 -dimethyl-1-hydroxy cyclohexane (B) 1, 1 – dimethyl–3– hydroxy cyclohexane

(C) 3,3-dimethyl-1-cyclohexanol (D) 1,1 - dimethyl - 3- cyclohexanol
4. The IUPAC name of the compound shown below is - [AIEEE-2006]
(A) 6-bromo-2-chlorocyclohexene (B) 3-bromo-1-chlorocyclohexene

(C) 1-bromo-3-chlorocylohexene (D) 2-bromo-6-chlorocycohex-1-ene
5. The IUPAC name of [AIEEE-2007]
is –
(A) 1, 1-diethyl-2-dimethylpentane (B) 4, 4-dimethyl-5, 5-diethylpentane

(C) 5, 5-diethyl-4, 4-dimethylpentane (D) 3-ethyl-4, 4 dimethylheptane
6. The correct decreasing order of priority for the functional groups of organic compounds in the IUPAC
system of nomenclature is [AIEEE 2008]
(A) –SO3H, –COOH, –CONH2, –CHO
(B) –CHO, –COOH, –SO3H, –CONH2
(C) –CONH2, –CHO, –SO3H, –COOH
(D) –COOH, –SO3H, –CONH2, –CHO
7. The IUPAC name of neopentane is : [AIEEE -2009]

(A) 2-methylpropane (B) 2, 2-dimethylbutane
(C) 2-methylbutane (D) 2, 2-dimethylpropane
8. The IUPAC name of compound is :- [AIEEE -2012 (Online)]
(A) 1, 2-Epoxy propane (B) Propylene oxide

(C) 1, 2-Oxo propane (D) 1, 2-Propoxide
9. The IUPAC name of the followig compounds is : [AIEEE -2012 (Online)]
(A) (Z) – 5– hepten – 3 – yne (B) (Z) – 2– hepten – 4 – yne

(C) (E) – 5– hepten – 3 – yne (D) (E) – 2– hepten – 4 – yne
10. Aspirin is known as : [AIEEE -2012]

(A) Acetyl salicyclic acid (B) Phenyl salicylate
(C) Acetyl salicylate (D) Methyl salicylic acid
11. The IUPAC name for the following compound is [JEE Main 2019]
CH3
H3C CH
CH3
CH2
(A) 3-methyl-4-(3-methylprop-1-enyl)-1-heptyne
(B) 3, 5-dimethyl-4-propylhept-6-en-1-yne
(C) 3-methyl-4-(1-methylprop-2-ynyl)-1-heptene
(D) 3, 5-dimethyl-4-propylhept1-en-6-yne
12. The correct IUPAC name of the following compound is [JEE Main 2019]
(A) 2-methyl-5-nitro-1-chlorobenzene
NO2
(B) 3-chloro-1-methyl-nitrobenzene
Cl
CH3
(C) 2-chloro-1-methyl 1-4-nitribenzene

(D) 5-chloro-4-methyl 1-1-nitrobenzene
13. Which of the following compounds will show the maximum ‘enol’ content ? [JEE Main 2019]
(A) CH3COCH3 (B) CH3COCH2COCH3
(C) CH3COCH2COOC2H5 (D) CH3COCH2CONH2
14. The IUPAC name of the following compound is [JEE Main 2019]
CH3 OH
H3C CH CH CH2 COOH
(A) 4,4-dimethyl-3-hydroxybutanoic acid
(B) 2-methyl-3-hydroxypentan-5-oic acid
(C) 3-hydroxy-4-methylpentanoic acid
(D) 4-methyl-3-hydroxypentanoic acid
15. What is the IUPAC name of the following compound ? [JEE Main 2019]
CH3 CH3
H
H
Br
CH3
(A) 3-bromo-3-methyl-1, 2-dimethylprop-1-ene
(B) 3-bromo-1, 2-dimethylbut-1-ene
(C) 2-bromo-3-methylpent-3-ene
(D) 4-bromo-methylpent-2-ene
16. The IUPAC name for the following compound is : [JEE-Main-2020]
(A) 2,5-dimethyl-6-carboxy-hex-3-enal
(B) 2,5-dimethyl-5-carboxy-hex-3-enal
(C) 6-formyl-2-methyl-hex-3-enoic
(D) 2,5-dimethyl-6-oxo-hex-3-enoic acid
17. The IUPAC name of the following compound is : [JEE-Main-2020]
(A) 3-bromo-5-methylcyclopentane
(B) 3-bromo-5-methylcyclopentanoic acid
(C) 5-bromo-5-methylcyclopentanoic acid
(D) 4-bromo-2-methylcyclopentanecarboxylic acid
18. The IUPAC name of the following compound is : [JEE-Main-2020]
(1) 2-nitro-4-hydroxymethyl-5 amino benzaldehyde

(2) 3-amino-4-hydroxymethyl-5-nitrogenbenzaldehyde
(3) 4-amino-2-formyl-5-hydroxymethyl nitrogenbenzene
(4) 5-amino-4-hydroxymethyl-2-nitrobenzaldehyde
1 2 3 4
19. In CH2 = C = CH–CH3 molecule, the hybridization of carbon 1, 2, 3 and 4 respectively are:
[JEE-Mains (26-Feb_Shift -2)2021]

(A) sp2, sp, sp2, sp3 (B) sp2, sp2, sp2, sp3
(C) sp2, sp3, sp2, sp3 (D) sp3, sp, sp3, sp3
20. Mesityl oxide is a common name of : [JEE-Mains (17-March_Shift -1)2021]

(A) 3-Methyl cyclohexane carbaldehyde (B) 4-Methyl pent-3-en-2-one
(C) 2,4-Dimethyl pentan-3-one (D) 2-Methyl cyclohexanone
21. The number of sigma bonds in [JEE-Mains (25-July_Shift -1)2021]
H3C C = CH C C H is ____________ .
22. The IUPAC name of ethylidene chloride is : [JEE-Mains (25-Jun-Shift-1)2022]

(A) 1-Chloroethene (B) 1-Chloroethyne
(C) 1,2-Dichloroethane (D) 1,1-Dichloroethane
23. The correct IUPAC name of the following compound is : [JEE-Mains (28-Jun-Shift-2)2022]
H
O 2N
O O
(A) 4-methyl-2-nitro-5-oxohept-3-enal (B) 4-methyl-5-oxo-2-nitrohept-3-enal
(C) 4-methyl-6-nitro-3-oxohept-4-enal (D) 6-formyl-4-methyl-2-nitrohex-3-enal
24. The number of sp3 hybridised carbons in an acyclic neutral compound with molecular formula
C4H5N is __________. [JEE-Mains (25-July_Shift-1)2022]
25. The correct decreasing order of priority of functional groups in naming an organic compound as
per IUPAC system of nomenclature is [JEE-Mains (26-July_Shift-2)2022]
(A) –COOH > –CONH2 > –COCl > – CHO (B) –SO3H > –COCl > –CONH2 > –CN
(C) –COOR > –COCl > –NH2 > C O (D) –COOH > –COOR > –CONH2 > –COCl
[JEE-ADVANCED]
1. The IUPAC name of the compound having the formula is : [JEE 1984]
CH 3
|
H 3C  C  CH  CH 2
|
CH 3
(A) 3,3,3-trimethyl-1-propene (B) 1,1,1-trimethyl-2-propene

(C) 3,3-dimethyl-1-butene (D) 2,2-dimethyl-3-butene
2. Write the IUPAC name of CH3CH2CH = CHCOOH [JEE 1986]
3. The IUPAC name of the compound CH2=CH–CH(CH3)2 is : [JEE 1987]

(A) 1,1-dimethyl-2-propene (B) 3-methyl-1-butene
(C) 2-vinyl propane (D) None of the above
4. The number of sigma and pi-bonds in 1-butene 3-yne are: [JEE 1989]
(A) 5 sigma and 5 pi (B) 7 sigma and 3 pi
(C) 8 sigma and 2 pi (D) 6 sigma and 4 pi
5. Write I.U.P.A.C name of following : [JEE 1990]
(a) Me = methyl group
CH 3
|
(b) H 3C  N — CH  CH 2CH 3
| |
CH 3 C 2 H 5
6. Write IUPAC name of succinic acid. [JEE 1994]
7. The IUPAC name of C6H5COCl is [JEE 2006]

(A) Benzoyl chloride (B) Benzene chloro ketone
(C) Benzene carbonyl chloride (D) Chloro phenyl ketone
8. The IUPAC name of the following compound is [JEE 2009]

CN
Br
HO
(A) 4-Bromo-3-cyanophenol
(B) 2-Bromo-5-hydroxybenzonitrile
(C) 2-Cyano-4-hydroxybromobenzene
(D) 6-Bromo-3-hydroxybenzonitrile
9. The correct structure of ethylenediaminetetraacetic acid (EDTA) is [IIT-JEE 2010]
HOOC–CH 2
CH2–COOH
(A) N–CH=CH–N
HOOC–CH 2 CH2–COOH
HOOC COOH
(B) N–CH2–CH2–N
HOOC COOH
HOOC–CH 2
CH2–COOH
(C) N–CH2–CH 2–N
HOOC–CH 2 CH2–COOH
COOH
HOOC–CH2 CH2
H
N– CH – CH – N
(D) H CH2 CH2–COOH
HOOC
10. The total number of lone-pairs of electrons in melamine is [JEE Advance 2013]
11. The correct combination of names for isomeric alcohols with molecular formula C4H10O is/are
(A) tert-butanol and 2-methylpropan-2-ol
(B) tert-butanol and 1,1-dimethylethan-1-ol
(C) n-butanol and butan-1-ol
(D) isobutyl alcohol and 2-methylpropan-1-ol [JEE Advance 2014]
12. The IUPAC name(s) of the following compound is(are) [JEE Advance 2017]
H3C Cl
(A) 1-chloro-4-methylbenzene (B) 4-chlorotoluene

(C) 1-methyl-4-chlorobenzene (D) 4-methylchlorobenzene
13. Which one of the following structures has the IUPAC name 3-ethynyl-2-hydroxy-4-methylhex-3-en-5-
ynoic acid ? [JEE Advance 2020]
(A) (B) (C) (D)

Previous Year | JEE Main
1. C 2. B 3. C 4. B 5. D 6. D 7. D
8. A 9. D 10. A 11. D 12. C 13. B 14. C
15. D 16. D 17. D 18. D 19. A 20. B 21. 10
22. D 23. C 24. 0 or 1 25. B
Previous Year | JEE Advanced
1. C
CH3  CH 2  CH  CH  COOH
2. 5 4 3 2 1
Pent-2-en-1-oic acid or Pent-2-enoic acid
3. B 4. B
5. (a) 5,6 diethyl 3 methyl dec 4 ene (b) N,N, 3 trimethyl 3 pentanamine
6. Butane 1,4 dioic acid 7. C 8. B 9. C 10. 6
11. ACD 12. AB 13. D

Isomerism | JEE Main
1. Which types of isomerism is shown by 2,3–dichlorobutane ? [AIEEE-2005]

(A) Optical (B) Diastereo (C) Structural (D) Geometric
2. Increasing order of stability among the three main conformations (i.e. Eclipse, Anti, Gauche) of
2-fluoroethanol is [AIEEE 2006]
(A) Gauche, Eclipse, Anti (B) Eclipse, Anti, Gauche
(C) Anti, Gauche, Eclipse (D) Eclipse, Gauche, Anti
3. Which of the following molecules is expected to rotate the plane of plane-polarised light ? [AIEEE-2007]
COOH
H2N H
(A) (B) (C) (D)
H
4. Which one of the following conformations of cyclohexane is chiral ? [AIEEE-2007]

(A) Twist boat (B) Rigid (C) Chair (D) Boat
5. The absolute configuration of
HO2C CO2H
is [AIEEE-2008]
OH
HO H H
(A) R, R (B) R, S (C) S, R (D) S, S
6. The alkene that exhibits geometrical isomerism is : [AIEEE-2009]

(A) propene (B) 2-methyl propene (C) 2-butene (D) 2- methyl -2- butene
7. The number of stereoisomers possible for a compound of the molecular formula [AIEEE-2009]
CH3–CH=CH–CH(OH) –Me is :
(A) 3 (B) 2 (C) 4 (D) 6
8. Out of the following, the alkene that exhibits optical isomerism is [AIEEE-2010]
(A) 3–methyl–2–pentene (B) 4–methyl–1–pentene
(C) 3–methyl–1–pentene (D) 2–methyl–2–pentene
9. Identify the compound that exhibits tautomerism [AIEEE-2011]

(A) 2 - butene (B) lactic acid (C) 2 - pentanone (D) phenol
10. How many chiral compounds are possible on monochlorination of 2–methyl butane? [JEE Main 2012]
(A) 4 (B) 6 (C) 8 (D) 2
11. Which of the following compounds will exhibit geometrical isomerism ? [JEE Main 2015]
(A) 1-Phenyl-2-butene (B) 3-Phenyl -1-butene
(C) 2-Phenyl-1-butene (D) 1, 1-Diphenyl-1-propane
12. The absolute configuration of [JEE Main 2016]
CO2H
H OH
H Cl is:
CH3
(A) (2S, 3R) (B) (2S, 3S) (C) (2R, 3R) (D) (2R, 3S)
13. In the following structure, the double bonds are marked as I, II, III and IV
II [JEE Mains Online-2017]
III
I IV
(A) III (B) I (C) and I III (D) and V

III I
14. The total number of optically active compounds formed inthet following reaction is :
[JEE Mains Online, 2018]
O
HBr
(A) Two (B) Four (C) Six (D) Zero
15. The number of chiral carbons present in the molecule given below is ..........
16. The number of chiral centres present in threonine is ............... [JEE Mains Online, 2020]
17. Among the following compounds, geometrical isomerism is exhibited by :

CHCl CHCl CHCl CH2
(A) (B) (C) (D)

CH3 H3C CH3
CI
18. Which of the follwing compounds shows geometrical isomerism ? JEE Mains Online, 2020]
(A) 4-methylpent-1-ene (B) 2-methylpent-2-ene
(C) 4-methylpent-2-ene (D) 2-methylpent-1-ene
19. Compound with molecular formula C3H6O can show : [JEE-Mains (18-March_Shift -1)2021]
(A) Both positional isomerism and metamerism (B) Metamerism
(C) Positional isomerism (D) Functional group isomerism
20. Which one of the following pairs of isomers is an example of metamerism ?
(A) CH3CH2CH2CH2CH3 and [JEE-Mains (20-July_Shift-2)2021]
(B)
(C)
(D)
21. Which one of the following molecules does not show stereo isomerism ?
[JEE-Mains (22-July_Shift-2)2021]
(A) 3, 4-dimethylhex-3-ene (B) 4-Methylhex-1-ene
(C) 3-Methylhex-1-ene (D) 3-Ethylhex-3-ene
22. The number of acyclic structural isomers (including geometrical isomers) for pentene are _____.
23. Staggered and eclipsed conformers of ethane are: [JEE-Mains (27-July_Shift-1)2021]

(A) Enantiomers (B) Rotamers
(C) Mirror images (D) Polymers
24. The dihedral angle in staggered form of Newman projection of 1,1,1-Trichloro ethane is______ degree.
(Round off to the nearest integer) [JEE-Mains (27-July_Shift-2)2021]
25. The number of stereoisomers possible for 1,2-dimethyl cyclopropane is :

[JEE-Mains (26-August_Shift-2)2021]
(A) One (B) Four (C) Two (D) Three
26. Choose the correct name for compound given below :
Br
(A) (4E)–5–Bromo-hex–4–en–2–yne (B) (2E)–2–Bromo-hex–4–en–2–yne

(C) (4E)–5–Bromo-hex–2–en–2–yne (D) (2E)–2–Bromo-hex–2–en–4–yne
27. Arrange the following conformational isomers of n-butane in order of their increasing potential energy:
CH3 CH3 CH3 H
CH3 CH 3 H
H H H
H
H H H H H H H
CH 3 CH 3
CH 3 H H H
I II III IV
(A) II < III < IV < I (B) I < III < IV < II (C) I < IV < III < II (D) II < IV < III < I
28. In the following structures, which one is having staggered conformation with maximum dihedral angle
? [JEE-Mains (25-Jun-Shift-1)2022]
CH3
CH3 CH3 CH3 CH
H H 3
H CH3 H CH3
(A) (B) H (C) (D) H

H H
H CH3H H H
H H CH3 H
29. Which will have the highest enol content? [JEE-Mains (26-Jun-Shift-1)2022]
O O O O
O
(A) (B) (C) (D)

O O O
30. Total number of possible stereoisomers of dimethyl cyclopentane is

[JEE-Mains (27-Jun-Shift-1)2022]
31. Observe structures of the following compounds

NH2
Cl OH
H 2N OH
O OH
O
The total number of structures/compounds which possess asymmetric carbon atoms ________is
32. The mixture of chloroxylenol and terpineol is an example of [JEE-Mains (29-Jun-Shift-2)2022]

(A) antiseptic (B)pesticide (C) disinfectant (D) narcotic analgesic
33. Optical activity of an enantiomeric mixture is +12.6° and the specific rotation of (+) isomer is +30°. The
optical purity is ________%. [JEE-Mains (27-July_Shift-1)2022]
34. Given below are two statement [JEE-Mains (29-July_Shift-2)2022]
CH3
NO2
H
Statement I : The compound is optically active
(A)
CH3
CH3
O 2N
Statement II : H
is mirror image of above compound A.
CH3
In the light of the above statement, choose the most appropriate answer from the options given below
(A) Both Statement I and Statement II are correct.
(B) Both Statement I and Statement II are incorrect.
(C) Statement I is correct but Statement II is incorrect.
(D) Statement I is incorrect but Statement II is correct.
1. (i) µobs = µ x i
i i
whre µi is the dipole moment of a stable conformer of the molcule, Z – CH2 – CH2 – Z and xi is the mole fraction
of the stable conformer.
Given : µobs = 1.0 D and x (Anti) = 0.82
Draw all the stable conformers of Z – CH2 – CH2 – Z and calculate the value of µ(Gauche).
(ii) Draw the stable conformer of Y – CHD – CHD – Y (meso form), when Y = CH3 (rotation about C2 – C3) and
Y = OH (rotation about C1 – C2) in Newmann projection. [IIT 2005]
2. The correct statement (s) about the compound [IIT 2006]

H3C(HO) HC – CH = CH – CH(OH)CH3 (X) is/are
(A) The total number of stereoisomers possible for X is 6
(B) The total number of diastereomers possible for X is 3
(C) If the stereochemistry about the double bond in X is trans, the number of enantiomers possible for X is 4
(D) If the stereochemistry about the double bond in X is cis, the number of enantiomers possible for X is 2
3. The number of structural isomers for C6H14 is [IIT 2007]

(A) 3 (B) 4 (C) 5 (D) 6
4. Statement-1: Molecules that are not superimposable on their mirror images are chiral. because [IIT 2007]
Statement-2: All chiral moleculs have chiral centres.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1
(B) Statement-1 is true, statement-2 is true and statement-2 is NOT correct explanation for statement-1
(C) Statement-1 is true, statement-2 is false
(D) Statement-1 is false, statement-2 is true
5. The correct statement(s) about the compuond given below is (are) [IIT 2008]
Cl H
H3C
CH3
Cl H
(A) The compound is optically active

(B) The compound possesses centre of symmetry
(C) The compound possesses plane of symmetry
(D) The compound possesses axis of symmetry
6. The correct statement(s) concerning the structures E, F and G is (are) [IIT 2008]
H3C O H3C OH H3C CH3
(E) (F) (G)

H3C CH3 H3C CH3 H3C OH
(A) E, F and G resonance structures (B) E, F and E, G are tautomers
(C) F and G are geometrical isomers (D) F and G are diastereomers
7. The total number of cyclic structural as well as stereo isomers possible for compound with the molecular formular
C5H10 is [IIT 2009]
8. The total number of cyclic isomers possible for a hydrocarbon with the molecular formula C4H6 is [IIT 2010]
9. In the Newman projection for 2, 2-dimethylbutane X and Y cn respectively be [IIT 2010]
X
H3 C CH3
H H
Y
(A) H and H (B) H and C2H5 (C) C2H5 and H (D) CH3 and CH3
10. Amongst the given options, the compound(s) in which all the atoms are in one plane in all the possible conformations
(in any), is (are) [IIT 2011]
H H
H
C C
(A) (B) H C C C (C) H2C = C = O (D) H2C = C = CH2
H2C CH2
CH2
11. In Allene (C3H4), the type (s) of hybridisation of the carbon atoms is (are) [JEE Adv. 2012]
(A) sp and sp3 (B) sp and sp2 (C) only sp2 (D) sp2 and sp3
12. The number of optically active product obtained from the complete ozonolysis of the given compound is
CH3 H
CH3–CH=CH–C–CH=CH–C–CH=CH–CH
[JEE Adv. 2012]
H CH3
(A) 0 (B) 1 (C) 2 (D) 4
13. Which of the following molecules in pure from is (are) unstable at room temperature [JEE Adv. 2012]
O O
(A) (B) (C) (D)
14. Which of the given statement(s) about N, O, P and Q with respect to M is (are) correct ? [JEE Adv. 2012]
CH3 CH3
Cl
HO H HO H H H OH HO H
OH
HO Cl H CH3 HO
H OH H
HO H HO H
CH3 Cl CH3
Cl Cl
M N O P Q
(A) M and N are non-mirror image stereoisomers

(B) M and O are identical
(C) M and P are enantiomers
(D) M and Q are identical
15. The total number(s) of stable conformers with non-zero dipole moment for the following compound is (are).
Cl
Br CH3
Br Cl [JEE Adv. 2014]

CH3
16. Isomers of hexane, based on their branching, can be divided into three distinct classes as shown in the figure.
(I)
(II)
(III)
The correct order of their boiling point is :
(A) I > II > III (B) III > II > I (C) II > III > I (D) III > I > II
17. The correct combination of names for isomeric alcohols with molecular formula C4H10O is/are
(A) tert - butanol and 2 - methylpropan - 1 - ol [JEE Adv. 2014]
(B) tert - butanol and 1,1 - dimethylethan - 1-ol
(C) n - butanol and butan - 1 - ol
(D) iso - butyl alcohol and 2 - methylpropan - 1 - ol
18. The total number of stereoisomers that can exist for M is [JEE Adv. 2015]
H3 C CH3
H3C O
M
19. For the given compound X, the total number of optically active stereoisomers is_____.
OH H OH
H
* * [JEE Adv. 2018]
*
OH OH
( ) This type of bond indicates that he configuration at the specific carbon and the geometry of the double
bond is fixed.
( ) This type of bond indicates that he configuration at the specific carbon and the geometry of the double bond
is NOT fixed.
20. Total number of isomers, considering both structural and stereoisomers, of cyclic ethers with the molecular
formula C4H8O is ...... [JEE Adv. 2019]
21. Newman projections P, Q, R and S are shown below : [JEE Advance 2020]
Which one of the following options represents identical molecules ?

(A) P and Q (B) Q and S (C) Q and R (D) R and S
22. The Fischer projection of D-erythrose is shown below : [JEE Advance 2020]
D-Erythrose and its isomers are listed as P, Q, R, and S in Column-I. Choose the correct relationship of P, Q, R,
and S with D-erythrose from Column II.
Column – I Column – II
P. 1. Diastereomer
Q. 2. Identical
R. 3. Enantiomer
S.
(A) P  2, Q 3, R 2, S 2 (B) P  3, Q 1, R 1, S 2
(C) P  2, Q 1, R 1, S 3 (D) P  2, Q 3, R 3, S 1
23. The total number of chiral molecules formed from one molecule of P on complete ozonolysis (O3, Zn/
H2O) is ________. [JEE Advance 2022]
OH OH
HO HO OH
P
1. A 2. B 3. A 4. A 5. A 6. C 7. C
8. C 9. CD 10. A 11. A 12. A 13. B 24. B
15. 5 16. 2 17. 1 (Answer should be 1 and 3 both) 18. 3 19. D
20. B 21. D 22. 6 23. B 24. 60 25. D 26. D
27. (B) 28. C 29. C 30. 5/6 31. 3 32. A 33. 42
34. C

1
1. (i) D (ii) Anti form when Y = CH3 & Gauche when Y = -OH
0.18
2. AD 3. C 4. C 5. AD 6. BCD
7. 7 8. 5 9. BD 10. BC 11. B
12. A 13. BC 14. ABC 15. 3 16. B
17. ACD 18. 2 19. 7 20. 10 21. C
22. C 23. 2
GOC | JEE Main
1. Amongst the following the most basic compound is - [AIEEE-2005]

(A) aniline (B) benzylamine (C) p–nitroaniline (D) acetanilide
2. The number and type of bonds between two carbon atoms in calcium carbide are [AIEEE 2005]
(A) two sigma, two pi (B) two sigma, one pi (C) one sigma, two pi (D) one sigma, one pi
3. Due to the presence of an unpaired electron, free radicals are [AIEEE 2005]
(A) cations (B) anions (C) chemically inactive (D) chemically reactive
4. Among the following acids which has the lowest PKa value ? [AIEEE 2005]
(A) CH3CH2COOH (B) (CH2)2 CH – COOH
(C) HCOOH (D) CH3COOH
5. The increasing order of stability of the following free radicals is - [AIEEE 2006]
   
(A) (C6H5)3 C < (C6H5)2 C H < (CH3)3 C < (CH3)2 C H
   
(B) (C6H5)2 C H < (C6H5)3 C < (CH3)3 C < (CH3)2 C H
   
(C) (CH3)2 C H < (CH3)3 C < (C6H5)3 C < (C6H5)2 C H
   
(D) (CH3)2 C H < (CH3)3 C < (C6H5)2 C H < (C6H5)3 C
6. The correct order of increasing acid strength of the compound is : [AIEEE 2006]
Me
(a) CH3CO2H (b) MeOCH2CO2H (c) CF3CO2H (d) CO2H is
Me
(A) d < a < c < b (B) d < a < b < c (C) a < d < c < b (D) b < d < a < c
7. Which one of the following is the strongest base in aqueous solution ? [AIEEE-2007]
(A) Trimethylamine (B) Aniline (C) Dimethylamine (D) Methylamine
8. Presence of a nitro group in a benzene ring : [AIEEE 2007]

(A) activates the ring towards electrophilic substitution
(B) renders the ring basic
(C) deactivates the ring towards nucleophilic substitution
(D) deactivates the ring towards electrophilic substitution
9. Arrange the carbanions, (CH3)3 C , C Cl 3 , (CH3)2 C H , C6H5 C H 2 , in order of their decreasing stability -
(A) (CH3)2 C H > C Cl 3 > C6H5 C H 2 > (CH3)3 C [AIEEE 2009]
(B) C Cl 3 > C6H5 C H 2 > (CH3)2 C H > (CH3)3 C
(C) (CH3)3 C > (CH3)2 C H >C6H5 C H 2 > C Cl 3
(D) C6H5 C H 2 > C Cl 3 > (CH3)3 C > (CH3)2 C H

10. The correct order of increasing basicity of the given conjugate bases (R = CH3) is [AIEEE 2010]
–
(A) RCOO  HC  C  R  N H2 (B) R  HC  C  RCOO  N H2
(C) RCOO  NH2  HC  C  R– (D) RCOO  HC  C  N H2  R
11. The correct order of acid strength of the following compounds is : [AIEEE 2011]
A. Phenol B. p-Cresol C. m-Nitrophenol D. p-Nitrophenol
(A) D > C > A >B (B) B > D > A > C (C) A > B > D >C (D) C > B > A > D
12. The non aromatic compound among the following is - [AIEEE 2011]
(A) (B) (C) (D)

S
13. The order of stability of the following carbocations: [JEE Main 2013]
CH2
(I) CH2= CH – CH2 (II) CH3–CH2– CH2 (III) is :
(A) I > II > III (B) III > I > II (C) III > II > I (D) II > III > I
14. Considering the basic strength of amines in aqueous solution, which one has the smallest pKb value?
(A) CH3NH2 (B) (CH3)3N (C) C6H5NH2 (D) (CH3)2NH [JEE Main 2014]
15. Which of the following molecules is least resonance stabilized ? [JEE Main 2017]
(A) (B) N (C) (D)

O
O
16. The increasing order of basicity of the following compounds is : [JEE Main 2018]
NH2
(a) NH2 (b) NH (c) (d) NHCH3
NH
(A) (b) < (a) < (d) < (c) (B) (d) < (b) < (a) < (c)
(C) (a) < (b) < (c) < (d) (D) (b) < (a) < (c) < (d)
17. The predominant form of histamine present in human blood is (pKa, Histidine = 6.0) [JEE Main 2018]
H H
N
N
(A) (B) NH3
N NH2
H N
H H
N N
NH3
(C) NH2 (D)
N
N H
18. Which of the following compounds will show the maximum 'enol' content ? [JEE Main 2019]
(A) CH3COCH3 (B) CH3COCH2COCH3
(C) CH3COCH2COOC2H5 (D) CH3COCH2CONH2
19. Which amongst the following is the strongest acid ? [JEE Main 2019]
(A) CHBr3 (B) CHI3 (C) CHCl3 (D) CH(CN)3
20. The correct order for acid strength of compounds : [JEE Main 2019]
CH  CH, CH3 – C  CH and CH2 = CH2 is as follows :
(A) CH3 – C  CH > CH2 = CH2 > HC  CH
(B) CH3 – C  CH > CH  CH > CH2 = CH2
(C) HC  CH > CH3 – C  CH > CH2 = CH2
(D) CH  CH > CH2 = CH2 > CH3 – C  CH
21. Arrange the following labelled hydrogens in decreasing order of acidity : [JEE Main 2020]
(A) b > c > d > a (B) c > b > a > d (C) b > a > c > d (D) c > b > d > a
22. If you spill a chemical toilet cleaning liquid on your hand, your first aid would be: [JEE Main 2020]
(A) vinegar (B) aqueous NaOH (C) aqueous NaHCO3 (D) aqueous NH3
23. Which one of the following compounds possesses the most acidic hydrogen ? [JEE Main 2020]
(A) H3C – C  C – H (B)
(C) (D)
24. Consider the following molecules and statements related to them : [JEE Main 2020]
(A) (B)
(a) (B) is more likely to be crystalline than (A)

(b) (B) has higher boiling point than (A)
(c) (B) dissolves more readily than (A) in water
Identify the correct option from below :
(A) only (a) is true (B) (a) and (b) are true
(C) (b) and (c) are true (D) (a) and (c) are true
25. The decreasing order of reactivity of the following organic molecules towards AgNO3 solution is :
(A) (C) > (D) > (A) > (B) (B) (A) > (B) > (C) > (D) [JEE Main 2020]
(C) (B) > (A) > (C) >(D) (D) (A) > (B) > (D) > (C)
26. Among the following compounds, which one has the shortest C-Cl bond ? [JEE Main 2020]
(A) (B) (C) (D) H3C – Cl
27. Which of the following compounds will form the precipitate with aq. AgNO3 solution most readily ?
[JEE Main 2020]
(A) (B) (C) (D)
28. The increasing order of basicity of the following compounds is : [JEE Main 2020]
(A) (B) < (A) < (C) < (D) (B) (A) < (B) < (C) < (D)
(C) (D) < (A) < (B) < (C) (D) (B) < (A) < (D) < (C)
29. The increasing order of the acidity of the -hydrogen of the following compounds is : [JEE Main 2020]
(A) (C) < (A) < (B) < (D) (B) (B) < (C) < (A) < (D)
(C) (A) < (C) < (D) < (B) (D) (D) < (C) < (A) < (B)
30. The increasing order of boiling points of the following compounds is : [JEE Main 2020]
OH OH OH OH
CH3 NO2 NH2 OCH3

I II III IV
(A) I < IV < III < II (B) IV < I < II < III (C) I < III < IV < II (D) III < I < II < IV
31. The increasing order of pKb values of the following compounds is : [JEE Main 2020]
N(CH3) 2
N(CH3) 2 NHCH3 NHCH3
(I) (II) (III) (IV)

CN OH
OCH3
(A) II < I < III < IV (B) II < IV < III < I (C) I < II < IV < III (D) I < II < III < IV
32. Which one of the following compounds is non-aromatic ? [JEE-Mains (24-Feb_Shift -2)2021]
(A) (B) (C) (D)

O
33. The correct order of acid character of the following compounds is :
(A) II>III>IV>I (B) III>II>I>IV (C) IV>III>II>I (D) I>II>III>IV
34. A. Phenyl methanamine B. N, N-Dimethylaniline [JEE-Mains (26-Feb_Shift -2)2021]

C. N-Methyl aniline D. Benzenamine
Choose the correct order of basic nature of the above amines.
(A) D > C > B > A (B) D > B > C > A
(C) A > C > B > D (D) A > B > C > D
35. In the following molecule, [JEE-Mains (18-March_Shift -1)2021]

a
H3 C
b c
C=C–O
H H
Hybridisation of Carbon a, b and c respectively are :

(A) sp3, sp2, sp2 (B) sp3, sp2, sp (C) sp3, sp, sp (D) sp3, sp, sp2
36. Among the following, the aromatic compounds are: [JEE-Mains (16-March_Shift -1)2021]
(A) (B) (C) (D)
Choose the correct answer from the following options:

(A) (A) and (B) only (B) (A), (B) and (C) only
(C) (B), (C) and (D) only (D) (B) and (C) only
37. Assertion A :Enol form acetone [CH3COCH3] exists in <0.1% quantity. However, the enol form the acetyl
acetone [CH3COCH2OCCH3] exists in approximately 15% quantity.
Reason R: Enol form of acetyl acetone is stabilized by intramolecular hydrogen bonding, which is not possible
in enol form of acetone. [JEE-Mains (16-March_Shift -1)2021]
Choose the correct statement:
(A) A is true but R is false
(B) Both A and R are true but R is the correct explanation of A
(C) A is false but R is true
(D) Both A and R are true but R is not the correct explanation of A
38. The INCORRECT statement regarding the structure of C60 is: [JEE-Mains (16-March_Shift -2)2021]
(A) It contains 12 six-membered rings and 24 five-membered rings.
(B) Each carbon atom forms three sigma bonds.
(C) The five-membered rings are fused only to six-membered rings.
(D) The six-membered rings are fused to both six and five-membered rings.
39. Statement-I: Sodium hydride can be used as an oxidising agent.

Statement-II: The lone pair of electrons on nitrogen in pyridine makes it basic:
Choose the CORRECT answer from the options given below:
(A) Statement I is true but statement II is false [JEE-Mains (16-March_Shift -2)2021]
(B) Both statement I and statement II are false
(C) Both statement I and statement II are true
(D) Statement I is false but statement II is true
40. Which of the following is least basic? [JEE-Mains (16-March_Shift -2)2021]

••
(A) (CH3CO)2 •• (B) (CH3CO) N H C2H5
NH
(C) (C2H5)3 •• (D) (C2H5)2 ••
N NH
41. Which of the following is an aromatic compound ? [JEE-Mains (17-March_Shift -1)2021]


–
(A) – (B) (C) (D)
–
 
CH 2 CH2  
CH 2 CH
42.
H O
(A) (B) (C) (D) [JEE-Mains (20-July_Shift -1)2021]

Among the given species the Resonance stabilised carbocations are:
(A)(C) and (D) only (B) (A), (B) and (C) only
(C)(A), (B) and (D) only (D)(A) and (B) only
43. Metallic sodium does not react normally with: [JEE-Mains (20-July_Shift-2)2021]
(A) tert-butyl alcohol (B) But-2-yne
(C) Ethyne (D) gaseous ammonia
44. Which one of the following compounds does not exhibit resonance ? [JEE-Mains (22-July_Shift-2)2021]
CH2OH
(A) CH 3CH2CH2CONH 2 (B)
(C) CH3CH2OCH = CH2 (D) CH3CH2CH = CHCH2NH2
45. Which purification technique is used for high boiling organic liquid compound (decomposes near its boiling point)
? [JEE-Mains (22-July_Shift-2)2021]
(A) Steam distillation (B) Simple distillation
(C) Fractional distillation (D) Reduced pressure distillation
46. Which one of the following compounds will liberate CO2, when treated with NaHCO3?
   
(A)  CH3  N O H (B)  CH3  NHC l [JEE-Mains (25-July_Shift -1)2021]
4 3
(C) CH3NH2 (D) CH3 C NH2
47. Which one among the following resonating structures is not correct? [JEE-Mains (25-July_Shift -1)2021]
 O
 O 
N  N

(A) (B) 
O O
O   O

 N N


(C) O (D)
O
48. Identify the species having one -bond and maximum number of canonical forms from the following :
(A) CO2–
3
(B) O2 (C) SO2 (D) SO3
49. The correct decreasing order of densities of the following compounds is:[JEE-Mains (25-July_Shift-2)2021]
Cl Br
Cl
Cl Cl
(A) (B) (C) (D)
(A) (D) > (C) > (B) > (A) (B) (C) > (B) > (A) > (D)
(C) (C) > (D) > (A) > (B) (D)(A) > (B) > (C) > (D)
50. Which among the following is the strongest acid ? [JEE-Mains (25-July_Shift-2)2021]
(A) (B) (C) (D)CH 3CH 2CH 2CH 3
+
CH2
+ + +
51. CH2=CH CH 3–CH 2 HC C [JEE-Mains (27-July_Shift-1)2021]
A B C D
The correct order of stability of given carbocation is :

(A) C > A > D > B (B) D > B > C > A (C) A > C > B > D (D) D > B > A > C
52. Given below are two statements: [JEE-Mains (27-July_Shift-1)2021]

Statement I :Aniline is less basic than acetamide.
Statement II :In aniline, the lone pair of electrons on nitrogen atom is delocalised over benzene ring due to
resonance and hence less available to a proton.
Choose the most appropriate option;
(A) Both statement I and statement II are true.
(B) Both statement I and statement II are false.
(C) Statement I is true but statement II is false.
(D) Statement I is false but statement II is true.

Statement I: Hyperconjugation is a permanent effect.

 
Statement II: Hyper conjugation in ethyl cation  CH3  CH2  involves the over lapping of C sp2  H1s bond with empty
 
2p orbital of other carbon.
Choose the correct option:
(A) Both statement I and statement II are true
(B) Statement I is incorrect but statement II is true
(C) Statement I is correct but statement II is false
(D) Both Statement I and statement II are false.
54. Which one of the following compounds is not aromatic? [JEE-Mains (26-August_Shift-2)2021]
O
H
(A) (B) (C) (D)

55. The compound/s which will show significant intermolecular H-bonding is/are :
NO2
H
OH CH 3
N
O
OH OH
(a) (b)
(c)
(A) (c) only (B) (b) only

(C) (a) and (b) only (D) (a), (b) and (c)
56. Given below are two statements : one is labelled as Assertion (A) and the other is labelled as Reason (R).
Assertion (A) : A simple distillation can be used to separate a mixture of propanol and propanone.
Reason (R) : Two liquids with a difference of more than 20oC in their boiling points can be separated by simple
distillations. [JEE-Mains (31-August_Shift-1)2021]
In the light of the above statements, choose the most appropriate answer from the
options given below:
(A) Both (A) and (R) are correct but (R) is not the correct explanation of (A).
(B) (A) is false but (R) is true.
(C) (A) is true but (R) is false
(D) Both (A) and (R) are correct and (R) is the correct explanation of (A).
57. Which one of the following compounds is aromatic in nature ?

[JEE-Mains (1-September_Shift-2)2021]
CH3
+
(A) (B) (C) (D)
58. Which of the following is an example of conjugated diketone? [JEE-Mains (24-Jun-Shift-1)2022]

O
CH2 O
(A) (B) CH2 C CH2 O
CH3 C CH2 CH2 CH2 C CH3
O
O
CH2 CH2 C CH3

(C) O O (D)
59. The major product ‘A’ of the following given reaction has_____sp2 hybridized carbon atoms.

H
2,7-Dimethyl1-2, 6 –octadiene   A
Major Product
60. Which of the following structures are aromatic in nature ? [JEE-Mains (28-Jun-Shift-1)2022]

(A) (B) (C) (D)
(A) A, B, C and D (B) Only A and B (C) Only A and C (D) Only B, C and D
61. Which of the following carbocations is most stable? [JEE-Mains (29-Jun-Shift-2)2022]

OCH 3 OCH3
(A) (B) (C) H3CO 
(D) H CO 
3
 
62. Arrange the following in decreasinog acidic strength. [JEE-Mains (25-July_Shift-2)2022]

OH OH OH OH
NO2 OCH3
NO2 OCH3
(A) (B) (C) (D)
(A) A > B > C > D (B) B > A > C > D (C) D > C > A > B (D) D > C > B > A
63. Which of the following compounds is not aromatic ? [JEE-Mains (26-July_Shift-1)2022]
H H
(A) (B) (C) (D)

64. Which of the following is not an example of benzenoid compound ?

NH2
(A) (B) (C) (D)
65. Given below are two statements : one is labelled as Assertion A and, the other is labelled as Reason R.
Assertion A : [6] Annulene, [8] Annulene and cis-[10] Annulene, are respectively aromatic,
not-aromatic and aromatic. [JEE-Mains (27-July_Shift-1)2022]
H H
[6] Annulene [8] Annulene cis - [10] Annulene

Reason R : Planarity is one of the requirements of aromatic systems
In the light of the above statements, choose the most appropriate answer from the options given
below.
(A) Both A and R are correct and R is the correct explanation of A.
(B) Both A and R are correct but R is NOT the correct explanation of A
(C) A is correct but R is not correct
(D) A is not correct but R is correct
66. Among the following marked proton of which compound shows lowest pKa value ?
H H O
(A) H2C COOH (B) H2C C CH3
H H
CH3 OH
(C) (D)
O O
67. Which among the following is the strongest Bronsted base?

H3C H3C
CH3
CH2 CH 2
N
N
N CH3 N
(A) H2C (B) H2C (C) (D)
CH2 H
CH3 CH3
1. For 1-Methoxy-1,3-butadiene, which of the following resonating structure is the least stable ? [IIT-2005]
(A) H2C – CH – CH = CH – O – CH 3 (B) H2C – CH = CH – CH = O – CH 3
(C) H2C = CH = CH – CH – O – CH 3 (D) H2C = CH – CH – CH = O – CH 3
2. Predict whether the following molecules are iso structural or not. Justify your answer. [IIT-2005]
(i) NMe3 (ii) N(SiMe3)3
3. When benzene sulfonic acid and p-nitrophenol are treated with NaHCO3, the gases released respectively are
(A) SO2,NO2 (B) SO2,NO (C) SO2,CO2 (D) CO2,CO2 [IIT-2006]
4. (I) 1, 2-dihydroxy beznene (II) 1, 3-dihydroxy benzene

(III) 1, 4-dihydroxy benzene (IV) Hydroxy benzene
The increasing order of boiling points of above mentioned alcohols is [IIT-2006]
(A) I < II < III < IV (B) I < II < IV < III (C) IV < I < II < III (D) IV < II < I < III
5. Among the following, the least stable resonance structure is : [IIT-2007]
O O
O O N N
(A) N (B) N (C) (D)
O O
O O
6. Statement-1: p-Hydroxybenzoic acid has a lower boiling point then o-hydroxybenzoic acid. [IIT-2007]
Statement-2: o-Hydroxybenzoic acid has a intramoleculer hydrogen bonding.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1.
(B) Statement-1 is true, statement-2 is true and statement-2 is NOT correct explanation for statement-1.
(C) Statement1 is true, statement-2 is false.
(D) Statement1 is false, statement-2 is true.
7. Hyperconjugation involves overlap of the following orbitals [IIT-2008]

(A)  –  (B)  – p (C) p – p (D)  – 
8. The correct stability order for the following species is [IIT-2008]
(I) (II) (III) (IV)

O O
(A) II > IV > I > III (B) I > II > III > IV (C) II > I > IV > III (D) I > III > II > IV
9. The correct acidity order of the following is [IIT-2009]
COOH
OH OH COOH
(I) (II) (III) (IV)
CH3
Cl
(A) III > IV > II > I (B) IV > III > I > II (C) III > II > I > IV (D) II > III > IV > I
10. The correct stability order of the following resonance structures is [IIT-2009]
+ – + – – + – +
(I) H2C = N = N (II) H2C – N = N (III) H2C – N = N (IV) H2C – N = N
(A) I > II > IV > III (B) I > III > II > IV (C) II > I > III > IV (D) III > I > IV > II
11. In the following carbocation; H/CH3 that is most likely to migrate to the positively charged carbon is
[IIT-2009]
H H
1 2 + 4 5
H3C – C – C – C –CH3
3
OH H CH3
(A) CH3 at C-4 (B) H at C-4 (C) CH3 at C-2 (D) H at C-2
12. The total number of basic group in the following form of lysine is : [IIT-2010]
O
+
NH3 – CH2 – CH2 – CH2 – CH2 – CH – C
–
O
NH2
13. Amongst the following, the total number of compounds soluble in aqueous NaOH is [IIT-2010]
H3C CH3
N COOH NO2 OH
N
H3C CH 3
14. Among the following compounds, the most acidic is: [IIT-2011]
(A) p-nitrophenol (B) p-hydroxybenzoic acid
(C) o-hydroxybenzoic acid (D) p-toluic acid
15. The total number of contrubting structure showing hyperconjugation (involving C-H bonds) for the following
carbocation is [JEE-2011]
CH3 CH2CH3
16. In Allen (C3H4), the type (s) of hybridisation of the carbon atoms is (are) [JEE Adv. 2012]
17. Which of the following molecules in pure from is (are) unstable at room temperature [JEE Adv. 2012]
O O
(A) (B) (C) (D)
18. The compound that does NOT liberate CO2, on treatment with aqueous solium bicarbonate solution is
(A) Benzoic acid (B) Benzenesulphonic acid [JEE Adv. 2013]
(C) Salicylic acid (D) Carbolic acid (Phenol)
19. The hyperconjugative stabilities of tert-butyl cation and 2-butene, respectively, are due to [JEE Adv. 2013]
(A)   p (empty) and    electron delocalisations
(B)    and    electron delocalisations
(C)   p (filled) and    electron delocalisations
(D) p (filled)  and    electron delocalisations
20. The number of resonance structures for N is : [JEE Adv. 2015]

OH
NaOH
N
21. The correct order of acidity for the following compounds is : [JEE Adv. 2016]
CO2H
CO2H
CO2H CO2H
HO OH OH
(I) (II) (III) (IV)
OH
OH
(A) I > II > III > IV (B) III > I > II > IV (C) III > IV > II > I (D) I > III > IV > II
22. Among the following the number of aromatic compound(s) is : [JEE Adv. 2017]
23. The order of basicity among the following compounds is : [JEE Adv. 2017]
NH NH2
(I) (II) N NH (III) HN N (IV)
H3C NH 2 H 2N NH
(A) IV > II > III > I (B) II > I > IV > III (C) I > IV > III > II (D) IV > I > II > III
24. The correct order of acid strength of the following carboxylic acids is : [JEE Adv. 2019]
O
O H O
OH OH
I. H II. III. MeO IV. H3C
OH O
OH H
(A) II > I > IV > III (B) III > II > I > IV (C) I > II > III > IV (D) I > III > II > IV
25. With respect to the compounds I–V, choose the correct statement(s). [JEE Advance 2020]
(A) The acidity of compound I is due to delocalization in the conjugate base.

(B) The conjugate base of compound IV is aromatic.
(C) Compound II becomes more acidic, when it has a –NO2 substituent.
(D) The acidity of compounds follows the order I > IV > V > II > III.
26. Consider the following four compounds I, II, III, and IV. [JEE Advance 2020]
I II III IV
Choose the correct statement(s).
(A) The order of basicity is II > I > III > IV.
(B) The magnitude of pKb difference between I and II is more than that between III and IV.
(C) Resonance effect is more in III than in IV
(D) Steric effect makes compound IV more basic than III.
1. B 2. C 3. D 4. C 5. D 6. B 7. C
8. D 9. B 10. D 11. A 12. D 13.. B 14. D
15. C 16. A 17. B 18. B 19. D 20. C 21. A
22. C 23. C 24. B 25. C 26. B 27. A 28. D
29. D 30. A 31. C 32. B 33. A 34. D 35. A
36. D 37. B 38. A 39. D 40. A 41. A 42. D
43. B 44. D 45. D 46. B 47. D 48. A 49. A
50. A 51. C 52. D 53. C 54. A 55. B 56. A
57. A 58. C 59. 2 60. B 61. D 62. A 63. C

64. AB 65. D 66. C 67. D

1. C
SiMe3
N N
2. Me Me SiMe3 SiMe3
Me
(Pyramidical)
Given componds are not isostrucutral

Delocalised of l.p. of nitrogen in vacant d-orbital of silicon makes compound planar.
3. D 4. C 5. A 6. D 7. B 8. D 9. A
10. B 11. D 12. 2 13. 4 14. C 15. 6 16. B
17. B 18. D 19. A 20. 9 21. A 22. 5 23. D
24. C 25. ABC 26. CD

Hydrocarbon | JEE Main
1. Reaction of one molecule of HBr with one molecule of 1,3–butadiene at 40ºC given predominantly [AIEEE-2005]
(A)1–bromo–2–butene under thermodynamically controlled conditions
(B) 3–bromobutene under kinetically controlled conditions
(C) 1–bromo–2–butene under kinetically controlled conditions
(D) 3–bromobutene under thermodynamically controlled conditions
2. Acid catalyzed hydration of alkenes except ethene leads to the formation of– [AIEEE-2005]
(A) secondary or tertiary alcohol (B) primary alcohol
(C) mixture of secondary and tertiary alcohols (D) mixture of primary and secondary alcohols
3. Alkyl halides react with dialkyl copper reagents to give [AIEEE-2005]

(A) alkyl copper halides (B) alkenes (C) alkenyl halides (D) alkanes
4. Elimination of bromine from 2–bromobutane results in the formation of – [AIEEE-2005]

(A) predominantly 2–butene (B) equimolar mixture of 1 and 2–butene
(C) predominantly 2–butyne (D) predominantly 1–butene
5. 2 - methyl butane on reacting with bromine in the presence of sunlight gives mainly [AIEEE 2005]
(A) 1 - bromo - 3 - methybutane (B) 2 - bromo - 3 - methylbutane
(C) 2 - bromo - 2 - methylbutane (D) 1 - bromo - 2 - methylbutane
6. Of the five isomeric hexanes, the isomer which can give two monochlorinated compounds, is
(A) 2 - methylpentane (B) 2, 2 - dimethylbutane [AIEEE 2005]
(C) 2, 3 - dimethylbutane (D) n - hexane
Me

Me
7.  N 
OH 
n-Bu Et
The alkene formed as a major product in the above elimination reaction is [AIEEE 2006]
Me Me
(A) CH2 = CH2 (B) (C) (D) Me
8. Fluorobenzene (C6H5F) can be synthesized in the laboratory - [AIEEE 2006]

(A) from aniline by diazotisation followed by heating the diazonium salt with HBF4
(B) by direct fluorination of benzene with F2 gas
(C) by reacting bromobenzene with NaF solution
(D) by heating phenol with HF and KF
9. Phenyl magnesium bromide reacts with methanol to give - [AIEEE 2006]

(A) a mixture of benzene and Mg(OMe) Br (B) a mixture of toluene and Mg(OH)Br
(C) a mixture of phenol and Mg(Me)Br (D) a mixture of anisole and Mg(OH) Br
10. HBr reacts with CH2 = CH – OCH3 under anhydrous conditions at room temperature to give [AIEEE 2006]
(A) CH3CHO AND CH3Br (B) BrCH2CHO and CH3OH
(C) BrCH2 – CH2 – OCH3 (D) H3C – CHBr – OCH3
11. Trans - 2 phenyl 1 - bromocyclopenta ne on reaction with alcoholic KOH produces [AIEEE 2006]
(A) 4 - phenylcyclopentene (B) 2 - phenylcyclopentene
(C) 1 - phenylcyclopentene (D) 3 - phenylcyclopentene
12. CH3Br + Nu–  CH3 – Nu + Br– [AIEEE 2006]

The decreasing order of the rate of the above reaction with nucleophile (Nu ) A and D is
–
[Nu = (A) PhO–, (B) AcO–, (C) HO–, (D)CH3O–]

(A) D > C > A > B (B) D > C > B > A (C) A > B > C > D (D) B > D > C > A
13. Which of the following reactions will yield 2, 2-dibromopropane ? [AIEEE 2007]
(A) CH3 – C  CH + 2HBr  (B) CH3CH = CHBr + HBr 
(C) CH  CH + 2HBr  (D) CH3 – CH = CH2 + HBr 
14. Presence of a nitro group in a benzene ring [AIEEE 2007]

(A) activates the rin towards elecrophillic substitution
(B) renders the ring basic
(C) deactivates the ring towards nucleophillic substitution
(D) deactivities the ring towards electrophillic substitution.
15. The reactions to toluene with Cl2 in presence of FeCl3 gives predominantly [AIEEE 2007]
(A) benzoyl chloride (B) benzyl chloride
(C) o - and p - chlorotoluene (D) m - chlorotoluene
16. In the following sequence of reactions, the alkene affords the compound ‘B’
H 2O
CH3CH = CHCH3 
O3 A  B, The compound B is
Zn
[AIEEE 2008]
(A) CH3COCH3 (B) CH 3CH2COCH 3 (C) CH3CHO (D) CH3CH2CHO
17. The treatment of CH3MgX with CH3CC–H produces [AIEEE 2008]

H H
| |
(A) CH3CC–CH 3 (B) CH3 – C = C – CH3 (C) CH4 (D) CH3–CH=CH2
18. The hydrocarbon which can react with sodium in liquid ammonia is - [AIEEE 2008]
(A) CH3CH2CCH (B) CH3CH=CHCH3
(C) CH 3CH2CCCH2CH3 (D) CH3CH2CH2CCCH2CH2CH3
19. The organic chloro compound, which shows complete stereochemical inversion during an SN2 reaction is
(A) (C2H5)2 CHCl (B) (CH3)3 CCl (C) (CH3)2 CHCl (D) CH3Cl [AIEEE 2008]
20. The electrophile, E+ attacks the benzene ring to generate the intermediate  - complex which of the following -
complex is of lowest energy? [AIEEE 2008]
NO2
NO2 NO2
H H
+
(A) + (B) (C) + E (D) + E
H
E
H E
21. One mole of a symmetrical alkene on ozonolysis gives two moles of an aldehyde having a molecular mass of 44u.
The alkene is [AIEEE 2010]
(A) propene (B) 1 - butene (C) 2-butene (D) ethene
22. Consider the following bromides, [AIEEE 2010]
Me Me
(A) Me Br
(B) (C) Me
Br Br
The correct order of SN1 reactivity is
(A) (B) > (C) > (A) (B) (B) > (A) > (C) (C) (C) > (B) > (A) (D) (A) > (B) > (C)
23. Ozonolysis of an organic compounds gives formaldehyde as one of the products. This confirms the presence of :
(A) two ethylenic double bonds (B) vinyl group [AIEEE 2011]
(C) an isopropyl group (D) an acetylenic triple bond
24. Ozonolysis of an organic compound ‘A’ produces acetone and propionaldehyde in equimolar mixture. Identify ‘A’
from the following compounds [AIEEE 2011]
(A) 1 - Pentene (B) 2 - Pentene
(C) 2 - Methyl - 2 - pentene (D) 2 - Methyl - 1 – pentene
25. The non - aromatic compound among the following is [AIEEE 2011]
(A) (B) (C) (D) None of these

S
26. 2-Hexyne gives trans -2- Hexene on treatment with - [JEE Main 2012]
(A) Li/NH3 (B) Pd/BaSO4 (C) LiAlH4 (D) Pt/H2
27. Which branched chain isomer of the hydrocarbon with molecular mass 72u gives only one isomer of mono
substituted alkyl halide ? [JEE Main 2012]
(A) Neopentane (B) Isohexane (C) Neohexane (D) Tertiary butyl chloride
28. How many chiral compounds are possible on monochlorination of 2-methyl butane? [JEE Main 2012]
(A) 8 (B) 2 (C) 4 (D) 6
29. Iodoform can be prepared from all except [JEE Main 2012]
(A) ethyl methyl ketone (B) isopropyl alcohol
(C) 3-methyl - 2 - butanone (D) isobutyl alcohol
30. Compound (A), C8H9Br gives a white precipitate when warmed with alcoholic AgNO3, Oxidation of (A) gives an
aicd (B), C8H6O4. (B) easily forms anhydride on heating.Identify the compound (A). [JEE Main 2013]
CH2Br
CH2Br CH2Br CHB2 r
(A) (B) (C) (D)
Br CH 3
CH3 CH3
31. A solution of (–1) - choloro 1 - phenylethane in toluene recemises slowly in the presence of a small amount of
SbCl5, due to the formation of [JEE Main 2013]
(A) carbanion (B) carbene (C) carbocation (D) free radical
32. The major organic compound formed by the reaction of 1,1,1-trichloroethane with silver powder is ?
[JEE Main 2014]
(A) 2 Butyne (B) 2 - Butene (C) Acetylene (D) Ethene
33. Which compound would give 5 - keto - 2 - methyl hexanal upon ozonolysis ? [JEE Main 2015]
CH 3 CH3
CH3 CH3
H3C CH3
(A) (B) (C) (D)
CH3 CH3
34. The reaction of propene with HOCl (Cl2 +H2O) proceeds through the intermediate : [JEE Main 2016]
(A) CH3 — CH+ — CH2 — Cl (B) CH3 —CH(OH) —CH2+
+
(C) CH3—CHCl — CH2 (D) CH3 — CH+ — CH2 — OH
35. The product of the reaction given below is : [JEE Main 2016]
(A) (B) (C) (D)
36. Which of the following compounds will behave as a reducing sugar in an aqueous KOH solution ?
[JEE Main 2017]
HOH 2C
O CH 2OCH 3
OH
(A) (B) (C) (D)
OH
OH
37. The major product obtained in the following reaction is : [JEE Main 2017]
Br
H
tBuOK
C6H5
C6H5 (+)
(A) C6H5CH = CHC6H5 (B) (+)C6H5CH(OtBu) CH2C6H5
(C) (–)C6H5CH(OtBu)CH 2C6H5 (D) (±)C6H5CH(OtBu)CH 2C6H5
38. The trans-alkenes are formed by the reduction of alkynes with : [JEE Main 2018]
(A) Sn – HCl (B) H2 – Pd/C, BaSO4 (C) NaBH4 (D) Na/liq. NH3
39. The major product in the following reaction is : [JEE MAIN 2020]
(A) (B) (C) (D)

40. The major product of the following reaction is: [JEE MAIN 2020]
OH
CH3
Conc. HNO3 + Conc. H2SO4
NO2
OH
OH OH OH
CH3
CH3 NO2 CH3 NO2 CH3
(A) (B) (C) NO2 (D)
NO2 NO2 O2 N NO2
NO2
41. Zon hydrogenation ?

[JEE MAIN 2020]
(A) (B) (C) (D)
42. The total number of monohalogenated organic products in the following (including stereoisomers) reaction
is__________. [JEE MAIN 2020]
43. [P] on treatment with Br2/FeBr3 in CCl4 produced a single isomer C8H7O2Br while heating [P] with sodalime gas
toluene. The compound [P] is : [JEE MAIN 2020]
(A) (B) (C) (D)
44. The major product [C] of the following reaction sequence will be : [JEE MAIN 2020]
(A) (B) (C) (D)
45. In the following reaction sequence the major product A and B are : [JEE MAIN 2020]
(A) A = ;B= (B) A = ;B=
(C) A = ;B= (D) A = ;B=
46. The final major product of the following reaction is : [JEE MAIN 2020]
Me
(i) Ac2O/ Pyridine
(ii) Br2 , FeCI3
(iii) OH- / 
NH2
Br
Me Me Br Me
Me
(A) (B) Br (C) (D) Br

NH2 NH2 NH2
NH2
47. The major product of the following reaction is : [JEE MAIN 2020]
CH3
2HBr
NO2
CH3 CH3 Br CH3

H3C Br
Br Br
(A) (B) (C) (D)

Br Br
Br Br
NO2 NO2 CH3
NO2
48. The major product obtained from the following reaction is : [JEE MAIN 2020]
+2 +
Hg |H
O2 N C C OCH 3
H2O
OCH 3 OH
O O
(A) (B)
O2N O2N
OCH 3 OH
(C) (D)
O O
O 2N O 2N
49. The increasing order of the boiling points of the major product A, B and C of the following reactions will be
[JEE MAIN 2020]
(a) (b) (c)

(A) A < B < C (B) A < C < B (C) B < C < A (D) C < A < B
50. Which one of the following carbonyl compounds cannot be prepared by addition of water on an alkyne in the
presence of HgSO4 and H2SO4 ? [JEE-Mains (February_Shift -1)2021]
O O
|| ||
(A) CH3  CH2  C  H (B) C  CH3
O O
|| ||
(C) CH3  C  H (D) CH3
 C  CH2CH3
51. The major product of the following reaction is : [JEE-Mains (25-Feb_Shift -2)2021]
NO2
H 2 SO4
NO2 NO2 NO2

NO2
(A) (B) (C) (D)
52. Identify A in the given chemical reaction. [JEE-Mains (26-Feb_Shift -2)2021]
CH3
CH2
Mo2O3
CH3 'A'
CH2 773 K, 10-20 atm
CH major product
CH2 CH3
CH3 HCH3
(A) (B) (C) (D)
53. Which of the following is Lindlar catalyst ? [JEE-Mains (16-March_Shift -1)2021]

(A) Zinc chloride and HCl (B) Partially deactivated palladised charcoal
(C) Sodium and Liquid NH3 (D) Cold dilute solution of KMnO4
54. Match List-I with List-II: [JEE-Mains (16-March_Shift -2)2021]
List-I List-II
Test/Reagents/Observation(s) Species detected
(a) Lassaigne’s Test (i) Carbon
(b) Cu(II) oxide (ii) Sulphur
(c) Silver nitrate (iii) N, S, P and halogen
(d) The sodium fusion extract gives black (iv) Halogen Specifically
precipitate with acetic acid & lead acetate
The correct match is:
(A) (a)-(iii), (b)-(i), (c)-(iv), (d)-(ii)
(B) (a)-(i), (b)-(iv), (c)-(iii), (d)-(ii)
(C) (a)-(iii), (b)-(i), (c)-(ii), (d)-(iv)
(D) (a)-(i), (b)-(ii), (c)-(iv), (d)-(iii)
55. An unsaturated hydrocarbon X on ozonolysis gives A. Compound A when warmed with ammonical silver nitrate
forms a bright silver mirror along the sides of the test tube. The unsaturated hydrocarbon X is:
[JEE-Mains (16-March_Shift -2)2021]
CH3
(A) CH3–CC–CH3 (B) CH3C  C CH3 (C) HCC–CH2–CH3 (D) CH3—C=

| |
CH3CH3
CH3 COOH
56. " A" [JEE-Mains (16-March_Shift -2)2021]
 

OCH3 OCH3
In the above reaction, the reagent “A” is:
(A) NaBH4, H3O+ (B)HCl, Zn–Hg (C) Alkaline KMnO4, H+ (D) LiAlH4
CH 3
Alkaline KMnO4
57. “X” [JEE-Mains (18-March_Shift -1)2021]
+
H
OCH3
Considering the above chemical reaction, identity the product “X” :
CH3 CHO COOH

CH2OH
(A) X – (B) X – (C) X – (D) X –
OH OCH3 OCH3
OCH3
KMnO4 ‘A’
(major product)
H 2SO4,
58. KMnO4 ‘B’

[JEE-Mains (20-July_Shift -1)2021]
H 2O, 273K (major product)
For above chemical reactions, identify the correct statement from the following:
(A) Compound’A’is dicarboxylic acid and compound ‘B’ is diol
(B) Compound ‘A’ is diol and compound ‘B’ is dicarboxylic acid
(C) Both compound ‘A’ and compound ‘B’ are diols
(D) Both compound ‘A’ and compound ‘B’ are dicarboxylic acids
59. An Organic compound ‘A’ C4H8 on treatment with KMnO4/H+ yields compound ‘B’ C3H6O.
Compound ‘A’ also yields compound ‘B’ an ozonolysis. Compound ‘A’ is :
(A) But-2-ene [JEE-Mains (25-July_Shift -1)2021]
(B) 2-Methylpropene
(C) Cyclobutane
(D) 1-Methylcyclopropane
H3C H
CCl4
+ Br2 
60.  Product “P” [JEE-Mains (25-July_Shift-2)2021]
H 3C H
Consider the above chemical reaction. The total number of stereoisomers possible for product ‘P’ is
_____________.
61. Presence of which reagent will affect the reversibility of the following reaction, and change it to a irreversible
reaction : [JEE-Mains (27-July_Shift-1)2021]
hv
CH 4  I 2 CH 3  I  HI
Reversible
(A) HOCl (B) LiquidNH3 (C) diluteHNO2 (D) Concentrated HIO3
62. Which one of the following set of elements can be detected using sodium fusion extract?
(A) Halogens, Nitrogen, Oxygen,Sulfur [JEE-Mains (27-July_Shift-2)2021]
(B) Sulfur, Nitrogen, Phosphorous,Halogens
(C) Nitrogen, Phosphorous, Carbon,Sulfur
(D) Phosphorous, Oxygen, Nitrogen,Halogens
63. Excess of isobutane on reactions with Br2 in presence of light at 125ºC gives which one of the following, as the
major product ? [JEE-Mains (26-August_Shift-1)2021]
CH 3 Br
(A) CH3 –C–Br (B) CH 3–CH–CH 2–Br (C) CH 3–CH–CH2 –Br (D) CH3–C–CH 2–Br
CH 3 CH3 CH2–Br CH 3
64. The major product formed in the following reactions is : [JEE-Mains (26-August_Shift-1)2021]
HBr Major Product
Br Br
Br
(A) Br (B) (C) (D) Br
Br
65. Among the following compounds I-IV, which one forms a yellow precipitate on reacting sequentially with (i)
NaOH (ii) dil. HNO3 (iii) AgNO3? [JEE-Mains (26-August_Shift-1)2021]
Cl Cl Br Cl
H3C CH3 CH2I

CH3
I II III IV
(A) III (B) IV (C) II (D) I
66. Given below are two statements : one is labelled as Assertion (A) and the other is labelled as Reason (R).
Assertion (A) : Treatment of bromine water propene vields 1-bromopropan-2-ol.
Reason (R) : Attack of water on bromonium ion follows Markovnikov rule and results in 1-bromopropan-2-ol.
In the light of the above statements, choose the most appropriate answer from the
options given below. `[JEE-Mains (31-August_Shift-1)2021]
(A) Both (A) and (R) are true but (R) is NOT the correct explanation of (A).
(B) (A) is false but (R) is true.
(C) (A) is true but (R) is false.
(D) Both (A) and (R) are true and (R) is the correct explanation of (A).
67. The stereoisomers that are formed by electrophilic addition of bromine to trans-but-2-ene is /are :
(A) 2 enantiomers [JEE-Mains (1-September_Shift-2)2021]
(B) 2 enantiomers and 2 mesomers
(C) 2 identical mesomers
(D) 1 racemic and 2 enantiomers
68. Given below are two statements. [JEE-Mains (24-Jun-Shift-2)2022]

Statement I: The presence of weaker -bonds make alkenes less stable than alkanes.
Statement II: The strength of the double bond is greater than that of carbon-carbon single bond.
In the light of the above statements, choose the correct answer from the options given below:
69. Which of the following reagents /reactions will convert ‘ A ‘ to ‘ B ‘?

CH2 CHO
H3C H3C
(A) (B)
(A) PCC oxidation [JEE-Mains (24-Jun-Shift-2)2022]
(B) Ozonolysis
(C) BH3,H2O2/OHfollowed by PCC oxidation
(D) HBr, hydrolysis followed by oxidation by K2C2O7.
CH3
NaOH P
70. H2 O
(Major Product)
Consider the above reaction. The number of  electrons present in the product ‘P ‘_______ is
71. The product formed in the following reaction. [JEE-Mains (25-Jun-Shift-1)2022]

CH3
CH3 H
C CH2 + H C CH3 ?
is
CH3
CH3
CH3
CH3 CH3 CH3
C CH2 CH2 CH C CH2 C CH3
(A) CH3 (B) CH
CH3 3
CH3 CH3
CH3 CH3
CH3
CH 3 CH CH CH CH3 C C CH3
CH3
(C) (D)
CH3 CH3 CH3 CH3
72. Amongst the following, the major product of the given chemical reaction is
Br2
Major Product
CH3OH [JEE-Mains (25-Jun-Shift-2)2022]
O
Br Br OCH3 OCH3
(A) (B) (C) (D)

O OCH3 O OCH3 O Br O Br
h
73. (C7H5O2 )2  [X]  2C6 H5  2CO2 [JEE-Mains (26-Jun-Shift-1)2022]
Consider the above reaction and identify the intermidiate ‘ X ‘
O O O O
 
(A) C6H5 C (B) C6H5 C O (C) C 6H 5 C O (D) C 6H 5 C O
 
74. The major product in the following reaction [JEE-Mains (26-Jun-Shift-2)2022]
(i) Hg(OAc) 2 ,H2O

?
(ii) NaBH 4
OH
(A) (B) (C) (D)
OH O OH
75. ‘P’ prime and ‘Q’ respectively are: [JEE-Mains (27-Jun-Shift-1)2022]
(1)O3
(P) 
(2)Zn H2 O
 Ethane- 1,2 -dicarbaldehyde + Glyoxal/Oxaldehyde
(1)O3
(Q) 
(2)Zn H2 O
 5-oxohexanal
(A) 1-methylcyclohex-1,3-diene & cyclopentene.
(B) Cyclohex-1,3-diene & cyclopentene
(C) 1-methylcyclohex-1,4-diene & 1-methylcyclopent-1-ene
(D) Cyclohex-1,3-diene & 1-methylcyclopent-1-ene
76. The major product (P) in the reaction [JEE-Mains (28-Jun-Shift-1)2022]

HBr
Ph Br ?(P) [Ph is -C 6H5]
Br
Br
Ph Br Ph Br
Ph Br
(A) (B) Ph (C) (D)
Br Br Br
Br
77. The major product (P) of the given reaction is [JEE-Mains (28-Jun-Shift-2)2022]
(where, Me is -CH3)
Me OH
+
H
P
Me Major product
Me
Me
Me Me Me Me Me Me
(A) Me (B) (C) (D)

Me Me CH2
Me
78. The major product of the following reaction contains ______bromine atom(s).
CH2
H3C
Br2 [JEE-Mains (28-Jun-Shift-2)2022]

Major Product
h
O
79. Two isomers ‘A’ and ‘B’ with molecular formula C4H8 give different products on oxidation with KMnO4
in acidic medium. Isomer ‘A on reaction with KMnO4 /H+ results in effervescence of a gas and gives
ketone. The compound ‘ A ‘ is [JEE-Mains (29-Jun-Shift-1)2022]
(A) But-1-ene. (B) cis-But-2-ene. (C) trans-But-2-ene. (D) 2-methyl propene.
80. A compound ‘A’ on reaction with ‘X’ and ‘Y’ produces the same major product but different by product
‘a’ and ‘b’. Oxidation of ‘a’ gives a substance produced by ants.
CH3 CH3
X
a + O =C CH2 C CH3
CH3 CH3
CH3
H2C C CH2 C CH3
CH3 CH3
CH3
Y b+O=C CH2 C CH3
Compound 'A'
CH3
‘X’ and ‘Y’ respectively are

(A) KMnO4/H+ and dil. KMnO4, 273 K (B) KMnO4(dilute), 273 K and KMnO4/H+
(C) KMnO4/H+ and O3, H2O/Zn (D) O3, H2O/Zn and KMnO4/H+
81. Major product of the following reaction is [JEE-Mains (25-July_Shift-2)2022]

O
2 HBr
Br Br Br
O Br O
(A) (B)
O O
Br
Br O Br
Br O
(C) (D)
O
O
82. The total number of monobromo derivatives formed by the alkanes with molecular formula C5H12 is
(excluding stereo isomers)___________. [JEE-Mains (25-July_Shift-2)2022]
83. The dark purple colour of KMnO4 disappears in the titration with oxalic acid in acidic medium. The
overall change in the oxidation number of manganese in the reaction is :
(A) 5 (B) 1 (C) 7 (D) 2

84. Cl + CH4 A+B [JEE-Mains (26-July_Shift-1)2022]
A and B in the above atmospheric reaction step are :
 
(A) C2H6 and Cl2 (B) CHCl and H2 (C) CH and HCl (D) C2H6 and HCl
2 3
85. The major product of the following reaction is [JEE-Mains (26-July_Shift-1)2022]
OCH3
O 2N
(i) Na/liq. NH 3
(ii) CH3CH2OH
OCH3 OCH3 OH OCH3

H
H H
O 2N
(A) O2N (B) H2N (C) (D) O2N
86. Total number of isomers (including stereoisomers) obtained on monochlorination of methylcyclohexane

is ________. [JEE-Mains (26-July_Shift-2)2022]
87. In the titration of KMnO4 and oxalic acid in acidic medium, the change in oxidation number of carbon
at the end point is ________ [JEE-Mains (27-July_Shift-1)2022]
88. Choose the correct option for the following reactions. [JEE-Mains (28-July_Shift-1)2022]
CH3
(BH3)2 Hg(OAc)2, H 2O
B H3C C CH CH2 A
H2O2/OH NaBH4
CH3
(A) ‘A‘ and ‘B‘ are both Markovnikov addition products.

(B) ‘A‘ is Markovnikov product and ‘B‘ is anti-Markovnikov product.
(C) ‘A‘ and ‘B‘ are both anti-Markovnikov products.
(D) ‘B‘ is Markovnikov and ‘A‘ is anti-Markovnikov product.
89. Identify the correct statement for the below given transformation. [JEE-Mains (28-July_Shift-1)2022]
C2H5ONa
H3C CH2 CH2 CH CH3 A + B
C2H5OH
 (Major) (Minor)
N(CH3)3
(A) A-CH3CH2CH=CH3, B-CH3CH2CH=CH2, Saytzeff products
(B) A-CH3CH2CH=CH–CH3, B-CH3CH2CH=CH2, Hofmann products
(C) A-CH3CH2CH2CH=CH2, B-CH3CH2CH=CHCH3, Hofmann products
(D) A-CH3CH2CH2CH=CH2, B-CH3CH2CH=CHCH3, Saytzeff products
OH
(1) I 2/NaHCO3
90. A [JEE-Mains (28-July_Shift-2)2022]
(2) Pyridine, 
O
Find out the major product for the above reaction

I
CO2 H
(A) O (B) (C) O (D) O
CH3 O O
91. Which among the following pairs of the structures will give different products on ozonolysis? (Consider
the double bonds in the structures are rigid and not delocalized.) [JEE-Mains (29-July_Shift-1)2022]
CH3 CH3
CH3 CH3
(A) (B)
CH3 CH3
CH3 CH3
CH3 CH3 CH3 CH3
CH3 CH3
(C) (D)
92. In bromination of Propyne, with Bromine 1, 1, 2, 2-tetrabromopropane is obtained in 27% yield. The amount
of 1,1,2, 2-tetrabromopropane obtained from 1g of Bromine in this reaction is ×10–1 g. (Nearest integer)
(Molar Mass : Bromine = 80 g/mol) [JEE-Mains (29-July_Shift-1)2022]
93. When enthanol is heated with conc. H2SO4, a gas is produced. The compound formed, when this gas is
treated with cold dilute aqueous solution of Baeyer’s Question: reagent, is
(A) formaldehyde (B) formic acid (C) glycol (D) ethanoic acid
Environmental chemistry
94. Some gases are responsible for heating of atmosphere (green house effect). Identify from the following
the gaseous species which does not cause it. [JEE-Mains (24-Jun-Shift-2)2022]
(A) CH4 (B) O3 (C) H2O (D) N2
95. Given below are two statements: one is labelled as Assertion A and the other is labelled as Reason R
Assertion A: Polluted water may have a value of BOD of the order of 17 ppm.
Reason R : BOD is a measure of oxygen required to oxidise both the biodegradable and
nonbiodegradable organic material in water.
below. [JEE-Mains (25-Jun-Shift-2)2022]
(B) Both A and R are correct but R is NOT the correct explanation of A.
(C) A is correct but R is not correct.
(D) A is not correct but R is correct.
96. Polar stratospheric clouds facilitate the formation of : [JEE-Mains (26-Jun-Shift-1)2022]

(A) ClONO2 (B) HOCl (C) ClO (D) CH4
97. Sulphur dioxide is one of the components of polluted air. SO2 is also a major contributor to acid rain.
The correct and complete reaction to represent acid rain caused by SO2 is :
(A) 2SO2 + O2  2SO3 (B) SO2 + O3  SO3 + O2
(C) SO2 + H2O2  H2SO4 (D) 2SO2 + O2 + 2H2O  2H2SO4
98. Given below are two statements: [JEE-Mains (27-Jun-Shift-1)2022]
Statement I: Classical smog occurs in cool humid climate. It is a reducing mixture of smoke, fog and
sulphur dioxide
Statement II: Photochemical smog has components, ozone, nitric oxide, acrolein, formaldehyde, PAN
etc.
In the light of above statements, choose the most appropriate answer from the options give below
(A) Both Statement I and Statement II are correct
(B) Both Statement I and Statement II are incorrect
(C) Statement I is correct but statement II is incorrect
(D) Statement I is incorrect but Statement II is correct
99. The acid that is believed to be mainly responsible for the damage of TajMahal is
(A) Sulfuric acid (B) Hydrofluoric acid
(C) Phosphoric acid (D) Hydrochloric acid
100. Match List I with List II [JEE-Mains (26-July_Shift-2)2022]

List I (Pollutant) List II (Source)
(A) Microorganisms (I) Strip mining
(B) Plant nutrients (II) Domestic sewage
(C) Toxic heavy metals (III) Chemical fertilizer
(D) Sediment (IV) Chemical factory
(A) A-II, B-III, C-IV, D-I (B) A-II, B-I, C-IV, D-III
(C) A-I, B-IV, C-II, D-III (D) A-I, B-IV, C-III, D-II
Ans. A
(A) Microorganisms (I) Domestic sewage
(B) Plant nutrients (II) Chemical fertilizer
(C) Toxic heavy metals (III) Chemical factory
(D) Sediment (IV) Strip mining
101. Match List-I with List-II [JEE-Mains (27-July_Shift-1)2022]

List I List II
Pollutant Disease/sickness
(A) Sulphat (>500 ppm) (I) Methemoglobinemia
(B) Nitrate (>50 ppm) (II) Brown mottling of teeth
(C) Lead (> 50ppb) (III) Laxative effect
(D) Fluoride (>2ppm) (IV) Kidney damage
Choose the correct answer from the options given below :
(A) A-IV, B-I, C-II, D-III (B) A-III, B-I, C-IV, D-II
(C) A-II, B-IV, C-I, D-III (D) A-II, B-IV, C-III, D-I
102. Given below are two statements : [JEE-Mains (28-July_Shift-1)2022]

Statement I : In polluted water values of both dissolved oxygen and BOD are very low.
Statement II : Eutrophication results in decrease in the amount of dissolved oxygen. In the light of the above
statements, choose the most appropriate answer from the options given below :
(A) Both Statement I and Statement II are true
(B) Both Statement I and Statement II are false
(C) Statement I is true but Statement II is false
(D) Statement I is false but Statement II is true
Qualitative and Quantitative
103. Number of grams of bromine that will completely react with 5.0 g of pent-1-ene is_____10–2g. (Atomic
mass of Br=80 g/ mol ) (Nearest Integer) [JEE-Mains (25-Jun-Shift-1)2022]
104. Given below are two statements : [JEE-Mains (26-Jun-Shift-1)2022]

Statement I : In ‘Lassaigne’s Test’, when both nitrogen and sulphur are present in an organic compound,
sodium thiocyanate is formed.
Statement II : If both nitrogen and sulphur are present in an organic compound, then the excess of
sodium used in sodium fusion will decompose the sodium thiocyanate formed to giveNaCN and Na2 S.
In the light of the above statements, choose the most appropriate answer from the options Question:
given below :
105. Which of the following is structure of a separating funnel? [JEE-Mains (27-Jun-Shift-1)2022]
(A) (B) (C) (D)
106. 0.25 g of an organic compound containing chlorine gave 0.40 g of silver chloride in Carius estimation.
The percentage of chlorine present in the compound is ______. [in nearest integer]
(Given: Molar mass of Ag is 108 g mol–1 and that of Cl is 35.5 g mol–1)
107. Which one of the following techniques is not used to spot components of a mixture separated on thin
layer chromatographic plate? [JEE-Mains (28-Jun-Shift-1)2022]
(A) I2 (Solid)
(B) U.V. Light
(C) Visualisation agent as a component of mobile phase
(D) Spraying of an appropriate reagent
108. Which technique among the following, is most appropriate in separation of a mixture of 100 mg of p-
nitrophenol and picric acid ? [JEE-Mains (26-July_Shift-1)2022]
(A) Steam distillation (B) 2-5 ft long column of silica get
(C) Sublimation (D) Preparative TLC (Thin layer chromatography)
109. In Carius method of estimation of halogen, 0.45 g of an organic compound gave 0.36 g of AgBr. Find out the
percentage of bromine in the compound. [JEE-Mains (27-July_Shift-1)2022]
–1 –1
(Molar masses : AgBr = 188 g mol ; Br = 80g mol )
(A) 34.04 % (B) 40.04% (C) 36.03% (D) 38.04%
List-I (Mixture) List-II (Purification process)
(A) Chloroform & Aniline (I) Steam distillation
(B) Benzoic acid & Napthalene (II) Sublimation
(C) Water & Aniline (III) Distillation
(D) Napthalene & Sodium chloride (IV) Crystallisation
(A) A-IV ; B-III, C-I, D-II (B) A-III,B-I,C-IV, D-II
(C) A-III, B-IV, C-II, D-I (D) A-III, B-IV, C-I, D-II
111. Given below are two statements: One is labelled as Assertion A and the other is labelled as Reason R
Assertion A : Thin layer chromatography is an adsorption chromatography.
Reason R : A thin layer of silica gel is spread over a glass plate of suitable size in thin layer chromatography
which acts as an adsorbent.
In the light of the above statements, choose the correct answer from the options given below
(A) Both A and R are true and R is the correct explanation of A
(B) Both A and R are true but R is NOT the correct explanation of A
(C) A is true but R is false
(D) A is false but R is true
1. 1–bromo–3–chlorocyclobutane when treated with two equivalents of Na, in the presence of ether which of the
following will be formed ? [IIT ‘2005]
(A) (B) (C) (D)
2. Cyclohexene is best prepared from cyclohexanol by which of the following [IIT ‘2005]
(A) conc. H3PO4 (B) conc. HCl/ZnCl2 (C) conc. HCl (D) Conc. HBr
 (i) O
H ,
3.   X   3   Y.
(ii) Zn / CH COOH3
Identify X and Y. [IIT 2005]
4. CH3–CH=CH2 + NOCl  P Identify the adduct. [IIT 2006]
NO
|
(A) CH3  CH  CH2 (B) CH3  CH  CH2 (C) CH3  CH2  CH (D) CH2  CH2  CH2
| | | | | | |
Cl NO NO Cl Cl NO Cl
CH3
Cl2, hv
H3C fractional distillation
5. N(isothermeric products) C 5H 11Cl M(isomeric
CH3
products). What are N and M ? [IIT ‘2006]
(A) 6, 6 (B) 6, 4 (C) 4, 4 (D) 3, 3
6. The number of structural isomers for C6H14 is [IIT 2007]

(A) 3 (B) 4 (C) 5 (D) 6
7. The number of stereoisomers obtained by bromination of trans-2-butene is [IIT 2007]

(A) 1 (B) 2 (C) 3 (D) 4
8. The reagent(s) for the following conversion, [IIT 2007]

?

 H H
is / are
(A) alcoholic KOH (B) alcoholic KOH followed by NaNH2
(C) aqueous KOH followed by NaNH2 (D) Zn / CH3OH
9. The correct stability order for the following species is [IIT ‘2008]
O O
(I) (II) (III) (IV)
10. In the following carbocation, H/ CH3 that is most likely to migrate to the positively charged carbon is
[IIT 2009]
H H
1 2 + 4 5
H3C—C—C—C—CH3
3
HO H CH3
11. Intermediate produced when propene react with HCl in presence of peroxide [IIT 2009]
(A) CH 3 — CH 2 — CH2 (B) CH 3 — CH — CH 3
(C) CH 3 — CH2CH2 (D) CH 3 — CH — CH 3
12. The total number of cyclic isomers possible for a hydrocarbon with the molecular formula C4H6 is [IIT 2010]
13. The synthesis of 3 - octyne is achieved by adding a bromoalkane into a mixture of sodium amide and an alkyne.
The bromoalkane and alkyne respectively are [IIT 2010]
(A) BrCH2CH2CH2CH2CH3 and CH3CH2C  CH
(B) BrCH2CH2CH3 and CH3CH2C  CH
(C) BrCH2CH2CH2CH2CH3 and CH3C  CH
(D) BrCH2CH2CH2CH3 and CH3CH2C  CH
PASSAGE BASED PROBLEMS

PASSAGE 1
An acyclic hydrocarbon P, having moelcular formula C6H10, gave acetone as the only organic product through the
following sequence of reactions, in which Q is a intermediate organic compound.
[IIT 2011]
(i) dil. H2SO4/HgSO4
P
(ii) NaBH4/ehtanol
(C6H10)
(iii) dil. acid
O
(i) dil.H 2SO4/(catalytic)
amount) (–H2O) C
Q 2
(ii) O3/ethanol H 3C CH 3
(iii) Zn/H2O
14. The structure of the compound Q is

OH OH
H3C H3C
H C C CH2CH3 H3C C C CH3

(A) (B)
H3C H H3C H
H3 C OH OH
H C CH2CH CH3
(C) (D) CH3CH 2CH2CHCH2CH 3
H 3C
15. The structure of compound P is
(A) CH3CH2CH2CH2 – c  c – H (B) H3CH2C – C  C – CH2CH3
H3C H3C
H C C C CH 3 H3c C C C H
(C) (D)
H3C H3C
16. The maximum number of isomers (including stereoisomers) that are possible on mono - chlorination of the
following compound, is CH3 CH2 CH(CH3)CH2CH3 [IIT 2011]
17. The total number alkenes possible by dehydrobromination of 3-bromo-3-cyclopentylhexane using alcoholic KOH is
. [IIT 2011]
18. In Allene (C3H4), the type (s) of hybridisation of the carbon atoms is (are) [JEE Adv. 2012]
19. The number of optically active product obtained from the complete ozonolysis of the given compound is
CH3 CH3
CH3 CH CH C CH CH C CH CH CH3
[JEE Adv. 2012]
H CH3
(A) 0 (B) 1 (C) 2 (D) 4
Paragraph For Questions 22 and 23
Schemes 1 and 2 describe sequential transformation of alkynes M and N. Consider only the major products
formed in each step for both the schemes.
20. The product X is [JEE Adv. 2014]
(A) (B)
(C) (D)
21. The correct statement with respect to product Y is [JEE Adv. 2014]
(A) It gives a positive Tollens test and is a functional isomer of X.
(B) It gives a positive Tollens test and is a geometrical isomer of X.
(C) It gives a positive iodoform test and is a functional isomer of X.
(D) It gives a positive iodoform test and is a geometrical isomer of X.
22. Compound(s) that on hydrogenation produce(s) optically inactive compound(s) is(are) [JEE Adv. 2015]
(A) (B)
(C) (D)
23. In the following reaction, the major product is : [JEE Adv. 2015]
(A) (B)
(C) (D)
24. In the following reactions, the product S is [JEE Adv. 2015]

H3C
i. O3
R NH3
ii. Zn, H2O S
H3C H3C N
N
(A) (B)
N
N
(C) (D)
HC
3
HC
3
25. Which of the following reactions produce(s) propane as a major product ? [JEE Adv. 2019]
Br
(A) H3C electrolysis Zn
COONa + H2O (B) Br
H3C
Zn, dil. HCl
(C) H C Cl (D) H3C
3
COONa
26. In the reaction scheme shown below, Q, R and S are the major products. [JEE Adv. 2020]
The correct structure of
(A) S is (B) Q is
(C) R is (D) S is
27. The number of isomeric tetraenes (NOT containing sp-hybridized carbon atoms) that can be formed
from the following reaction sequence is ________. [JEE Advance 2022]
1. Na, liquid NH 3
2. Br 2 (excess)
3. alc. KOH
28. The number of –CH2– (methylene) groups in the product formed from the following reaction sequence
is ________. [JEE Advance 2022]
1. O3, Zn/H 2O
2. KMnO 4
3. NaOH, electrolysis
4. Cr 2O3, 770 K, 20 atm
1. A 2. A 3. D 4. A 5. C 6. C 7. A
8. A 9. A 10. D 11. D 12. A 13. A 14. D
15. C 16. C 17. C 18. A 19. D 20. C 21. C
22. A 23. B 24. C 25. A 26. A 27. A 28. C
29. D 30. D 31. C 32. A 33. D 34. A 35. A
36. D 37. A 38. D 39. C 40. C 41. A 42. 8
43. A 44. C 45. A 46. A 47. C 48. C 49. C
50. A 51. D 52. D 53. B 54. A 55. C 56. C
57. C 58. A 59. B 60. B 61. D 62. B 63. A
64. A 65. B 66. D 67. C 68. A 69. C 70. 2

71. B 72. A 73. D 74. A 75. D 76. C 77. C
78. 1 79. D 80. C 81. D 82. 8 83. A 84. C
85. A 86. 12 87. 1 88. B 89. C 90. C 91. C
92. 3 93. C 94. D 95. C 96. B 97. D 98. A
99. A 100. A 101. B 102. D 103. 1136 104. A 105. A
106. 40 107. C 108. D 109. A 110. D 111. A
O
1. D 2. A 3. (x) = , (Y) = CH 3 – C – (CH2) 4 – CH = O
CH3
4. A 5. B 6. C 7. A 8. B 9. D 10. D
11. B 12. 5 13. D 14. B 15. D 16. 8 17. 5
18. B 19. A 20. A 21. C 22. BD 23. D 24. A
25. CD 26. BD 27. 2 28. 0

Alkyl Halide | JEE Main
1. The correct order of the thermal stability of hydrogen halides (H – X) is – [AIEEE-2005]
(A) HF > HCl > HBr > HI (B) HI > HBr > HCl > HF
(C) HI > HCl < HF > HBr (D)HCl < HBr > HBr < HI
2. Tertiary alkyl halides are practically inert to substitution by SN2 mechanism because of – [AIEEE-2005]
(A) instability (B) insolubility (C) steric hindrance (D) inductive effect
3. Alkyl halides react with dialkyl copper reagents to give [AIEEE-2005]

(A) alkyl copper halides (B) alkenes
(C) alkenyl halides (D) alkanes
4. Elimination of bromine from 2–bromobutane results in the formation of – [AIEEE-2005]

(A) predominantly 2–butene (B) equimolar mixture of 1 and 2–butene
(C) predominantly 2–butyne (D) predominantly 1–butene
5. Among the following the one that gives positive iodoform upon reaction with I2 and NaOH is –[AIEEE 2006]
(A) C6H5 CH2CH2OH (B)

(C) PhCHOHCH3 (D) CH3 CH2CH(OH)CH2CH3
6. Which of the following is the correct order of decreasing SN2 reactivity ? [AIEEE 2007]
(A) RCH2X > R3CX > R2CHX (B) RCH2X > R2CHX > R3CX
(C) R3CX > R2CHX > RCH2X (D) R2CHX > R3CX > RCH2X
(X = a halogen)
7. The organic chloro compound, which shows complete stereochemical inversion during a SN2 reaction , is
[AIEEE 2008]
(A) (CH3)3CCl (B) (CH3)2CHCl (C) CH3Cl (D) (C2H5)2CHCl
8. Which of the following on heating with aqueous KOH, produces acetaldehyde ? [AIEEE 2009]
(A) CH3COCl (B CH3CH2Cl (C) CH2Cl CH2Cl (D) CH3CHCl2
9. Consider the following bromides : [AIEEE 2010]

Me
Me
Me
(i) Me (ii) (iii)
Br
Br Br
The correct order of SN1 reactivity is
(A) (ii) > (iii) > (i) (B) (ii) > (i) > (iii) (C) (iii) > (ii) > (i) (D) (i) > (ii) > (iii)
10. Which branched chain isomer of the hydrocarbon with molecular mass 72u gives only one isomer of mono
substituted alkyl halide ? [JEE Main 2012]
(A) Isohexane (B) Neohexane
(C) Tertiary butyl chloride. (D) Neopentane
11. Iodoform can be prepared from all except : [JEE Main 2012]
(A) 3 - Methyl - 2 - butanone (B) Isobutyl alcohol
(C) Ethyl methyl ketone (D) Isopropyl alcohol
12. What is DDT among the following [JEE Main 2012]

(A) Biodegradable pollutant (B) Non-biodegradable possutant
(C) Greenhouse gas (D) A fertilizer
13. Compound (A), C8H9Br, gives a white precipitate when warmed with alcoholic AgNO3. Oxidation of (A) gives
an acid (B), C8H6O4. (B) easily forms anhydride on heating. identify the compound (A). [JEE Main 2013]
CH2Br
CH2Br
CH2Br C2H5
(A) (B) (c) (D)

CH3 CH3 Br
CH3
14. A solution of (–) –1–chloro–1-phenylethane in toluene racemizes slowly in the presence of a small amount of
SbCl5. due to formation of : [JEE Main 2013]
(A) carbocation (B) free radical (C) carbanion (D) carbene
15. In SN2 reactions, the correct order of reactivity for the following compounds ? [JEE Main 2014]
CH3Cl, CH3CH2Cl, (CH3)2CHCl and (CH3)3CCl is
(A) CH3CH2Cl > CH3Cl > (CH3)2CHCl > (CH3)3CCl
(B) (CH3)2CHCl > CH3CH2Cl > CH3Cl > (CH3)3CCl
(C) CH3Cl > (CH3)2CHCl > CH3CH2Cl > (CH3)3CCl
(D) CH3Cl> CH3CH2Cl > (CH3)2CHCl > (CH3)3CCl
16. The synthesis of alkyl fluorides is best accomplished by : [JEE Main 2015]
(A) Free radical fluorination (B) Sandmeyer's reaction
(C) Finkelstein reaction (D) Swarts reaction
17. The major product obtained in the following reaction is : [JEE Main 2017]
Br
H
tBuOK
C6H5
C6H5 (+)
(A) C6H5CH = CHC6H5 (B) (+)C6H5CH(OtBu) CH2C6H5
(C) (–)C6H5CH(OtBu)CH 2C6H5 (D) (±)C6H5CH(OtBu)CH 2C6H5
18. The increasing order of the reactivity of the following halides for the SN1 reaction is : [JEE Main 2017]
CH3CHCH2CH3 CH3CH2CH2Cl p-H3CO–C6H4–CH 2Cl
Cl
(I) (II) (III)
(A) (II) < (I) < (III) (B) (I) < (III) < (II)
(C) (II) < (III) < (I) (D) (III) < (II) < (I)
19. Which of the following, upon treatment with tert-BuONa followed by addition of bromine water, fails to decolourize
the colour of bromine ? [JEE Main 2017]
O
C6H 5 O O
(A) (B) (C) (D)
Br Br Br Br
20. The major product formed in the following reaction is: [JEE Main 2018]
I OH I OH
(A) (B) (C) (D)
OH OH I I
21. The major product of the following reaction is : [JEE-Mains-2018]
Br NaOMe
MeOH
OMe OMe
(A) (B) (C) (D)
22. The major product of the following reaction is : [JEE-Mains Online -2019]
(i) KOH (alc.)

(2) Free radical
Cl Cl polymerisation
CH3 CH3
n n
n
n
(A) (B) (C) (D)

Cl
OH
OH Cl
23. Increasing order of reactivity of the following compunds for SN1 substitution is : [JEE-Mains Online -2019]
CH3
CH2 – Cl Cl Cl
H3C Cl
CH3
H3CO
(i) (ii) (iii) (iv)
(A) (ii) < (i) < (iv) < (iii) (B) (ii) < (iii) < (i) < (iv)
(C) (i) < (ii) < (iv) < (iii) (D) (ii) < (iii) < (iv) < (i)
24. Heating of 2-chloro-1 phenylbutane with EtOK/EtOH gives X as the major product. Reaction of X with Hg
(OAc)2/H2O followed by NaBH4 gives Y as the major product . Y is : [JEE-Mains Online -2019]
OH OH
(A) Ph (B) Ph (C) Ph (D) Ph

OH
Br
KOH alc (excess)

Ph
Br
(A) (B) (C) (D)

Ph Ph
Ph Ph
26. Which of the following compounds will show retention in configuration on nucleophile substitution by ion ?
[JEE-Mains Online -2020]
(A) (B) (C) (D)
27. The major aromatic product C in the following reaction sequence will be :
[JEE-Mains Online -2020]
(A) (B) (C) (D)
28. The major product obtained from E2-elimination of 3-bromo-2- fluoropentane is [JEE-Mains Online -2020]
CH3 CH3
| |
(A) CH3—CHz—C——CH—CH3 — CH3
(B) CH3CH2—CH—CH—
CH3
|
(C) CH 3—CH —
— CH—CH—CH 3 (D) CH3CH2CH —
—C—F
|
CH3
29. The mechanism of SN1 reaction is given as: [JEE-Mains Online -2020]
R—X R  X R|| X Y R — Y + X
Ion pair Solvent
Separated ion
pair
A student writes general characteristics based on the given mechanism as :

(a) The reaction is favoured by weak nucleophiles.
(b) R would be easily formed if the substituents are bulky
(c) The reaction is accompanied by racemization
(d) The reaction is favoured by non-polar solvents.
Which observations are correct ?
(A) (b) and (d) (B) (a) and (c) (C) (a) and (b) (D) (a), (b) and (c)
30. The decreasing order of reactivity of the following compounds towards nucleophilic substitution (S N2)
is : [JEE-Mains Online -2020]
(A) (II) > (III) > (I) > (IV) (B) (II) > (III) > (IV) > (I)
(C) (III) > (II) > (IV) > (I) (D) (IV) > (II) > (III) >(I)
31. When neopentyl alcohol is heated with an acid, it slowly converted into an 85 : 15 mixture of alkenes A and B,
respectively. What are these alkenes ? [JEE-Mains Online -2020]
(A) (B)
(C) (D)
32. Consider the reaction sequence given below : [JEE-Mains Online -2020]
Which of the following statements is true:

(A) Changing the concentration of base will have no effect on reaction (A)
(B) Doubling the concentration of base will double the rate of both the reactions
(C) Changing the concentration of base will have no effect on reaction (B)
(D) OH will have no effect on reaction (B)
33. The major product [B] in the following reaction is : [JEE-Mains Online -2020]
(A) CH2 = CH2 (B)
(C) (D) CH3 – CH2CH = CH – CH3
34. The major product [R] in the following sequence of reaction is : [JEE-Mains Online -2020]
H3C
H3C
(A) C = CH– CH3 (B) CH – CH= CH2
(CH3)2CH (CH3)2CH
H2C H3C
(C) C – CH2– CH3 (D) C = C(CH3)2
CH(CH3)2 H3CCH2
35. The major product in the following reaction is : [JEE-Mains Online -2020]
CH3CH = CHCH(CH3)2 HBr

(A) CH3CH(Br)CH 2CH(CH3) 2 (B) Br(CH 2) 3CH(CH 3) 2
(C) CH3CH2CH2C(Br)(CH 3) 2 (D) CH3CH2CH(Br)CH(CH 3) 2
OH CH2CH3
H2SO4
CHCH3 CH2CH3 CH2CH 3 CH = CH2
(A) (B) (C) (D)

O O O O
37. The major products of the following reaction are : [JEE-Mains Online -2020]
CH3 CH3
(A) + CH3CHO (B) + HCHO

H3C O H3C CHO
CH3 CH3
(C) + CH3COOH (D)

+ HCOOH
H3C H3C COOH
O
38. The major product in the following reaction is: [JEE-Mains Online -2020]
(A) (B) (C) (D)
39. The correct order of the following compounds showing increasing tendency towards nucleophilic substitution
reaction is : [JEE-Mains (24-Feb_Shift -2)2021]
Cl Cl Cl Cl
NO2 O2N NO2
NO2 NO2 NO2

(iii) (iv)
(i) (ii)
(A) (iv) < (i) < (iii) < (ii) (B) (iv) < (i) < (ii) < (iii)
(C) (i) < (ii) < (iii) < (iv) (D) (iv) < (iii) < (ii) < (i)
40. The total number of amines among the following which can be synthesized by Gabriel synthesis is _______.
CH 3 CH–CH 2–NH 2
(A) CH (B) CH3CH2NH2
3
CH2 –NH 2 NH2

(C) (D)
41. Identify A and B in the chemical reaction. [JEE-Mains (25-Feb_Shift -1)2021]
OCH 3
 A (Major)  
 B (Major)
NaI

HCl
dry acetone
NO2
OCH 3 I OCH 3 I
Cl Cl
A= B= A= B=
(A) (B)
Cl Cl
NO2 NO2 NO2 NO2
OCH 3 OCH 3 OCH 3 OCH3

Cl Cl I
A= B= A= B=
(C) (D)
Cl
NO2 NO2 NO2 NO2
42. Match List-I with List-II [JEE-Mains (26-Feb_Shift -2)2021]

List-I List-II
Cl
N2+ Cl–
(a)  
Cu2Cl2
 +N2 (i) Wurtz reaction
Cl
N2 +Cl–
(b)  
Cu,HCl
 +N2 (ii) Sandmeyer reaction
(c) 2CH3CH2Cl + 2Na  

Ether
 C2H5– C2H5 + 2NaCl (iii) Fitting reaction
(d) 2C2H5Cl +2Na  
Ether
 C6H5– C6H5 + 2NaCl (iv) Gatterman reaction
Choose the correct answer from the option given below:
(A) (a)-(ii), (b)-(i), (c)-(iv), (d)-(iii) (B) (a)-(iii), (b)-(iv), (c)-(i), (d)-(ii)
(C) (a)-(ii), (b)-(iv), (c)-(i), (d)-(iii) (D) (a)-(iii), (b)-(i), (c)-(iv), (d)-(ii)
43. Identify A in the given reaction [JEE-Mains (26-Feb_Shift -2)2021]
OH
SOCl 2
A (Major product)
HO CH2 OH
OH OH Cl
Cl
(A) (B) (C) (D)
OH CH2 Cl Cl CH2 Cl OH CH2 OH

Cl CH2 Cl
44. For the given reaction : [JEE-Mains (26-Feb_Shift -1)2021]
CH 2CH3
Br
 2
UV light
 'A'
(major product)
monobrominated
CN
What is ‘A’ ?
CH2 CH 3 Br CH3
CH2CH3 CH 2CH3 CH
Br
(A) (B) (C) (D)
CN
Br CN
Br CN CN
45. For the given reaction : [JEE-Mains (26-Feb_Shift -1)2021]
CH CHBr
1. NaNH
2.Red 2
 hot
      
iron tube, 873 K
(A)
(major product)
CH3
What is ‘A’
H3C CH 3
(A) CH = CH– NH2 (B) (C) (D) CH3CH2CH2NH2
CH3
CH3
46. Given below are two statements : [JEE-Mains (18-March_Shift -1)2021]
Statement I : C2H5OH and AgCN both can general nucleophile.
Statement II : KCN and AgCN both will generate nitrile nucleophile with all reaction condition.
Choose the most appropriate option:
(A) Statement I is false but statement II is true.
(B) Statement I is true but statement II is false.
(C) Both statement I and statement II are false.
(D) Both statement I and statement II are true.
H3C OH H3 C Cl
47. 20 % H3PO4 (CH3)3CO–K +
"A" "B"
358 K
(Major Product) (Major Product)
The products “A” and “B” formed in above reactions are: [JEE-Mains (16-March_Shift -1)2021]
CH3 CH2 CH 2 CH 3
(A) A– B– (B) A– B–
CH2 CH2 CH3 CH3
(C) A– B– (D) A– B–
Cl
A
48. [JEE-Mains (16-March_Shift -2)2021]
Cl
Identify the reagent(s) ‘A’ and condition(s) for the reaction

(A) A = HCl; Anhydrous AlCl3 (B) A = HCl, ZnCl2
(C) A = Cl2, dark, Anhydrous AlCl3 (D) A = Cl2; UV light
49. Ammonolysis of Alkylhalides followed by the treatment with NaOH solution can be used to prepare primary,
secondary and tertiary amines. The purpose of NaOH in the reaction is :
(A) to remove basic impurities [JEE-Mains (16-March_Shift -2)2021]
(B) to activate NH3used in the reaction
(C) to increase the reactivity of alkyl halide
(D) to remove acidic impurities
Cl O–Na+

+ NaOH
The above reaction requires which of the following reaction conditions?

(A) 623 K, 300 atm (B) 573 K, 300 atm
(C) 573 K, Cu, 300 atm (D) 623 K, Cu 300 atm
51. Which of the following reaction is an example of ammonolysis ?

(A) C6H5CH2CN  [ H]
 C6H5CH2CH2NH2 [JEE-Mains (17-March_Shift -1)2021]
(B) C6H5COCl + C6H5NH2 C6H5CONHC6H5
(C) C6H5CH2Cl + NH3 C6H5CH2NH2

(D) C6H5NH2 HCl
 C6 H 5 N H 3Cl –
52. The correct pair(s) of the ambident nucleophiles is (are) : [JEE-Mains (17-March_Shift -2)2021]
(A) AgCN/KCN
(B) RCOOAg/RCOOK
(C) AgNO2/KNO2
(D) AgI/KI
(A) (A) and (C) only (B) (B) only
(C) (B) and (C) only (D) (A) only
53. Match List-I with List-II : [JEE-Mains (18-March_Shift -1)2021]

List-I List-II
(Chemicals) (Use/Preparation/Constituent)
(a) Alcoholic potassium hydroxide (i) electrodes in batteries
(b) Pd/BaSo4 (ii) obtained by addition reaction
(c)BHC (Benzene hexachloride) (iii) used for -elimination reaction
(d) Polyacetylene (iv) Lindlar’s Catalyst
Choose the most appropriate match :
(A) (a)-(ii), (b)-(i), (c)-(iv), (d)-(iii) (B) (a)-(iii), (b)-(i), (c)-(iv), (d)-(ii)
(C) (a)-(ii), (b)-(iv), (c)-(i), (d)-(iii) (D) (a)-(iii), (b)-(iv), (c)-(ii), (d)-(i)
54. In the given reaction 3-Bromo-2,2-dimethyl butane [JEE-Mains (20-July_Shift -1)2021]

C2H5OH
‘A’
(Major product)
Product A is :
(A) 2-Hydroxy-3,3-dimethyl butane. (B) 2-Ethoxy-2,3-dimethyl butane.
(C) 2-Ethoxy-3,3-dimethyl butane. (D) 1-Ethoxy-3,3-dimethyl butane
55. In Carius method, halogen containing organic compound is heated with fuming nitric acid in the presence of :
(A) AgNO3 (B) HNO3 (C) BaSO4 (D)CuSO4
56. Given below are two statements, one is labeled as Assertion (A) and other is labeled as:-
Assertion (A): Gabriel phthalimide synthesis cannot be used to prepare aromatic primary amines.
Reason (R) :Aryl halides do not undergo nucleophilic substitution reaction.
In the light of the above statements, choose the correct answer form the options given below.
(A) (A) is true but (R) is flase
(B) (A) is false but (R) is true
(C) Both (A) and (R) are true but (R) is not the correct explanation of (A).
(D) Both (A) and (R) are true and (R) is correct explanation of (A).
57. What is A in the following reaction? [JEE-Mains (27-July_Shift-2)2021]
(A) (B)
(C) (D)
58. In the following sequence of reaction the P is : [JEE-Mains (27-August_Shift-1)2021]
Cl
dry ethanol P
+ Mg [A]
ether (Major Product)
O–CH2 CH 3
(A) (B)
CH2CH 3
(C) (D)
59. Given below are two statements: one is labelled as Assertion (A) and the other is labelled as
Reason (R). [JEE-Mains (27-August_Shift-1)2021]
Assertion (A). Synthesis of ethyl phenyl ether may be achieved by Williamson synthesis.
Reason (R): Reaction of bromobenzene with sodium ethoxide yields ethyl phenyl ether. In the light of the
above statements, choose the most appropriate answer from the options given below:
(A) Both (A) and (R) are correct and (R) is the correct explanation of (A)
(B) Both (A) and (R) are correct but (R) is NOT the correct explanation of (A)
(C) (A) is correct but (R) is not correct
(D) (A) is not correct but (R) is correct
60. The major product of the following reaction, if it occurs by SN2 mechanism is :
OH
K2CO3
+ Br acetone
O O
(A) (B)
O
(C) (D) O
61. The major product (A) formed in the reaction given below is :
CH 3–CH 2– CH–CH2 –Br
CH OH
+ CH3 O-   3
A [JEE-Mains (27-August_Shift-2)2021]
 Major product 
CH 3–CH 2– CH–CH2Br
CH3–CH2– CH–CH 2 –OH
(A) (B)
OCH3
CH 3–CH 2– CH–CH2–OCH3 CH3 –CH2 – C=CH2
(C) (D)
62. The correct of reactivity of the given chlorides with acetate in acetic acid is :
CH3
Cl Cl CH2Cl Cl CH3
> > >
(A)
CH3
CH3
Cl Cl CH2Cl
Cl CH3
> >
>
(B)
CH3
CH 3
Cl CH 2Cl Cl CH 3 Cl
> > >
(C)
CH 3
CH 3
CH2Cl Cl Cl Cl CH 3
> > >

(D)
CH 3
63. The major product of the following reaction is: [JEE-Mains (31-August_Shift-2)2021]
CH3
Cl
NaOH
Major Product
C 2H5 OH
CH 3
CH 3
CH3 CH 3
OH
(A) (B) (C) (D)
OH
HO
64. In the given reaction sequence, the major product: [JEE-Mains (24-Jun-Shift-1)2022]
HNO3 Br2 alcohlic
C8H10 
H SO
 A 
 B KOH
c
2 4
NO 2
(A) C CH2 (B) O 2N CH CH2
NO 2
O 2N C CH2
(C) (D) CH CH2
NO2
65. Arrange the following carbocations in decreasing order of stability.


O O

 [JEE-Mains (24-Jun-Shift-2)2022]
(A) (B) (C)
(A) A > C > B (B) A > B > C (C) C > B > A (D) C > A > B
66. The conversion of propan-1-ol to n-butylamine involves the sequential addition of reagents. The correct
sequential order of reagents is [JEE-Mains (24-Jun-Shift-2)2022]
(A) (i) SoCl2 (ii) KCN (iii) H2/Ni, Na(Hg)/C2H5OH
(B) (i) HCI (ii) H2/Ni.Na(Hg) /C2H5OH
(C) (i) SOCl2 (ii) KCN (iii) CH3NH2
(D) (i) HCl (ii) CH3NH2
67. Phenol on reaction with dilute nitric acid, gives two products. Which method will be most efficient for
large scale separation? [JEE-Mains (25-Jun-Shift-1)2022]
(A) Chromatographic separation (B) Fractional Crystallisation
(C) Steam distillation (D) Sublimation
68. The major product in the reaction [JEE-Mains (25-Jun-Shift-1)2022]

CH3 CH3
+ - ?
CH3 C Cl +K O C CH3
CH3 CH3
(A) t-Butyl ethyl ether (B)2,2-Dimethyl butane

(C) 2-Methyl pent-1-ene (D) D 2-Methyl prop-1-ene
69. The correct order of nucleophilicity is [JEE-Mains (26-Jun-Shift-2)2022]

 
(A) F  OH (B) H2 O  OH (C) ROH  RO

(D) NH2  NH3
 
70. Oxidation of toluene to Benzaldehyde can be easily carried out with which of the following reagents?
(A) CrO3/acetic acid, H3O+ (B) CrO3 acetic anhydride, H3O+
(C) KMnO4 /HCl, H3O+ (D) CO/HCl, anhydrous AlCl3
71. The major product of the following reaction is : [JEE-Mains (27-Jun-Shift-1)2022]
CH3
F

PhS Na
DMF
NO2
SPh I SPh SPh
F SPh F SPh
(A) (B) (C) (D)
NO 2 NO 2 NO2 NO2
72. What will be the major product of following sequence of reactions?

(i) n-BuLi
n-C5H11Cl
n Bu [JEE-Mains (27-Jun-Shift-2)2022]
(ii) Lindlar cat, H 2
n-Bu n-Bu
(A) (B)
H 11C 5 n-Bu n-Bu C 5H11
C 5H 11
H11C5 n-Bu
(C) (D)
n-Bu
73. Product ‘A’ of following sequence of reactions is [JEE-Mains (27-Jun-Shift-2)2022]

(a)Br2 ,Fe
Ethylbenzene 
(b)Cl , 
 'A'
2 Majorproduct
(c)alc.KOH
Cl Br Cl
C CH2 C CH2 CH CH2
(A) (B) (C) (D)
Br Br
74. Which one of the following compounds is inactive towards SN1reaction?
CH3
C Cl Cl
(A) CH3 (B)
CH3
CH3
C Cl
(C) (D) H
Cl

Statement I : Phenols are weakly acidic.
Statement II : Therefore they are freely soluble in NaOH solution and are weaker acids than alcohols
and water.
Choose the most appropriate option :
76. Most stable product of the following reaction is : [JEE-Mains (25-July_Shift-1)2022]
OH
(i) H3C SO2Cl, Pyridine
(ii) NaCN, DMF
CN CN CN CN
(A) (B) (C) (D)
77. An organic compound ‘A‘ contains nitrogen and chlorine. It dissolves readily in water to give a solution
that turns litmus red. Titration of compound ‘A’ with standard base indicates that the molecular weight
of ‘A‘ is 131±2. When a sample of ‘A‘ is treated with aq. NaOH, a liquid separates which contains N but
not Cl. Treatment of the obtained liquid with nitrous acid followed by phenol gives orange precipitate.
The compound ‘A’ is: [JEE-Mains (27-July_Shift-2)2022]
+ -
+ -
NH2 + - NH3Cl
NH3Cl CH2NH3 Cl
Cl
(A) (B) (C) (D)
78. Given below are two statements : one is labelled as Assertion A and the other is labelled as Reason R
Assertion A : Aniline on nitration yields ortho, meta & para nitro derivatives of aniline.
Reason R: Nitrating mixture is a strong acidic mixture.
In the light of the above statements, choose the correct answer from the options given below
(C) A is true but R is false
(D) A is talse but R is true
CH3
Cl
NH3 Br2
79. 'A' (C8H 6Cl2O) C 8H8 CINO
NaOH
H2N
Consider the above reaction, the compound ‘A’ is
O O
O O
Cl Cl H
Cl Cl
(A) (B) (C) (D)
Cl Cl
Cl CH3 H3C
CH3 CH2Cl
-
N NCl
NaOH
+ 'A' Product
80. (Orange-red dye)
Which among the following represent reagent ‘A’ ?
OH NH2 NH2
OH
(A) (B) (C) (D)
81. Consider the following reaction sequence : [JEE-Mains (29-July_Shift-1)2022]

NH2
(i) AlH (i-Bu) 2 CH3CHO

'A' B
(ii) H 2O dill NaOH, 
(Major prodcut)
CN
The product ‘B’ is
(A)OHC N CH CH3 (B) H2N CH CH CHO
(C) H2N CH2 N CH CH3 (D) H2N C N CH CHO
82. The hinsberg reagent is [JEE-Mains (29-July_Shift-2)2022]

O
+ -
N2 Cl
S Cl
(A) O (B)
N N
- +
(C) NK (D)
HO
Haloalkane and haloarne

83. An organic compound ‘A’ on reaction with NH3 followed by heating gives compound B. Which on
further strong heating gives compound C(C8H5NO2). Compound C on sequential reaction with ethanolic
KOH, alkyl chloride and hydrolysis with alkali gives a primary amine. The compound A is :
CHO CHO COOH CHO
(A) (B) (C) (D)

CHO COOH COOH OH
84. In base vs. acid titration, at the end point methyl orange is present as
(A) quinonoid form (B) heterocyclic form (C) phenolic form (D) benzenoid form
85. The correct stability order of the following diazonium salt is [JEE-Mains (26-July_Shift-1)2022]
+ - + -
+ N Cl- N2 Cl + - N2 Cl
2 N 2 Cl
(A) (B) (C) (D)
OCH3 NO2 CN
(A) (A) > (B) > (C) > (D) (B) (A) > (C) > (D) > (B)
(C) (C) > (A) > (D) > (B) (D) (C) > (D) > (B) > (A)
86. The correct sequential order of the reagents for the given reaction is
NO2 OH
NH2 I
(A) HNO2, Fe/H+, HNO2, KI, H2O/H+ (B) HNO2, KI, Fe/H+, HNO2, H2O/warm
(C) HNO2, KI, HNO2, Fe/H+, H2O/H+ (D) HNO2, Fe/H+, KI, HNO2, H2O/warm
87. In the following reaction [JEE-Mains (27-July_Shift-1)2022]

SO3H OH
Oleum NaOH (excess)

+
H
(I) (II)
The % yield for reaction I is 60% and that of reaction II is 50%. The overall yield of the complete
reaction is ____ %. [nearest integer]

List-I List-II
COCl CHO
(A) H2 (I) Gatterman Koch reaction

Pd-BaSO4
SnCl2 /HCl
H3C CN H3C CHO
(B) + (II) Etard reaction
H 3O
CH3 CHO
(C) CrO 2Cl2 (III) Stephen reaction

+
H3 O
CHO
(D) CO, HCl (IV) Rosenmund reaction

AlCl 3 (anhyd)

(A) A-IV, B-III, C-II, D-I (B) A-I, B-II, C-III, D-IV
(C) A-II, B-III,C-IV, D-I (D) A-III,B-II, C-I, D-IV
CH3 CHO
89. [JEE-Mains (27-July_Shift-2)2022]
5g (92%)
In the above reaction, 5g of toluene is converted into benzaldehyde with 92% yield. The amount
of benzaldehyde produced is _________ × 10–2g. (Nearest integer)
90. Identify the major products A and B for the below given reaction sequence.
Cl
(1) CH3CHCH3, AlCl3

(2) O2 Na2Cr2O7/H2SO4
 P A
(3) H, H2O
Br2 in CS2
OH OH O OH
(A) and (B) and
Br O Br
O OH OH OH
Br Br Br Br
(C) and (D) and
O Br Br
91. Arrange the following in increasing order of reactivity towards nitration

A. p-xylene B. bromobenzene C. mesitylene D. nitrobenzene E. benzene
Choose the correct answer from the options given below : [JEE-Mains (28-July_Shift-2)2022]
(A) C < D < E < A < B (B) D < B < E < A < C (C) D < C < E < A < B (D) C < D < E < B < A
92. Compound I is heated with Conc. HI to give a hydroxy compound A which is further heated with Zn dust
to give compound B. Identify A and B.
O
Conc. HI Zn, 
A B [JEE-Mains (28-July_Shift-2)2022]

I
O
OH
OH
(A) A = ;B= (B) A = ;B=
O
OH
OH
(C) A = ;B= (D) A = ;B=
OH
Br2 NH2OH P2 O 5
A B C

CHO
Consider the above reaction sequence, the product ‘C’ is

OH
OH
Br Br Br Br
Br Br
Br Br
(A) (B) (C) (D)
CN CHO
CHO
CN
1. The following compound on hydrolysis in aqueous acetone will give : [IIT 2005]
CH 3 CH3 CH 3
CH 3 CH3 CH 3
NO 2
(K) NO 2 (L)
H Cl CH 3
H OH CH 3
CH 3 CH3 CH 3 CH 3 CH3 CH 3
NO 2 (M) NO 2
OH H CH 3 H CH3 OH
(A) mixture of (K) and (L) (B) mixture of (K) and (M)
(C) only (M) (D) Only (K)
2. Cyclohexene is best prepared from cyclohexanol by which of the following [IIT ‘2005]
(A) conc. H3PO4 (B) conc. HCl/ZnCl2 (C) conc. HCl
3. 1–bromo–3–chlorocyclobutane when treated with two equivalents of Na, in the presence of ether which of the
following will be formed? [IIT ‘2005]
(A) (B) (C) (D)
 (i) O
H ,
4.   X   3   Y. [IIT 2005]
(ii) Zn / CH3COOH
Identify X and Y.
5. Match the following : [IIT 2006]

Column I
(A) CH3—CHBr—CD3 on treatment with alc. KOH gives CH2 = CH — CD3 as a major product
(B) Ph—CHBr—CH3 reacts faster than Ph—CHBr—CD3.
(C) Ph—CH2—CH2Br on treatment with C2H5OD/C2H5O— gives Ph—CD = CH2 as the product.
(D) PhCH2CH2Br and PhCD2CH2Br react with same rate
Column II
(P) E1 reaction
KOH gives CH2 = CH — CD3 as a major product (Q) E2 reaction
(R) E1 cb reaction gives Ph—CD = CH2 as the product.
(S) First order reaction
6. The reagent(s) for the following conversion.

Br ?
H H is/are [IIT 2007]
Br
(A) alcoholic KOH
(B) alcoholic KOH followed by NaNH2
(C) aqueous KOH followed by NaNH2 (D) Zn/CH3OH
7. The number of stereoisomers obtained by bromination of trans-2-butene is [IIT 2007]

(A) 1 (B) 2 (C) 3 (D) 4
8. The major product of the following reaction is [IIT 2008]
Me Br
F
 
Ph S N a
    
dim ethyl formamide
NO2
Me SPh Me SPh Me Br Me SPh
F F SPh SPh
(A) (B) (C) (D)
NO2 NO2 NO2 NO2
9. The correct stability order for the following species is [IIT ‘2008]
O O
(I) (II) (III) (IV)
10. In the following carbocation, H/CH3 that is most likely to migrate positively charged carbon is [IIT 2009]
H H
1 2 + 4 5
H3C – C – C – C – CH3
HO H CH3
11. The synthesis of 3-octyne is achieved by adding a bromoalkane into a mixture of sodium amide and an alkyne.
The bromoalkane and alkyne respectively are – [IIT 2010]
(A) BrCH 2CH2CH2CH2CH3 and CH3CH2CCH
(B) BrCH2CH2CH3 and CH3CH2CH2CCH
(C) BrCH2CH2CH2CH2CH3 and CH3CCH
(D) BrCH2CH2CH2CH3 and CH3CH2CCH
12. The bond energy (in kcal mol–1) of a C – C single bond is approximately [IIT 2010]
(A) 1 (B) 10 (C) 100 (D) 1000
13. The major product

O of the following reaction is : [IIT 2011]
C
(i) KOH
NH
C
(ii) Br CH 2Cl
O
O O
C C
(A) N—CH2 Br (B) N CH 2Cl
C C
O O
O O
C C
(C) N (D) N
C C
O — CH2 Br O CH2Cl
14. The total number of alkenes possible by dehydrobromination of 3-bromo-3-cyclopentylhexane using alcoholic
KOH is : [IIT 2011]
RCH2OH
+
H (anhydrous)
O
(A) a hemiacetal (B) an acetal (C) an ether (D) an ester
16. KI in acetone, undergoes SN2 reaction with each of P,Q,R and S. The rates of the reaction vary as.
O
H3C—Cl Cl
Cl
[JEE Adv. 2013]
(A) P>Q>R>S (B) S>P>R>Q (C) P>R>Q>S (D) R>P>S>Q
17. The reactivity of compound Z with different halogens under appropriate conditions is given below :
mono halo substituted derivative when X2 = l2

OH
X2
di halo substituted derivative when X2 = Br2
C(CH3)3 [JEE Adv. 2014]
Z
Tri halo substituted derivative when X2 = Cl 2
The observed pattern of electrophilic substitution can be explaind by :

(A) the steric effect of the halogen
(B) the steric effect of the tert-butyl group
(C) the electronic effect of the phenolic group
(D) the electronic effect of the tert-butyl group
18. In the following monobromination reaction, the number of possible chiral products is: [JEE Adv. 2016]
CH2CH2CH3
Br2(1.0 mole)
H Br
CH3 300°C
(1.0 mole)
(enantiomerically pure)
19. For the following compounds, the correct statement(s) with respect to nucleophilic substitution reactions is (are)
[JEE Adv. 2017]
CH 3 CH3
Br Br H 3C—C—Br Br
CH 3
(I) (II) (III) (IV)
(A) I and II follow SN2 mechanism
(B) Compound IV undergoes iniversion of configuration
(C) The order of reactivity for I, III and IV is : IV > I > III
(D) I and III follows SN1 mechanism
20. In the following reaction sequence, the correct structure(s) of X is (are) [JEE Adv. 2018]
Me N3
(1) PBr3, Et2O
X
(2) NaI, Me2CO
(3) NaN3, HCONMe2
enantiomerically pure
Me OH Me OH
(A) (B) (C) (D)
Me OH Me OH
21. LIST-I contains reactions and LIST-II contains major products. [JEE Adv. 2018]
LIST-I LIST-II
P. + 1.
ONa Br OH
Q. + HBr 2.
OMe Br
R. + NaOMe 3.
Br OMe
S. + MeBr 4.
ONa
O
5.
Match each reaction in LIST-I with one or more product in LIST-Il and choose the correct option.
(A) P  1, 5; Q  2; R  3; S  4 (B) P  1, 4; Q  2; R  4; S  3
(C) P  1, 4; Q  1, 2; R  3, 4; S  4 (D) P  4, 5; Q  4; R  4; S  3, 4
22. Choose the correct option(s) for the following set of reactions [JEE Adv. 2019]
(i) MeMgBr conc. HCl S

C6H 10O Q
(ii) H 2o (major)
20% H3PO4, 360 K
(i) H2, Ni HBr, benzoyl peroxide

T R U
(major) (ii) Br2, hv (major)
(major)
H3C Cl CH3 CH3 H3C Br

Br Br
(A) (B)
S U U T
CH3 H3C Br H3C Br CH3

Cl Cl
(C) (D)
S T U S
23. Which of the following plots is(are) correct for the given reaction ? [JEE Advance 2020]
([P]0 is the initial concentration of P)
+ NaOH + NaBr
P Q
(A) (B) (C) (D)

1. A 2. C 3. D 4. A 5. C 6. B 7. C
8. D 9. A 10. D 11. B 12. B 13. B 14. A
15. D 16. D 17. A 18. A 19. D 20. A 21. C
22. D 23. A 24. A 25. D 26. A 27. A 28. D
29. D 30. B 31. B 32. A 33. B 34. D 35. C
36. B 37. D 38. A 39. C 40. C 41. D 42. C
43. B 44. D 45. C 46. B 47. A 48. D 49. D
50. A 51. C 52. A 53. D 54. B 55. A 56. D
57. B 58. B 59. C 60. B 61. D 62. B 63. C
64. B 65. A 66. A 67. C 68. D 69. D 70. B
71. A 72. C 73. D 74. C 75. C 76. B 77. D
78. A 79. C 80. A 81. B 82. A 83. C 84. A
85. B 86. B 87. 30 88. A 89. 530 90. B 91. B
92. D 93. D
1. A 2. A 3.
O
4. (x) (y)
CH3–C–(CH2)4–CHO
CH3
5. AQ ; BQ ; CR,S, ; DR,S,
6. B 7. A 8. A 9. D 10. D 11. D 12. C
13. A 14. 5 15. B 16. B 17. ABC 18. 5 19. A, D

20. B 21. B 22. A,B 23. A
Aromatic Compound | JEE Main
1. p–cresol reacts with chloroform in alkaline medium to give the compound A which adds hydrogen cyanide to
form, the compound. B The latter on acidic hydrolysis gives chiral carboxylic acid. The structure of the carboxylic
acid is - [AIEEE-2005]
CH3 CH3 CH3 CH3
CH(OH)COOH CH2COOH CH2COOH
(A) CH(OH)COOH (B) (C) (D)

OH OH OH OH
OH O–Na+
2. + CHCl3 + NaOH  .
CHO
The electrophile involved in the above reaction is : [AIEEE 2006]

(A) dichlorocarbene (:CCl2) (B) trichloromethyl anion ( C Cl3 )
 
(C) formyl cation ( C HO ) (D) dichloromethyl cation ( C HCl 2 )
3. The structure of the compound that gives a tribromo derivative on treatment with bromine water is -
[AIEEE 2006]
CH3
CH3 CH3
CH2OH OH
(A) (B) (C) (D)
OH OH
4. Fluorobenzene (C6H5F) can be synthesized in the laboratory - [AIEEE 2006]

(A) from aniline by diazotisation followed by heating the diazonium salt with HBF4
(B) by direct fluorination of benzene with F2 gas
(C) by reacting bromobenzene with NaF solution
(D) by heating phenol with HF and KF
5. Phenyl magnesium bromide reacts with methanol to give - [AIEEE 2006]

(A) a mixture of benzene and Mg(OMe) Br
(B) a mixture of toluene and Mg(OH)Br
(C) a mixture of phenol and Mg(Me)Br
(D) a mixture of anisole and Mg(OH) Br
6. The reaction of toluene with Cl2 in presence of FeCl3 gives predominantly - [AIEEE 2007]
(A) benzoyl chloride (B) benzyl chloride (C) o-and p-chlorotoluene (D) m-chlorotoluene
7. The compound formed as a result of oxidation of ethyl benzene by KMnO4 is – [AIEEE-2007]

(A) benzophenone (B) acetophenone (C) benzoic acid (D) benzyl alcohol
8. The electrophile, E attacks the benzene ring to generate the intermediate -complex. Of the following, which
-complex is of lowest energy ? [AIEEE 2008]
NO
NO
NO
H H
+
(A) + E (B) E (C) + H (D)
+
E H E
9. Toluene is nitrated and the resulting product is reduced with tin and hydrochloric acid. The product so obtained is
diazotised and then heated with cuprous bromide. The reaction mixture so formed contains - [AIEEE 2008]
(A) mixture of o– and p-dibromobenzenes (B) mixture of o- and p-bromoanilines
(C) mixture of o- and m-bromotoluenes (D) mixture of o- and p-bromotoluenes
10. Phenol, when it first reacts with concentrated sulphuric acid and then with concentrated nitric acid, gives -
[AIEEE 2008]
(A) o-nitrophenol (B) p-nitrophenol (C) nitrobenzene (D) 2, 4, 6-trinitrobenzene
11. In the chemical reactions. [AIEEE-2010]

NH2
NaNO2 HBF4
(A) (B)
HCl, 278K
The compounds ‘A’ and ‘B’ respectively are

(A) nitrobenzene and chlorobenzene (B) nitrobenzene and flurobenzene
(C) phenol and benzene (D) benzene diazonium chloride and flurobenzene
12. In the chemical reactions [AIEEE-2011]
NH2
NaNO2 CuCN B,
A
HCl,278 K 
the compounds A and B respectively are :

(A) Benzene diazonium chloride and benzonitrile (B) Nitrobenzene and chlorobenzene
(C) Phenol and bromobenzene (D) Fluorobenzene and phenol
13. Sodium phenoxide when heated with CO2 under pressure at 125º C yields a product which on acetylation produces
C? [JEE Main 2014]
ONa
+
125º H
+ CO2 B C
5 Atm Ac2O
The major product C would be;
OH OCOCH3 OCOCH3 OH
COOCH3 COOH
COCH3
(A) (B) (C) (D)
COOH
COCH3
14. For which of the following molecule significant  0 ? [JEE Main 2014]
Cl CN OH SH
(a) (b) (c) (d)
Cl CN OH SH
(A) Only (c) (B) (c) and (d) (C) Only (a) (D) (a) and (b)
15. In the reaction [JEE Main 2015]
NH2
NaNO2/HCl
D
0 - 5°C
CuCN/KCN
CH3
E + N2
the product E is:
CN CH3 COOH
(A) (B) (C) (D) H3C CH 3
CH3 CH3
16. In the following sequence of reactions:

KMnO4 SOCl2
Toluene A B
H2/Pd BaSO4
C
the product C is: [JEE Main 2015]
(A) C6H5CH2OH (B) C6H5CHO (C) C6H5COOH (D) C6H5CH3
17. Which of the following compounds will form significant amount of meta product during mono-nitration reaction ?
[JEE Main 2017]
(A) (B) (C) (D)
18. The major product of the following reaction is : [JEE Main _ 2-Sept-2020 _Shift-2]
OH
CH3
Conc. HNO3 + Conc. H2SO4
NO2
OH
OH OH OH
CH3
CH3 NO2 CH3 NO2 CH3
(A) (B) (C) NO2 (D)
NO2 NO2 O2 N NO2
NO2
19. Three isomers A, B and C (molecular formula C8H11N) give the following results :
[JEE Main _ 3-Sept-2020 _Shift-2]
R has lower boiling point than S

C H SO Cl
6 5 2
B   alkali-insoluble product A, B and C respectively are :
(A)
(B)
(C)
(D)
20. [P] on treatment with Br2/FeBr3 in CCl4 produced a single isomer C8H7O2Br wile heating [P] with sodalime gas
toluene. The compound [P] is : [JEE Main _ 4-Sept-2020 _Shift-1]
(A) (B) (C) (D)
21. In the following reaction sequence, [C] is : [JEE Main _ 4-Sept-2020 _Shift-2]
(A) (B)
(C) (D)
22. The final major product of the following reaction is : [JEE Main _ 5-Sept-2020 _Shift-2]
Me
(i) Ac2O/ Pyridine
(ii) Br2 , FeCI3
(iii) OH- / 
NH2
Br
Me Me Br Me
Me
(A) (B) Br (C) (D) Br

NH2 NH2 NH2
NH2
23. The increasing order of boiling points of the following compounds is : [JEE Main _ 5-Sept-2020 _Shift-2]
OH OH OH OH
CH3 NO2 NH2 OCH3

I II III IV
(A) I < IV < III < II (B) IV < I < II < III (C) I < III < IV < II (D) III < I < II < IV
24. The IUPAC name of the following compound is : [JEE Main _ 6-Sept-2020 _Shift-2]
(A) 2-nitro-4-hydroxymethyl-5 amino benzaldehyde

(B) 3-amino-4-hydroxymethyl-5-nitrogenzaldehyde
(C) 4-amino-2-formyl-5-hydroxymethyl nitrogenzene
(D) 5-amino-4-hydroxymethyl-2-nitrobenzaldehyde
25. The correct match between Item – I (starting material) and Item-II (reagent) for the preparation of
benzaldehyde is: [JEE Main _ 6-Sept-2020 _Shift-2]
Item-I Item-II
(I) Benzene (P) HCl and SnCl2, H3O+
(II) Benzonitrile (Q) H2, Pd-BaSO4,S and quinoline
(III) Benzoyl Chloride (R) Co, HCl and AlCl3
(A) (I)-(R), (II)-(Q) and (III)-(P) (B) (I)-(Q), (II)-(R) and (III)-(P)
(C) (I)-(P), (II)-(Q) and (III)-(R) (D) (I)-(R), (II)-(P) and (III)-(Q)
26. A solution of phenol in chloroform when treated with aqueous NaOH gives compound P as a major product. The
mass percentage of carbon in P is_______. (to the nearest integer) [JEE Main _ 6-Sept-2020 _Shift-2]
(Atomic mass : C = 12; H = 1; O = 16)
27. The correct order of the following compounds showing increasing tendency towards nucleophilic substitution
reaction is : [JEE Main _ 24-Feb-2021 _Shift-2]
Cl Cl Cl Cl
NO2 O2N NO2
NO2 NO2 NO2

(iii) (iv)
(i) (ii)
(A) (iv) < (i) < (iii) < (ii) (B) (iv) < (i) < (ii) < (iii)
(C) (i) < (ii) < (iii) < (iv) (D) (iv) < (iii) < (ii) < (i)
28. The diazonium salt of which of the following compounds will form a coloured dye on reaction with -Naphthol in
NaOH ? [JEE Main _ 24-Feb-2021 _Shift-2]
CH 3
NH–CH 3 CH2NH 2 NH2 N CH3

(A) (B) (C) (D)
29. What is the correct sequence of reagents used for converting nitrobenzene into m-dibromobenzene ?
NO2 Br
[JEE Main _ 24-Feb-2021 _Shift-2]

Br
(A) 
Sn/HCl Br
 /  NaNO
 / 
2 NaBr
 /   2

(B) 
Sn/HCl KBr
 /  Br
/  H
 /  2

(C) 
NaNO HCl
 / 
2 KBr
 /  H
/ 
(D) 
Br /Fe Sn/HCl
 / 
2 NaNO /HCl
 /  CuBr /HBr
/  2

30. In the following reaction the reason why meta–nitro product also formed is:
NH2 NH2 NH2

NH2
NO2
Conc. HNO3
+ +
Conc. H2SO4, 288K
NO2
NO2
[A] [B] [C]
51% 47% 2%
(A) Formation of anilinium ion [JEE Main _ 24-Feb-2021 _Shift-1]

(B) –NO2 substitution always takes place at meta–position
(C) low temperature
(D) –NH2 group is highly meta–directive
31. ‘A’ and ‘B’ in the following reactions are : [JEE Main _ 24-Feb-2021 _Shift-1]
NH 2
NaNO2 /HCl SnCl2 /HCl/H3 O+

(A) (B)
KCN
+
CN Cl N2Cl– Cl
(A) (A) : (B) : (B) (A) : (B) :
CN CHO N2 Cl– CHO
(C) (A) : (B) : (D) (A) : (B) :
32. Which of the following compound gives pink colour on reaction with phthalic anhydride in conc.H2SO4 followed
by treatment with NaOH ? [JEE Main _ 24-Feb-2021 _Shift-1]
H 3C CH3 CH 3
(A) (B)
HO OH OH
HO CH CH
(C) (D)
CH HO
HO
33. The major product of the following reaction is : [JEE Main _ 25-Feb-2021 _Shift-2]
NO2
H 2 SO4
NO2 NO2 NO2

NO2
(A) (B) (C) (D)
NH 2 NH 2 NH 2 NH2
NO2
HNO3 ,H2SO4
  + +
34.
288 K NO2
NO2
(A) (B) (C)
(A) Reaction is possible and compound (A) will be major product. [JEE Main _ 25-Feb-2021 _Shift-2]
(B) The reaction will form sulphonated product instead of nitration.
(C) group is ortho and para directive, so product (B) is not possible.
(D) Reaction is possible and compound (B) will be the major product.
35. Identify A in the given chemical reaction. [JEE Main _ 25-Feb-2021 _Shift-1]
CH3
CH 2
Mo2O3
CH 3 'A'
CH 2 773 K, 10-20 atm
CH major product
CH 2 CH 3
CH3 CH3
(A) (B) (C) (D)
36. Which of the following reaction/s will not give p-aminoazobenzene? [JEE Main _ 25-Feb-2021 _Shift-1]
NO2
i) Sn/HCl
(A) ii) HNO2
iii) Aniline
NO2
i) NaBH 4
B) ii) NaOH
iii) Aniline
NH 2
i) HNO2
(C) ii) Aniline, HCl
(A) B only (B) A and B (C) C only (D) A only

37. Consider the following chemical reaction. [JEE Main _ 25-Feb-2021 _Shift-1]
HC CH   Product

(1)Red hot Fe tube, 873K
(2) COHCl/AlCl3
The number of sp2 hybridized carbon atom(s) present in the product is _______.
38. Match List-I with List-II [JEE Main _ 26-Feb-2021 _Shift-2]

List-I List-II
Cl
N2+ Cl–
(a)  
Cu2Cl2
 +N2 (i) Wurtz reaction
Cl
N2 +Cl–
(b)  
Cu,HCl
 +N2 (ii) Sandmeyer reaction
(c) 2CH3CH2Cl + 2Na  

Ether
 C2H5– C2H5 + 2NaCl (iii) Fitting reaction
(d) 2C2H5Cl +2Na  
Ether
 C6H5– C6H5 + 2NaCl (iv) Gatterman reaction
Choose the correct answer from the option given below:
(A) (a)-(ii), (b)-(i), (c)-(iv), (d)-(iii)
(B) (a)-(iii), (b)-(iv), (c)-(i), (d)-(ii)
(C) (a)-(ii), (b)-(iv), (c)-(i), (d)-(iii)
(D) (a)-(iii), (b)-(i), (c)-(iv), (d)-(ii)
39. Identify the major products A and B respectively in the following reaction of phenol :
[JEE Main _ 26-Feb-2021 _Shift-1]
OH
(i) CHCl 3, NaOH Br2 in CS 2
B A
(ii) H 3O + 273K
OH OH
CHO OH OH
and Br CHO
(A) (B) and
Br
OH OH OH OH
Br
and and
(C) (D)
CHO Br CHO
O
NH2 KOBr A
(major product)
Br
O
40.
NH2 LiAlH 4 B [JEE-Mains (20-July_Shift-2)2021]
+
H3 O (major product)
Br
In the above reactions, product A and product B respectively are :

NH2 NH2
(A) NH2 (B) NH 2
,
Br , Br
Br
NH 2 NH2
NH2 NH 2
(C) (D)
Br ,
41. Benzene on nitration gives nitrobenzene in presence of HNO3 and H2SO4 mixture, where :
(A) HNO3 acts as an acid and H2SO4 acts as a base [JEE-Mains (20-July_Shift-2)2021]
(B) both H2SO4 and HNO3 act as a bases
(C) HNO3 acts as a base and H2SO4 acts as an acid
(D)both H2SO4 and HNO3 act as an acids
42. (i) (C6H5 CO) 2O2, HBr P
(ii) CoF2 (major product)

Br
Major product P of above reaction, is : [JEE-Mains (20-July_Shift-2)2021]
(A) F (B)
Br F
B
F
(C) (D) F
Br F
43.
Consider the above reaction, compound B is : [JEE-Mains (20-July_Shift-2)2021]

(A)
(B)
(C)
(D)
44. Which one of the following reactions does not occur ? [JEE-Mains (22-July_Shift-2)2021]
NH 2 NH 2
(A) + AlCl3 + CH 3Cl 
CH 3
NH2 NH2
(B)
+ H 2SO4 
SO3H
NH2 NHCOCH 3
(C)
+ (CH3CO) 2O/Pyridine 
NH2 NH2
(D) + HNO3/H2SO4 
NO2
N2+Cl–
CH2 CH3
B, Anhyd. Al Cl3
45. +A + H 2O
Major Product
In the chemical reaction given above A and B respectively are : [JEE-Mains (22-July_Shift-2)2021]
(A) CH3CH2OH and H3PO2 (B) H3PO2 and CH3CH2Cl
(C) H3PO2 and CH3CH2OH (D) CH3CH2Cl and H3PO2
46. An organic compound A (C6H6O) gives dark green colouration with ferric chloride. On treatment with CHCl3
and KOH, followed by acidification gives compound B. Compound B can also be obtained from compound C
on reaction with pyridinium chlorochromate (PCC). Identify A, B and C. [JEE-Mains (22-July_Shift-2)2021]
OH CH 2OH OH
OH CH O
(A) A = B= C=
HO CH2OH OH
CHO OH
(B) A = B= C =
CH2OH OH OH
OH CHO
(C) A = B= C =
OH OH
OH CHO CH2 OH
(D) A = B= C=
47. The given reaction can occur in the presence of: [JEE-Mains (25-July_Shift -1)2021]
OH OH
Br
(Major Product)
(A)Bromine water (B) Br2 in CS2, 273 K (C) Br2 FeBr3 (D) Br2 in CHCl3, 273 K
Choose the correct answer from the options given below:
(A) (a) and (c) only (B) (b), (c) and (d) only
(C) (a), (b) and (d) only (D) (b) and (d) only
P
 
 (Yellow coloured
Sn  HCl C6H5 N2 Cl
48. C6H5NO2  “A” 
H compund)
Consider the above reaction, the Product “P” is: [JEE-Mains (25-July_Shift-2)2021]
N=N NH 2 N=N
(A) (B)
NH 2
H H
N N =N–N
(C) (D)
49. The correct sequential addition of regents in the preparation of 3-nitrobenzoic acid from benzene is :
(A) Br2/AlBr3,NaCN, H3O+,HNO3/H2SO4 [JEE-Mains (26-August_Shift-1)2021]
(B) HNO3/H2SO4,Br2/AlBr3,Mg/ether,CO2, H3O+
(C) Br2/AlBr3,HNO3/H2SO4,Mg/ether,CO2, H3O+
(D) Br2/AlBr3,HNO3/H2SO4,NaCN,H3O+
50. The correct options for the products A and B of the following reactions are :
OH
Br 2(Excess) Br2
A B
H2O CS2, <5°C [JEE-Mains (26-August_Shift-1)2021]
OH OH OH OH
Br Br Br Br Br
A= , B= A= , B=
(A) Br
(B)
Br Br Br
OH OH OH OH
Br Br Br
A= , B= A= , B=
(C) (D)
Br Br Br Br
51. Consider the given reaction, the Product A is : [JEE-Mains (26-August_Shift-2)2021]
O Br
O
(A) (B)
Br
(C) (D)
Br
Br
52. Which one of the following phenols does not give colour when condensed with phthalic anhydride in presence
of conc. H2SO4? [JEE-Mains (26-August_Shift-2)2021]
OH
OH
OH
OH OH
(A) (B) (C) (D)
OH
CH3
53. The correct structures of A and B formed in the following reactions are :
OH O O
H 2 /Pd O
A B
C2 H 5 OH 1.0eq. (Major Product)
NO2
OH OH O OH O CH 3
CH 3
(A) (A) : (B) : (B) (A) : (B) :
NH2 NH2 NH2 NH 2

O O
O CH3 O CH 3
OH OH
(C) (A) : (B) : (D) (A) : (B) :
NH 2 NH CH 3
NH 2 NH CH3
O
O
54. The total number of regents from those given below, that can convert nitrobenzene into aniline is _________.
(Integer answer) [JEE-Mains (31-August_Shift-1)2021]
I. Sn – HCl II. Sn – NH4OH
III. Fe – HCl IV. Zn – HCl
V. H2 – Pd VI. H2 – Raney Nickel
55. Identify correct A, B and C in the reaction sequence given below: [JEE-Mains (31-August_Shift-2)2021]
conc. HNO3
+
conc. H 2SO4 Cl 2 Fe/HCl
A B C
 Anhyd. AlCl3
NO2 NO2 Cl Cl NH 2
(A) A = , B= , C =
NO2 NO2 Cl
A = , B= , C=
(B)
Cl OH
NO2 NO2 NH2
A = , B= , C=
(C)
Cl OH
NO2 NO2 NH2
A = , B= , C=
(D)
Cl Cl
56. The major products A and B formed in the following reaction sequence are:
NH 2
O O
O Br2, CH3COOH
A B [JEE-Mains (31-August_Shift-2)2021]
Room Temperature
NH2 NH 2
Br
A= , B=
(A)
COCH 3 COCH3
NH2 NH2
Br Br
A= , B=
(B)
COCH3 COCH3
O O
NH CH3 NH CH 3
(C)
A= , B =
Br
O O
NH CH3 NH CH3
(D) A= , B=
Br
57. For the following sequence of reactions, the correct products are:
1. B r2 /Fe/
2. Mg/dry ether
Products [JEE-Mains (31-August_Shift-2)2021]
3. CH 3OH
H OCH 3 OCH 3
+ Mg + HMgBr
(A) (B)
Br
Br H CH 3 OH
(C) + Mg (D) + Mg
OCH 3 Br
58. The structures of A and B formed in the following reaction are: [Ph = –C6H5]
O
+ O AlCl (2 eq)
Zn/Hg
3
 A 
 HCl
B [JEE-Mains (31-August_Shift-2)2021]
O
O
(A) A = Ph
Ph
,B=
OH
O OH
Ph OH
(B) A = , B = Ph
OH
O
Ph Ph
(C) A =
,B=
O
OH
Ph Ph
(D) A = ,B=
O
59. Identify A in the following reaction. [JEE-Mains (1-September_Shift-2)2021]
NH 2
K2Cr2O7
A
NH2
NO2 NO2
(A) (B) (C) H (D)

KO
60. The intermediate X , in the reaction : [JEE-Mains (25-Jun-Shift-1)2022]
OH OH
CHO
(1) NaOH
CHCl3+Aq. NaOH + [X] +
(2) H
- + - +
OH OH O Na O Na
CCl3 CHCl2 CHCl2 CCl3

(A) (B) (C) (D)
61. In the following reaction: [JEE-Mains (25-Jun-Shift-1)2022]

H3C CH3 H3C CH3
CH C O O H
+
H
+O 2 A and B
H 2O
The compounds A and B respectively are :

CH3 OH
(A) CH3COOH3 (B) , CH3COOH3

OH
OH OH
OH
(C) , CH3COOH3 (D) , CH3COOH3
62. Halogenation of which one of the following will yield m-substituted product with respect to methyl
group as a major product? [JEE-Mains (26-Jun-Shift-2)2022]
CH3 CH3 CH3 CH3
OH
(A) (B) (C) (D)
CHO NO2 NO2
63. Match List I with List II. [JEE-Mains (27-Jun-Shift-2)2022]
List I List II
OH OH
CHO
I Br 2 in CS 2
(A)
OH
II NaCr 2O 7/H2SO4
(B)
OH O
(C) III. Znl
OH OH
IV. CHCl 3 / NaOH

(D)
Br

(A) A-IV, B-III, C-II, D-I (B) A-IV, B-III, C-I, D-II
(C) A-II, B-III, C-I, D-IV (D) A-IV, B-II, C-III, D-I
64. Which of the following is most stable? [JEE-Mains (27-Jun-Shift-2)2022]

 
(A) (B) (C) (D)
(i) Cl 2,
A -
65. (ii) CN 4-Bromophenyl acetic acid. [JEE-Mains (28-Jun-Shift-2)2022]
+
(iii) H 2O/H
In the above reaction ‘ A’ prime is
Br Br
CH3 CH CH2
(A) (B) (C) (D)

Br Br
CH2CH3
66. With respect to the following reaction, consider the given statements:
NH2
HNO3
products
H2SO4,288 k [JEE-Mains (28-Jun-Shift-2)2022]
(A) o-Nitroaniline and p-nitroaniline are the predominant products.

(B) p-Nitroaniline and m-nitroaniline are the predominant products.
(C) HNO3 acts as an acid.
(D) H2SO4 acts as an acid.
Choose the correct option.
(A)A and C are correct statements. (B) A and D are correct statements.
(C) B and D are correct statements. (D) B and C are correct statements.
NH2
NH2
Br2(excess) (i) (CH 3 CO)2O

67. A B
H 2O Major Product (ii) Br, CH 3 COOH Major Product
(iii) HCl
Consider the above reactions, the product A and product B respectively are
NH2 NH2 NH2 NH2
Br Br Br Br
and and
(A) (B)
Br Br Br Br
NH2 NH2 NH2 NH2
Br Br Br Br
and and
(C) (D)
Br Br Br Br
Anhydrous,AlCl 3
+ CH3CH2CH2CI 'A'
68. [JEE-Mains (29-Jun-Shift-2)2022]
Major Product
The stable carbocation formed in the above reaction is


CHCH2CH3
  
(A) CH 3CH 2 CH 2 (B) CH3CH2 (C) CH 3 CH CH3 (D)
69. Two isomers (A) and (B) with Molar mass 184 g mol and elemental composition C, 52.2 % ; H, 4.9 %
and Br 42.9 % gave benzoic acid and p-bromobenzoic acid, respectively on oxidation with KMnO4.
Isomer ‘A’ is optically active and gives a pale yellow precipitate when warmed with alcoholic AgNO3.
Isomer ‘ A ‘ and ‘ B ‘ Question: are, respectively [JEE-Mains (29-Jun-Shift-2)2022]
CH2Br CH2CH3
CH2Br
CH3
CH3
and
(A)H3C CHBr C6H 5 and (B)
Br
CH2CH3 CH2CH3
H3C CHBr C6 H5 and and H3C CHBr C6 H 5

(C) (D)
Br Br
70. In Friedel-Crafts alkylation of aniline, one gets [JEE-Mains (29-Jun-Shift-2)2022]

(A) alkylated product with ortho and para substitution.
(B) secondary amine after acidic treatment.
(C) an amide product.
(D) positively charged nitrogen at benzene ring.
71. The reaction of R C NH2 with bromine and KOH gives RNH2 as the end product. Which one of the
O
following is the intermediate product formed in this reaction?
(A) R C NH Br (B) R NH Br (C)R N C O (D) R C NBr2
O O
72. Which statement is NOT correct for p-toluenesulphonyl chloride?

(A) It is known as Hinsberg’s reagent. + 4 marks
(B)It is used to distinguish primary and secondary amines.
(C)On treatment with secondary amine, it leads to a product, that is soluble in alkali.
(D) It doesn’t react with tertiary amines.
73. The final product ‘C ‘ in the following series of reactions [JEE-Mains (26-Jun-Shift-2)2022]
NO2
Sn/HCl NaNO2 Naphthol
A B C is
HCl NaOH
N N OH
(A) (B)
OH
N N Ph
N N OH
(C) (D) Ph N N
HO

Statement - I : In Hofmann degradation reaction, the migration of only an alkyl group takes place from
carbonyl carbon of the amide to the nitrogen atom.
Statement - II : The group is migrated in Hofmann degradation reaction to electron deficient atom.
below :
75. Identify the major product formed in the following sequence of reactions :
NH2
(1) Br2/H2O
(2) NaNO2/HCl
(3) H3PO2
NH . NH 2 OH
Br Br Br
Br Br
(A) (B) (C) (D)

Br
Br Br
76. A primary aliphatic amine on reaction with nitrous acid in cold (273 K) and there after raising temperature
of reaction mixture to room temperature (298 K), gives
(A) nitrile (B) alcohol (C) diazonium salt (D) secondary amine
77. The difference in the reaction of phenol with bromine in chloroform and bromine in water medium is
due to : [JEE-Mains (26-July_Shift-1)2022]
(A) Hyperconjugation in substrate (B) Polarity of solvent
(C) Free radical formation (D) Electromeric effect the substrate
78. Hydrolysis of which compound will give carbolic acid ? [JEE-Mains (26-July_Shift-2)2022]
(A) Cumene (B) Benzenediazonium chloride
(C) Benzal chloride (D) Ethylene glycol ketal
79. The number of non-ionisable protons present in the product B obtained from the following reaction is
__________. [JEE-Mains (26-July_Shift-2)2022]
C2H5OH + PCl3  C2H5Cl + A
A + PCl3 B
CH2 OH
 NaI
+ HCl A B
OH
In the above reaction product B is :

CH2 I CH2 I CH2Cl CH2Cl
(A) (B) (C) (D)
OH I OH I
81. The structure of A in the given reaction is : [JEE-Mains (27-July_Shift-2)2022]
O
NaOH
A
R major prodcut
Br
OH
OH
O O
R C CH3
R C CH3
(A) (B) (C) (D) OH
CH2CH3 R R
H3C Br
82. Major product B of the following reaction sequence is : [JEE-Mains (27-July_Shift-2)2022]

Br2 HI
H3C C CH CH3 A B
CH3OH
(major product)
CH3
OH Br I Br Br OH Br I
(A) H3C C CH CH3 (B) H3C C CH CH3 (C) H3C C CH CH3 (D) H3C C CH CH3
CH3 CH3 CH3 CH3
83. The major product in the given reaction is [JEE-Mains (28-July_Shift-2)2022]

+
OH (1) H , heat
(2) HBr
Br
Br Br
Br
(A) (B) (C) (D)
'A' AgCN
(Major product) NaCN
84. C2 H5OH H2O
Cl 'B'
C2H5OH H2 O (Major product)
Considering the above reaction, the compound ‘A’ and compound ‘B’ respectively are :
 
(A) N C , N C
(B) C N , C N
 
(C) N C , C N
(D) C N , N C
1. Which of the following is obtained when 4- Methylbenzenesulphonic acid is hydrolysed with excess of sodium
acetate ? [JEE 2005]
–+
(A) CH3 COONa (B) CH3 + SO3
–+
(C) CH3 SO3Na + CH3COOH (D) CH3 SO2O.COCH3 + NaOH
( i) O 2 / 
2. 3  P (
+ Cl – CH2CH2 – CH3 AlCl
  Q + Phenol P and Q are respectively [JEE 2006]
ii ) H 3O 
(A) + CH3CH2CHO (B) + CH3COCH3
(C) + CH3COCH3 (D) + CH3CH2CHO
Comprehension Type : (Q.3 to Q.5)

Reimer -Tiemann reaction introduces an aldehyde group on to the aromatic ring of phenol, ortho to the hydroxyl
group. This reaction involves electrophilic aromatic substitution. This is a general method for the synthesis of
substituted salicyladehydes as depicted below. [JEE 2007]
OH ONa OH
CHO CHO
I  (II)
(I)  aq
.HCl
 (III)
CH3 CH3 CH 3
3. Which one of the following reagents is used in the above reaction?

(A) aq NaOH + CH3Cl (B) aq NaOH + CH2Cl2
(C) aq NaOH + CHCl3 (D) aq NaOH + CCl4
4. The electrophile in this reaction is

(A) :CHCl (B) CHCl
+
2 (C) :CCl2 (D) CCl3
5. The structure of the intermediate I is
ONa ONa ONa ONa

CH 2Cl CHCl 2 CCl3 CH2OH
(A) (B) (C) (D)
CH3 CH3 CH3 CH3
6. In the following reaction [JEE-2007]
..
N con. HNO3
X
H con. H 2SO 4
the structure of the major product ‘X’ is
O2N
NO2
(A) N (B) N
H H
N O2N N
(C) H (D) H
NO2
7. Statement-1: p- Hydroxybenzoic acid has a lower boiling point than o- hydroxybenzoic acid. [JEE 2007]
Statement-2: o-Hydroxybenzoic acid has intramolecular hydrogen bonding.
(A) Statement-1 is True Statement-2 is True Statement-2 is a correct explanation for Statement-1
(B) Statement-1 is True Statement-2 is True Statement-2 is Not explanation for Statement-1
(C) Statement-1 is True Statement-2 is False
(D) Statement-1 is False Statement-2 is True
8. Statement-1: Bromobenzene upon reaction with Br2 / Fe gives 1,4-dibromobenzene as the major product.
Statement-2: in bromobenzene the inductive effect of the bromo group is more dominant than the mesomeric
effect in directing the incoming electrophile. [JEE 2008]
9. Statement-1 : Aniline on reaction with NaNO2 /HCl at 0°C followed by coupling with [JEE 2008]
 - naphthol gives a dark blue coloured precipitate. Statement-2 : The colour of the compound formed in the
reaction of aniline with NaNO2 / HCl at 0° followed by coupling with  naphthol is due to the extended conjugation.
10. The compounds P,Q and S [JEE 2010]
COOH OCH3
C
(P) (Q) (S)
HO H3C
were separately subjected to nitration using HNO3 / H2SO4 mixture.The major product formed in each case
respectively is
COOH OCH3
C
(A) HO H3C
NO2 NO2 O2N
OCH3
COOH
C
(B) H 3C
HO NO2
NO2 NO 2
COOH NO2
OCH3
C
(C) HO
H3C NO2
NO2
COOH
OCH3
C
(D) HO NO2
H3C NO2
NO2 O2N
OH
11. In the reaction NaOH

 ( aq ) / Br2
 the intermediate (s) is (are) [JEE 2010]
OO OO
O
OO
Br
(A) (B) (C) (D)
Br Br Br
Br Br
12. Amongst the compounds given the one the would form a brilliant colored dye on treatment with NaNO2 in dil. HCl
followed by addition to an alkaline solution of  - naphthol is [JEE 2011]
N(CH3)2 NHCH 3 NH 2 CH 2NH 2
(A) (B) (C) (D)

H3 C
Multiple Choice Question:
13. In the following reaction, the product(s) formed is (are) [JEE Adv. 2013]
OH
CHCl3
–
OH
CH3
O OH OH
OH
OHC CHO CHO
H3C CHCl2 H3C CHCl2 CH3

CH3
Q R S
P
(A) P(major) (B) Q(minor) (C) R(minor) (D) S(major)
14. For the identification of -naphthol using dye test, it is necessary to use [JEE Adv. 2014]
(A) dichloromethane solution of -napthol
(B) acidic solution of -naphthol
(C) neutral solution of -naphthol
(D) alkaline solution of -naphthol
15. Among
Cl P,Q,R and S, the aromatic compound(s) is/are [JEE Adv. 2014]
AlCl3
P
NaH
Q
(NH4)2CO3
R
100-115 ºC
O O
O
HCl S
(A) P (B) Q (C) R (D) S
PARAGRAPH
In the following reactions
Pd-BaSO 4 i. B2H6 2 HO i. EtMgBr, H2O
C8H6 C8H8 X 
HgSO ,H SO
 C8H8O Y
H2 ii. H 2O2 NaOH, H 2O 4 2 4 ii. H+, heat
16. Compound X is
O OH
OH
CH3 CH3 COH
(A) (B) (C) (D)
17. The major compound Y is [JEE Adv. 2015]

CH2 CH3
CH3
CH3 CH3 CH3
(A) (B) (C) (D)
18. Among the following, reaction(s) which gives(give) tert-butyl benzene as the major product is (are)
[JEE Adv. 2016]
Br
Cl
(A) (B)
NaOC 2H5 AlCl 3
OH
(C) H2SO4 (D) BF3OEt2
Paragraph-1
The reaction of compound P with CH3MgBr (excess) in (C2H5)2O followed by addition of H2O gives Q. The
compound Q on treatment with H2SO4 at 0°C gives R. The reaction of R with CH3COCl in the presence of
anhydrous AlCl3 in CH2Cl2 followed by treatment with H2O produces compound S. [Et in compound P is ethyl
group]
(H3C)3C
CO 2Et
Q R S
P
Q.19 The reaction, Q to R and R to S, are : [JEE Adv. 2017]
(A) Friedel-Crafts alkylation and Friedel-acylation
(B) Dehydration and Friedel-Crafts acylation
(C) Friedel-Crafts alkylation, dehydration and Friedel-Crafts acylation
(D) Aromatic sulfonation and Friedel-Crafts acylation
Q.20 The product S is : [JEE Adv. 2017]
COCH3 H3COC
(H3C)3C CH 3 (H3C)3C H3C CH 3
(A) (B)
H3C HO3S
CH 3 O
(H3C)3C (H3C) 3C CH 3
(C) (D)
COCH3 COCH3
21. In the following reaction sequence, the amount of D (in g) formed from 10 moles of acetophenone is_______.
(A tomic weight in g mol–1: H = 1, C = 12, N = 14, O = 16, Br = 80. The yield (%) corresponding to the product
in each step is given in the parenthesis) [JEE Adv. 2018]
O
NaOBr Br2/KOH Br2(3 equiv)

A B C D
H3O+ AcOH
(60%) (50%) (50%) (100%)
22. Choose the correct option(s) that give(s) an aromatic compound as the major product
[JEE Adv. 2019]
(i) alc. KOH
Br (ii) NaNH 2
NaOEt
H3C
(A) (B) Br (iii) red hot iron tube, 873 K
Br
NaOMe UV, 500 K

(C) (D) + Cl2 (excess)
23. In the following reaction, compound Q is obtained from compound P via an ionic intermediate.
[JEE(Advanced)-2020]
What is the degree of unsaturation of Q ?

24. Consider the reaction sequence from P to Q shown below. The overall yield of the major product Q from P is
75%. What is the amount in grams of Q obtained from 9.3 mL of P ? (Use density of P = 1.00 g mL–1 ; Molar
mass of C = 12.0, H= 1.0, O=16.0 and N = 14.0 g mol–1) [JEE-Advanced 2020]
25. An organic compound (C8H10O2) rotates plane-polarized light. It produces pink color with neutral FeCl3 solution.
What is the total number of all the possible isomers for this compound ? [JEE Advanced 2020]
26. Considering the following reaction sequence, the correct statement(s) is(are)
O
O O
Zn/Hg, HCl SOCl2

P Q R
AlCl3
AlCl3
a hydrocarbon Zn/Hg, HCl

S
(A) Compounds P and Q are carboxylic acids. [JEE Advance 2022]
(B) Compound S decolorizes bromine water.
(C) Compounds P and S react with hydroxylamine to give the corresponding oximes.
(D) Compound R reacts with dialkylcadmium to give the corresponding tertiary alcohol.
27. The weight percentage of hydrogen in Q, formed in the following reaction sequence, is ________.
Cl
1. NaOH, 623 K, 300 atm

Q (major product) [JEE Advance 2022]
2. conc. H 2SO 4 and then
conc. HNO 3
[Given: Atomic mass of H = 1, C = 12, N = 14, O = 16, S = 32, Cl = 35]
28. If the reaction sequence given below is carried out with 15 moles of acetylene, the amount of the
product D formed (in g) is ________. [JEE Advance 2022]
iron tube Cl 1. O 2
+
(red hot) H3C 2. H3O CH3COCl
HC CH A B C pyridine D
AlCl3
(80%) (50%) -CH3COCH3 (50%) (100%)
The yields of A, B, C and D are given in parentheses.

[Given: Atomic mass of H = 1, C = 12, O = 16, Cl = 35]
29. Considering the reaction sequence given below, the correct statement(s) is(are)
O

1. N K
COOH
1. Br 2, red phosphorous O
H3C COOH P Q+
2. H 2O 2. NaOH
+
3. H3O COOH
(A) P can be reduced to a primary alcohol using NaBH4.
(B) Treating P with conc. NH4OH solution followed by acidification gives Q.
(C) Treating Q with a solution of NaNO2 in aq. HCl liberates N2.
(D) P is more acidic than CH3CH2COOH. [JEE Advance 2022]
30. Considering the following reaction sequence [JEE Advance 2022]
NO2
P R H2 O
Q S T
H3C U
COOH
the correct option(s) is(are)

(A) P = H2/Pd, ethanol R = NaNO2/HCl U= 1. H3PO2 2.KMnO4–KOH, heat

N2Cl
(B) P=Sn/HCl R = HNO2 S=

H3C
 OH
N2Cl
(C) S = T= U = 1. CH3CH2OH
H3C H3C
2. KMnO4–KOH, heat
NO2 OH
(D) Q = R = H2/Pd, ethanol T=

HOOC H3C
1. A 2. A 3. D 4. A 5. A 6. C 7. C
8. A 9. D 10. A 11. D 12. A 13. C 14. B
15. A 16. B 17. B 18. C 19. D 20. A 21. D
22. A 23. A 24. D 25. D 26. 69.00 27. C 28. C
29. D 30. A 31. C 32. B 33. D 34. A 35. D
36. A 37. 7 38. C 39. A 40. B 41. C 42. A
43. A 44. A 45. B 46. D 47. B 48. A 49. B
50. B 51. D 52. C 53. D 54. 5 55. (A) 56. (D)
57. (A) 58. (A) 59. B 60. C 61. C 62. C 63. A
64. A 65. C 66. C 67. C 68. C 69. C 70. D
71. C 72. C 73. C 74. D 75. C 76. B 77. B
78. B 79. 2 80. A 81. C 82. B 83. C 84. C
1. C 2. C 3. C 4. C 5. B 6. B 7. D
8. C 9. D 10. C 11. AC 12. C 13. B,D 14. D
15. ABCD 16. C 17. D 18. BCD 19 B 20. C 21. 495
22. B,C 23. 18 24. 18.6 25. 6 26. AC 27. 1.31 28. 136.00
29. BCD 30. ABC
Alcohols & Ethers | JEE Main
1. HBr reacts with CH2 = CH – OCH3 under anhydrous conditions at room temperature to give -[AIEEE 2006]
(A) BrCH2CHO and CH3OH (B) BrCH2 – CH2 – OCH3
(C) H3C – CHBr – OCH3 (D) CH3CHO and CH3Br
Mg
2. In the following sequence of reactions, CH3CH2OH P A  B HCHO
 I2
  C H
2O
 D, then compound
ether
‘D’ is - [AIEEE 2007]

(A) butanal (B) n-butyl alcohol (C) n-propyl alcohol (D) propanal
3. A liquid was mixed with ethanol and a drop of concentrated H2SO4 was added. A compound with a fruity smell
was formed. The liquid was [AIEEE 2009]
(A) HCHO (B) CH3COCH3 (C) CH3COOH (D) CH3OH
4. From amongst the following alcohols the one that would react fastest with conc, HCl and anhydrous ZnCl 2 , is –
(A) 1- Butanol (B) 2- Butanol [AIEEE 2010]
(C) 2- Methylpropan -2-ol (D) 2- Methylpropanol
5. The main product of the following reaction is [AIEEE 2010]
C 6 H 5 CH 2 CH(OH)CH(CH 3 ) 2 conc
.H2SO4
  ?
H5C6CH2CH2 H5C6 H
(A) C = CH2 (B) C=C
H3C H CH(CH3)2
C6H5CH2 CH3 C6H5 CH(CH3)2

(C) C= C (D) C= C
H CH3 H H
6. Consider the following reaction :

C2H5OH + H2SO4  Product
Among the following which one cannot be formed as a product under any conditions ? [AIEEE 2011]
(A) Ethylene (B) Acetylene (C) Diethyl ether (D) Ethyl-hydrogen sulphate
7. The most suitable reagent for the conversion of R – CH2 – OH  R – CHO is : [JEE Main 2014]
(A) CrO3 (B) PCC (Pyridininum Chlorochromate)
(C) KMnO4 (D) K 2Cr2O7
8. 2-chloro-2-methylpentane on reaction with sodium methoxide in methanol yields : [JEE Main 2016]
(A) (B) (C)
(A) (A) and (C) (B) (C) only (C) (A) and (B) (D) All of these
9. The major product of the following reaction is : [JEE Main 2017]
(A) (B)
(C) (D)
10. The increasing order of the boiling points for the following compounds is : [JEE Main 2017]
(I) C2H5OH (II) C2H5Cl (III) C2H5CH3 (IV) C2H5OCH3
(A) (IV) < (III) < (I) < (II) (B) (III) < (II) < (I) < (IV)
(C) (III) < (IV) < (II) < (I) (D) (II) < (III) < (IV) < (I)
11. In the following reaction sequence :

KOH (aq) (i) CH3MgBr Anhy.ZnCl2 + Conc.HCl
I II +
III gives turbidity
(ii) H2O/H
(C3H6Cl2) immediately
The compound I is : [JEE Main 2017]
(A) (B)
(C) (D)
12. Phenol reacts with methyl chloroformate in the presence of NaOH to form product A. A reacts with Br2 to form
product B. A and B are respectively. [JEE Main 2018]
OH OH OH Br OH
and and
(A) OCH3 OCH3 (B) OCH3 OCH3
O Br O O O
O O O O
O O O O
O and O
(C) (D) O and O
Br Br
13. The product of the reaction given below is : [JEE Main 2019]
(A) (B) (C) (D)

14. The major product of the following reaction is [JEE Main 2019]
O
Hl (excess)

NC O
OH I I OH
(A) (B) (C) (D)
NC OH
NC OH NC I NC I
15. The synonym for water gas when used in the production of methanol is [JEE Main 2019]
(A) natural gas (B) laughing gas (C) syn gas (D) fuel gas
16. The major product of the following reaction is

CH3CH = CHCO2CH3  LiAIH4 [JEE Main 2019]

(A) CH3CH = CHCH2OH (B) CH 3CH2CH2CH2OH
(C) CH 3CH2CH2CO2CH 3 (D) CH3CH2CH2CHO
1. PBr3
OH 2. KOH (alc.)
OH
(A) (B) (C) (D)
HO O O O
O
Br
NaBH4
MeOH,25°C
O OH
Br OMe OMe O
(A) (B) (C) (D)

OCH3
Conc. HBr (excess)
Heat
CH=CH2
Br OH Br OH
(A) (B) (C) (D)
Br–CHCH3 Br–CHCH3 CH2CH Br CH2CH2Br
OH
20. CH3CH2 C CH3 cannot be prepared by [JEE Main 2019]
Ph
(A) CH3CH2COCH3 + PhMgX (B) PhCOCH3 + CH3CH2MgX

(C) PhCOCH2CH3 + CH3 + CH3MgX (D) HCHO + PhCH(CH3) CH2MgX
21. What will be the major product when m-cresol is rected with propargyl bromid (HC  C –– CH2Br) in presence
of K2CO3 in acetone ? [JEE Main 2019]
OH
OH
O OH
(A) (B) (C) (D)
H3C
H3C
CH3 CH3
22. Which of the following compounds reacts with ethyl magnesium bromide and also decolourises bromine water
solution [JEE Main 2019]
CN OCH3 OH CN O
CH2––CO2CH3 CH
(A) (B) CH2 (C) (D)
23. An organic compound ‘A’ (C9H10O) when treated with conc. HI undergoes cleavage to yield compound ‘B’ and
‘C’. ‘B’ gives yellow precipitate with AgNO3 where as ‘C’ tautomerizes to ‘D’. ‘D’ gives positive iodoform test.
‘A’ could be: [JEE Main 2020]
(A) O—CH2—CH—
— CH2 (B) CH2—O—CH —
—CH2
(C) (D) H3C O—CH —

—CH2
24. An organic compound (A) (molecular formula C6H12O2) was hydrolysed with dil. H2SO4 to give a carboxylic
acid (B) and an alcohol (C). ‘C’ gives white turbidity immediately when treated with anhydrous ZnCl2 and conc.
HCl. The organic compound (A) is : [JEE Main 2020]
(A) (B) (C) (D)
25. Which of the following derivatives of alcohols is unstable in an aqueous base ? [JEE Main 2020]
(A) (B) RO – CMe3 (C) (D)
26. Which is the final product (major) ‘A’ in the given reaction ? [JEE-Mains (24-Feb_Shift -1)2021]
OH
CH 3
CH
HCl
CH3 ‘A’
(major Product)
CH3 CH 3
CH CH2 CH–CH 3
(A) (B)
CH3 Cl
Cl CH3
CH
(C) (D)
CH 2 – CH3 CH 3
27. Identify the major products A and B respectively in the following reaction of phenol :
OH
(i) CHCl 3, NaOH Br2 in CS 2
B A
(ii) H 3O + 273K
OH OH
CHO OH OH
and Br CHO
(A) (B) and
Br
OH OH OH OH
Br
and and
(C) (D)
CHO Br CHO
28. Main Products formed during a reaction of 1-methoxy naphthalene with hydroiodic acid are :
(A) and CH3I (B) and CH3OH
(C) and CH3OH (D) and CH3I
Enzyme A
29. C12 H 22O11  H 2O  C6 H12O6  C6 H12O6 [JEE-Mains (17-March_Shift -2)2021]
Sucrose Glu cos e Fructose
Enzyme B
C6 H12O6   2C2 H 5OH  2CO2
Glu cos e
In the above reactions, the enzyme A and enzyme B respectively are:

(A) Invertase and Amylase (B) Amylase and Invertase
(C) Invertase and Zymase (D) Zymase and Invertase Zymase Invertase
30. Given below are two statements : [JEE-Mains (17-March_Shift -2)2021]

Statement I : 2-methylbutane on oxidation with KMnO4 gives 2-methylbutan-2-ol.
Statement II : N-alkanes can be easily oxidized to corresponding alcohols with KMnO4.
Choose the correct option :
(A) Both statement I and statement II are incorrect
(B) Statement I is correct but statement II is incorrect
(C) Both statement I and statement II are correct
(D) Statement I is incorrect but statement II is correct
31. Which one of the products of the following reactions does not react with Hinsburg reagent to form sulphonamide?
CN CN
C2 H5OH
+ Na/Hg
+ H2/Ni
(A) (B)
CH3
NO 2
CN
CN 
H 3O
+ LiAlH4
(C) + SnCl2 +HCl (D)
CHO
32. Which one of the following is correct structure of cytosine ? [JEE-Mains (25-July_Shift-2)2021]
O NH2
H2N
N H3C
N–H N N
(A) N O (B) (C) (D)
H N O O H3C N O
N
H H H
OH
33.
H3 PO 4

120 C
  MajorA
Pr oduct 
 (BH 3 ) 2
H 2 O 2 / OH , H 2 O
 P
 Major Pr oduct 
Consider the above reaction and identify the product P : [JEE-Mains (27-July_Shift-1)2021]
OH CH3 CH3 OH
OH
OH OH
(A) (B) (C) (D)
34. Consider the below reaction, and choose the correct statement: [JEE-Mains (27-July_Shift-2)2021]
(A) The reaction is not possible in acidic medium

(B) Both compounds A and B are formed equally
(C) Compound B will be the major product
(D) Compound A will be the major product
Consider the above reaction, the major product “P” formed is:
(A) (B)
(C) (D)
36. In the following sequence of reactions, the final product D is : [JEE-Mains (27-August_Shift-1)2021]
OH
Br CH3 H2/Pd-C CrO 3

CH3 – CHC–H+NaNH2  A B C D
O
(A) H 3C– CH2 – CH 2– CH2 – CH2 – C – H
(B) CH3– CH=CH – CH2– CH2 – CH2 – COOH

O
(C) CH 3– CH2 – CH2 – CH 2– CH2 – C – CH3
(D) H3C – CH = CH – CH(OH) – CH2 – CH2 – CH3

37. The major product formed in the following reactions is : [JEE-Mains (31-August_Shift-1)2021]
CH3
conc. H2SO4
CH3 C CH CH3 Major Product
a few drops
CH3 OH
CH3 CH3 CH 3
CH3 C CH CH 2
(A) (B)
CH3 H3 C CH3
CH 3
(C) C CH CH3 (D) CH3 C CH CH 2CH3

CH3
CH3
38. The major product formed in the following reaction, is [JEE-Mains (25-Jun-Shift-2)2022]
+
OH + H
O
(A) (B)
O OH
O
O
(C) H3C (D)
O H O O
39. Given below are two statemetns : [JEE-Mains (25-July_Shift-1)2022]

Statement I : On heating with KHSO4, glycerol is dehydrated and acrolein is formed.
Statement II : Acrolein has fruity odour and can be used to test glycerol’s presence.
Choose the correct option
(A) Both statement I and Statement II are correct
(B) Both Statement I and Statement II are incorrect
(C) Statement I is correct but Statement II is incorrect
(D) Statement I is incorrect but Statement II is correct
40. Which of the following can be used to prevent the decomposition of H2O2 ?
(A) Urea (B) Formaldehyde (C) Formic acid (D) Ethanol
NaNO .HCl
1. (X)C5H13N     (Y) (Tertiary alcohol + other products)
2
N2
(Optically active)
Find X and Y. Is Y optically active ? Write the intermediate steps. [JEE 2005]
AlCl3 (i) O / 
2. + Cl – CH2CH2–CH3   P 2   Q + Phenol
The major products P and Q are - [JEE 2006]
(A) and CH3CH2CHO (B) and CH3COCH3
(C) and CH3COCH3 (D) and CH3CH2CHO3.
3. Satement-1 : p-Hydroxybenzoic acid has a lower boiling point than o-hydroxybenzoic acid. because
Statement-2 : o-Hydroxybenzoic acid has intramolecular hydrogen bonding. [JEE 2007]
(A) Statement-1 is true, Statement-2 is True; Statement-2 is a correct explanation for Statement-1
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1.
(C) Statement-1 is True, Statement-2 is false.
(D) Statement-1 is False, Statement-2 is True.
4. Column-I Column-II [IIT 2009]

(A) CH 3CH2CH2CN (P) Reduction with Pd-C/H2
(B) CH3CH2OCOCH 3 (Q) Reduction with SnCl2/HCl
(C) CH 3–CH=CH–CH2OH (R) Development of foul smell o n treatment with chloroform and alcoholic
KOH
(D) CH 3CH2CH2CH2NH2(s) (S) Reduction with diisobutylauminium hydride (DiBAL-H)
(T) Alkaline hydrolysis
5. Match the chemical conversions in List with the appropriate reagent in List II and select the correct answer using
the code given below the lists : [JEE Adv. 2013]
List I List II
P. 1. (i) Hg(OAc)2; (ii) NaBH2
Q. 2. NaOEt
R. 3. Et-Br
S. 4. (i) BH3; (ii) H2O2/NaOH

Codes :
P Q R S
(A) 2 3 1 4
(B) 3 2 1 4
(C) 2 3 4 1
(D) 3 2 4 1
6. The acidic hydrolysis of ether (X), shown below is fastest when [JEE Adv. 2014]
(A) one phenyl group is replaced by a methyl group.

(B) one phenyl group is replaced by a para-methoxyphenyl group
(C) two phenyl groups are replaced by two para-methoxyphenyl groups
(D) no structural change is made to X
7. The correct combination of names of isomeric alcohols with molecular formula C4H10O is/are:
(A) tert-butanol and 2-methylpropan-2-ol [JEE Adv. 2014]
(B) tert-butanol and 1, 1-dimethylethan-1-ol
(C) n-butanol and butan-1-ol
(D) isobutyl alcohol and 2-methylpropane-1-ol
8. The number of hydroxyl group(s) in Q is [JEE Adv. 2015]
P Q
9. The major product of the reaction is [JEE Adv. 2015]

H3C CO2H
CH 3 NH 2
H3C NH 2 H3C CO2H

(A) (B)
CH3 OH CH 3 OH
H3C CO2H
(C) (D) None of these
CH 3 OH
10. The desired product X can be prepared by reacting the major product of the reactions in LIST-I with one or
more appropriate reagents in LIST-II.
(given, order of migratory aptitude: aryl > alkyl > hydrogen) [JEE Advance 2018]
O
Ph
OH
Me Ph
X
LIST-I LIST-II
Ph
HO
P. Me + H2SO4 1. I2, NaOH
Ph
OH
Me
Ph
H2N
Q. H + HNO2 2. [Ag(NH3)2]OH
Ph
OH
Me
Ph
HO
R. Ph + H2SO4 3. Fehling solution
Me
OH
Me
Ph
Br
H + AgNO3
Ph
S. 4. HCHO, NaOH
OH
Me
5. NaOBr
The Correct options is
(A) P  1; Q  2,3; R  1, 4; S  2,4
(B) P  1,5; Q  3, 4; R  4, 5; S3
(C) P  1,5; Q  3,4; R  5; S  2, 4
(D) P  1,5; Q  2,3; R  1, 5; S  2,3
11. Choose the correct option(s) for the following set of reactions [JEE Advanced 2019]
(i) MeMgBr conc. HCl
C6H10O O s
(ii) H2O (major)
20% H3PO4, 360 K
(i) H2, Ni HBr, benzolyl peroxide

T R s
(major) (ii) Br2,hv (major) (major)
H3 C Br CH3 CH3 H3C Br

Cl Cl
(A) (B)
U S S T
H3C Cl CH3 CH3 H3C Br

Br Br
(C) (D)
S U U T
1. D 2. C 3. C 4. C 5. B 6. B 7. B
8. D 9. A 10. C 11. A 12. D 13. A 14. D
15. C 16. A 17. C 18. D 19. B 20. D 21. A
22. C 23. B 24. A 25. A 26. C 27. A 28. D
29. C 30. B 31. C 32. C 33. C 34. D 35. C
36. C 37. B 38. D 39. C 40. A
OH
|
1. X : C– C – C  C Y : C– C  C  C 2. C 3. D
| | |
C NH2 C
4. A  Q, S, T ; B  S, T; C  P., D  R Y is optically inactive
5. A 6. C 7. ACD 8. 4 9. C 10. D 11. CD

Grignard Reagent | JEE Main
1. Which of these will not react with acetylene ? [AIEEE-2002]

(A) NaOH (B) ammonical AgNO3 (C) Na (D) HCl
2. CH3 – Mg – Br is an organo metallic compound due to [AIEEE-2002]

(A) Mg – Br bond (B) C – Mg bond (C) C – Br bond (D) C – H bond
3. Ethyl isocyanide on hydrolysis in acidic medium generates [AIEEE-2003]

(A) ethylamine salt and methanoic acid (B) propanoic acid and ammonium salt
(C) ethanoic acid and ammonium salt (D) methylamine salt and ethanoic acid
4. Rate of the reaction [AIEEE-2004]
O O
R  Nu  R Z

Z Nu
is fastest when Z is [AIEEE-2004]

(A) Cl (B) OCOCH3 (C) OC2H5 (D) NH2
5. Acetyl bromide reacts with excess of CH3MgI followed by treatment with a saturated solution of NH4Cl given
(A) acetone (B) acetyl iodide [AIEEE-2004]
(C) 2- methyl -2- propanol (D) acetamide
6. Phenyl magnesium bromide reacts with methanol to give [AIEEE-2006]

(A) a mixture of anisole and Mg(OH)Br (B) a mixture of benzene and Mg(OMe)Br
(C) a mixture of toluene and Mg(OH)Br (D) a mixture of phenol and Mg(Me)Br
7. In the following sequence of reactions, [AIEEE-2007]

P l2 Mg HCHO H2O
CH3CH2OH   A 
 B   C  D
ether
the compound ‘D’ is :

(A) butanal (B) n-butyl alcohol (C) n-propyl alcohol (D) propanal
8. Which one of the following is the strongest base in aqueous solution? [AIEEE-2007]
(A) Trimethylamine (B) Aniline (C) Dimethylamine (D) Methylamine
9. The treatment of CH3MgX with CH3C  C–H produces [AIEEE-2008]

(A) CH3 – CH = CH2 (B) CH3C  C – CH3
H H
(C) CH3—C C—CH3 (D) CH4
10. A major component of Borsch reagent is obtained by reacting hydrazine hydrate with which of the
following ? [IIT Mains Online 2013]
Cl Cl
Cl Cl
O2N NO2 NO2
O2N NO2 NO2
(A) (B) (C) (D)
NO2 NO2
11. The hydrocarbon with seven carbon atoms containing a neopentyl and a vinyl group is :
[IIT-JEE Mains (online) 2016]
(A) 2, 2-dimethyl-4-pentane (B) 4, 4-dimethylpentene
(C) Isopropyl-2-butene (D) 2, 2-dimethyl-3-pentene
12. The “N” which does not contribute to the basicity for the compound is :
[IIT-JEE Mains (online) 2016]
(A) N7 (B) N1 (C) N9 (D) N3
13. The gas evolved on heating CH3MgBr in methanol is [JEE Mains (online) 2016]
(A) Methane (B) Ethane (C) Propene (D) HBr
14. The major product B formed in the following reaction sequence is [JEE Main (online) 2018]
CHO
(i) C2H5MgBr
A HCl B
(ii) H2O
MeO
Cl
(A) (B) Cl
MeO Cl
(C) (D)
MeO MeO
Br
15. The product formed in the first step of the reaction of CH3 —CH 2—CH—CH2—CH—CH3 with excess Mg/
Br
Et2O(Et =C2H5) is : [JEE-Mains (24-Feb_Shift -1)2021]
CH3—CH2—CH—CH 2—CH—CH3 CH3 —CH2—CH—CH 2—CH—CH 3
(A) (B)
CH3—CH—CH 2—CH—CH 2—CH3 CH3 —CH2—CH—CH 2—CH—CH 3
MgBr
CH2
(C) CH3CH 2—CH—CH2–CH—CH3 (D) CH3 —CH
CH—CH3
MgBr
CN
(i)C 6H5MgBr Ether
(1.0equivalent),dry
16. 

 X
(ii) H3O Major Pr oduct
OCH3
The structure of X is: [JEE-Mains (16-March_Shift -2)2021]
O
O
C6H5 NH2 NH2
C6H5
(A) (B) (C) (D)
C6 H5
OCH3 OCH3 C6H5
17. Reaction of Grignard reagent, C2H5MgBr withC8H8O followed by hydrolysis is gives compound “A” which
reacts instantly with Lucas reagent to give compound B, C10H13Cl. The Compound B is :
(A) (B) (C) (D)
18. To synthesise 1.0 mole of 2-methylpropan-2-ol from Ethylethanoate ___________ equivalents of CH3MgBr
reagent will be required. (Integer value) [JEE-Mains (20-July_Shift -1)2021]
19. Which one of the following compounds will provide a tertiary alcohol on reaction with excess of CH3MgBr
followed by hydrolysis ? [JEE-Mains (22-July_Shift-2)2021]
O
O CH3
(A) (B) O
O
O OCH2CH3
CH3 NC
C
(C) (D)
OH CH
O
(i) C2H 5MgBr, dry ether
(ii) H2 O, HCl P
20. (Major Product)
Consider the above reaction, the major product ‘P’ is:– [JEE-Mains (25-July_Shift -1)2021]
OH OH
(A) (B) H
OH
OH
H
(C) (D) Cl
Cl
H
21. The correct sequence of correct reagents for the following transformation is
(A) (i) Fe, HCl(ii) NaNO2, HCl, 0°C(iii) H2O/H+(iv) Cl2, FeCl3
(B) (i) Cl2, FeCl3(ii) NaNO2, HCl, 0°C(iii) Fe, HCl(iv) H2O/H+
(C) (i) Fe, HCl(ii) Cl2, HCl(iii) NaNO2, HCl, 0°C(iv) H2O/H+
(D) (i) Cl2, FeCl3(ii) Fe, HCl(iii) NaNO2, HCl, 0°C(iv) H2O/H+
22. Which one of the following is the major product of the given reaction?
CH3
(i) 2CH 3MgBr
NC O +
(ii) H3O
Major Product [JEE-Mains (27-August_Shift-2)2021]
(iii) H 2SO4,heat
CH3
O CH 3 CH3
CH 3 NC CH 3
CH3
(A) (B)
CH3 CH 3
CH3 O CH 3
NC CH 3 CH 3
CH3
(C) (D)
CH 3 CH3
23. Given below are two statements : [JEE-Mains (27-August_Shift-2)2021]
Statement I : Ethyl pent-4-yn-oate on reaction with CH3MgBr gives a 3°alcohol.
Statement II : In this reaction one mole of ethyl pent-4-yn-oate utilizes two moles of CH3MgBr.
In the light of the above statements choose the most appropriate answer from the options given
below :
(A) statement I is true but statement II is false
(B) both statement I and statement II are true
(C) both statement I and statement II are false
(D) statement I is false but statement II is true
24. Which one of the following reactions will not yield propionic acid? [JEE-Mains (27-August_Shift-2)2021]
(A) CH3CH2CH2Br+Mg,CO2 dry ether/H3O+
(B) CH 3CH2CCl3+OH-/H3O+
(C) CH 3CH2COCH3+Ol-/H3O+
(D) CH3CH2CH3+KMnO4(Heat),OH -/H3O+
25. In the given reaction [JEE-Mains (25-Jun-Shift-2)2022]

OH
(i) 2 Mg, THF C

2A
(ii) Methyl benzoate
+
(iii) H 2O / H
‘A’ can be
(A)benzyl bromide (B)bromobenzene (C)cyclohexyl bromide (D) methyl bromide
26. Which of the following conditions or reaction sequence will NOT give acetophenone as the major
product? [JEE-Mains (25-Jun-Shift-2)2022]
O O
(A) C 6H5 H + CH3MgBr (b) Na2Cr2O 7, H

+
(B) H3C H + C 6H 5MgBr (b) PCC, DCM
O O
(C) C 6H5 OC 2H 5 + 2 CH 3 Mg Br (D) C 6H5 Cl + CH 3MgBr + CdCl 2
O CH2
MgBr
H2 O
+ CH 3 C CH 2 C CH3 'A' 'B'
27.
Major Product
MgBr
Consider the above reaction sequence and identify the product B
OH
OH
OH O O
H3C
(A) HO CH3 (B) (C) (D)

CH3 H3C CH3
H3C OH
OH
Br COOH
(CH3)3 CLi (i) CO 2
[A]
28. (ii) H 3 O
+
OH OH
In the given conversion the compound A is : [JEE-Mains (29-Jun-Shift-1)2022]
Li Li Br C(CH3 )3
(A) (B) (C) (D)

OH OLi OC(CH3 )3 OH
29. The number of chiral alcohol(s) with molecular formula C4H10O is

+
CH3MgBr H3O Zn Hg
30. H3C CH2 CN A B C [JEE-Mains (25-July_Shift-2)2022]
Ether HCl
The correct structure of C is
O
(A) H3C CH2 CH2 CH3 (B) H3C CH2 C CH3

OH
(C) H3C CH2 CH CH3 (D) H3C CH2 CH CH2
31. Which reactant will give the following alcohol on reaction with one mole of phenyl magnesium bromide
(PhMgBr) followed by acidic hydrolysis ? [JEE-Mains (26-July_Shift-1)2022]
Ph
Ph C OH
CH3
O
(A) H3C C N (B) Ph C N (C) H3C C O Ph (D) Ph C CH3
O
32. Compound ‘A‘ undergoes following sequence of reactions to give compound ‘B‘. The correct structure
and chirality of compound ‘B‘ is [where Et is –C2H5] [JEE-Mains (29-July_Shift-2)2022]
(i) Mg, Et 2O
B
(ii) D 2O
Br
(A) , Achiral (B) , Chiral (C) , Chiral (D) OD, Achiral

D OD D
1. Write the structural formula of main organic product formed when ethyl acetate is treated with double the molar
quantity of methyl magnesium bromide and the reaction mxiture is poured into water. [JEE 1981]
2. Identify the major product. [JEE 1993]

C6H5COOH + CH3MgI  ? + ?
3. Predict the major product. [JEE 1994]

( i ) CH MgBr ( excess )
C6H5– CH2COCH3  3  
 
(ii ) H
4. Which of the following is an organometallic compound? [JEE 1997]

(A) Lithium methoxide (B) Lithium acetate
(C) Lithiumdimethylamide (D) Methyl lithium
5. (CH3)3CMgCl on treatment with D2O produces [JEE 1997]

(A) (CH3)3CD (B) (CH3)3COD (C) (CD)3CD (D) (CD)3COD
6. C4 H 8O 2 CH MgBr
3 P, the product 'P' will be [JEE 2003]
Ethyl ester (excess)
(A) (B) (C) (D)
7. Order of rate of reaction of following compounds with phenyl magnesium bromide is: [JEE 2004]
Ph  C  Ph Me  C  H Me  C  Me
|| || ||
O O O
(I) (II) (III)
(A) I > II > III (B) II > III > I (C) III > I > II (D) II > I > III
CH 3
|
8. Ph – MgBr + CH3  C  OH  A [JEE 2005]
|
CH 3
CH 3 CH 3
| |
(A) (B) CH 3  C  OPh (C) (D) CH 3  C  Ph
| |
CH 3 CH 3
9. Identify the reaction mechanism : [JEE 2011]
10. The major product in the following reaction is [JEE Advance 2014]
O
Cl 1
. CH 3MgBr , dry ether , 0 C
  
CH3 2. aq. acid
O OH
(A) H3C (B) H C CH3
CH3 2 CH3
CH3
(C) (D)
O CH2 O CH3
Paragraph for question nos. 11 & 12

In the following reactions : [JEE Advance 2015]
C8 H 6 Pd
BaSO 4
 C8 H 8 i
. B2 H 6
  X
H2 ii . H 2O 2 , NaOH , H 2O
 H 2O
 HgSO 4 , H 2SO 4
C8 H8O i
. EtMgBr , H 2O
      Y
ii . H  , Heat
11. Compound X is
O OH
(A) CH3 (B) CH3
OH
CHO
(C) (D)
12. The major compound Y is
(A) CH 3 (B) CH 3
CH2 CH3
CH3
(C) (D) CH3
1. A 2. B 3. A 4. A 5. C 6. B 7. C
8. C 9. D 10. D 11. B 12. C 13. A 14. A
15. C 16. A 17. D 18. 2 19. B 20. C 21. D
22. A 23. A 24. A 25. B 26. C 27. A 28. B

29. 2/1 30. A 31. D 32. A
O
||
H O
1. CH 3  C  OC2 H 5  2CH 3MgBr  
2
 ]
OH
|
C6 H 5  CH 2 — C — CH 3
2. C6H5COO¯ Mg I + CH4 3. |
CH 3
4. D 5. A 6. A 7. B 8. A
O O CH2–Cl O
|| CH3MgI Cl  Ph
9. Ph  C  CH 2  CH 2  CH 2  Cl   Ph – C – CH2CH2 
H3 C
CH3
10. D 11. C 12. D
Carbonyl Compound | JEE Main
1. The best reagent to convert pent–3–en–2–ol into pent–3–in–2–one is - [AIEEE-2005]
(A) Acidic dichromate
(B) Acidic permanganate
(C) Pyridinium chloro–chromate
(D) Chromic anhydride in glacial acetic acid
2. The increasing order of the rate of HCN addition to compounds A – D is - [AIEEE 2006]
(a) HCHO (b) CH3COCH3 (c) PhCOCH3 (d) PhCOC6H5
(A) d < b < c < a (B) d < c < b < a (C) c < d < b < a (D) a < b < c < d
3. Which of the folowing on heating with aqueous KOH, produces acetaldehyde ? [AIEEE 2009]
(A) CH3COCl (B) CH3CH2Cl (C) CH2ClCH2Cl (D) CH3CHCl2
4. Which compound would give 5 - keto - 2 - methyl hexanal upon ozonolysis ? [JEE Main 2015]
CH3 CH 3
CH3 CH3
CH3 H3C
(A) (B) (C) (D)
CH3 CH3
5. In the following sequence of reactions: [JEE Main 2015]

KMnO4 SOCl2
Toluene A B
H2/Pd BaSO4
C
the product C is:
(A) C6H5COOH (B) C6H5CH3 (C) C6H5CH2OH (D) C6H5CHO
6. In the reaction [JEE Main 2015]

NH2
NaNO2/HCl
D
0 - 5°C
CuCN/KCN
CH3
E + N2
the product E is:
COOH CN
CH3
(A) (B) H3C CH 3 (C) (D)

CH3 CH3
7. The correct sequence of reagents for the following conversion will be : [JEE Main 2017]
(A) CH3MgBr, H+/CH3OH, [Ag(NH3)2]+OH– (B) CH3MgBr, [Ag(NH3)2]+OH– , H+/CH3OH

(C) [Ag(NH3)2]+OH–, CH3MgBr, H+/CH3OH (D) [Ag(NH3)2]+OH–, H+/CH3OH, CH3MgBr
8. The major product of the following reaction is [JEE-MAIN 2019]
HO (i) CrO 3
(ii) SoCl 2/
(iii) 
HO
O O
O O
(A) (B) (C) (D)
HO Cl
HO Cl
9. The major product Y in the following reaction is [JEE-MAIN 2019]

Ph CH3
NaOCl (i) SOCl2
X (ii) Aniline Y
O
O NH2
Ph
N NH2 Ph
HN Ph
O
O
(A) (B) (C) (D)
Ph
O
Ph
10. The major product of the following reaction is [JEE-MAIN 2019]

O
O HO CH3
NaBH4
EtOH
HO CH3
CHO
CHO
OH
OH O OH
(A) (B) (C) (D)
OEt
11. The increasing order of the following compounds towards HCN addition is : [JEE-MAIN 2020]
(i) (ii) (iii) (iv)
(A) (iii) < (i) < (iv) < (ii) (B) (i) < (iii) < (iv) < (ii)
(C) (iii) < (iv) < (ii) < (i) (D) (iii) < (iv) < (i) < (ii)
12. The increasing order of the reactivity of the following compounds in nucleophile addition reaction is:
Propanal, Benzaldehyde, Propanone, Butanone [JEE-MAIN 2020]
(A) Benzaldehyde > Butanone < Propanone < Propanal
(B) Butanone < Propanone < Benzaldehyde < Propanal
(C) Benzaldehyde < Propanal < Propanone < Butanone
(D) Propanal < Propanone < Butanone < Benzaldehyde
13. The compound A in the following reactions : [JEE-MAIN 2020]
(A) (B)
(C) (D)
14. The number of chiral centres present in [B] is .............. [JEE-MAIN 2020]
15. Consider the following reactions : [JEE-MAIN 2020]
(I2 + NaOH)
'B' yellow ppt

Ag2O
silver mirror

(I2 + NaOH)

no yellow ppt
'C'
LiA1H4 Anhydrous ZnCl2
'D' gives white turbidity
& Conc. HCl
within 5 minutes
‘A’ is
(A) (B)
(C) (D)
16. The correct match between Item – I (starting material) and Item-II (reagent) for the preparation of
benzaldehyde is: [JEE-MAIN 2020]
Item-I Item-II
(I) Benzene (P) HCl and SnCl 2, H3O+
(II) Benzonitrile (Q) H2, Pd-BaSO4,S and quinoline
(III) Benzoyl Chloride (R) Co, HCl and AlCl3
(A) (I)-(R), (II)-(Q) and (III)-(P) (B) (I)-(Q), (II)-(R) and (III)-(P)
(C) (I)-(P), (II)-(Q) and (III)-(R) (D) (I)-(R), (II)-(P) and (III)-(Q)
17. Identify products A and B. [JEE-Mains (24-Feb_Shift -1)2021]

CH3
dil.KMnO4 CrO3
A B
273K
CH3 CH3
A: B:
(A)
OH O
CH3 CH3
A : OH B: OH
(B)
OH O
O O
(C) A : OHC –CH2 CH2CH 2–C –CH 3 B : HOOC–CH2CH 2CH2–C–CH 3
CH3 CH3
A : OH B:
(D)
OH O
18. Which of the following reagent is used for the following reaction ?
CH3CH2CH3  ?
 CH3CH2CHO [JEE-Mains (24-Feb_Shift -1)2021]
(A) Potassium permanganate (B) Molybdenum oxide
(C) Copper at high temperature and pressure (D) Manganese acetate
19. The major product of the following reaction is : [JEE-Mains (25-Feb_Shift -2)2021]
H2 /CO
CH3CH2CH=CH2
Rh catalyst
(A) CH3CH2CH2CHO (B) CH3CH2CH=CH–CHO

(C) CH3CH2CH2CH2CHO (D) CH3 CH2C=CH2
CHO
20. Which one of the following reactions will not form acetaldehyde ?
CrO3 – H2SO4 i) DIBAL-H

(A) CH3CH 2OH (B) CH 3CN
ii) H 2O
Pd(II)/Cu(II) Cu
(C) CH 2 = CH2 + O2 (D) CH 3CH2OH
H2O 573 K
21. Consider the following chemical reaction. [JEE-Mains (25-Feb_Shift -1)2021]

HC CH  Product
(1)Red hot Fe tube,873K
(2)COHCl/AlCl3
The number of sp2 hybridized carbon atom(s) present in the product is _______.
22. Identify A in the following chemical reaction. [JEE-Mains (26-Feb_Shift -2)2021]

CHO
i) HCHO, NaOH
ii) CH3CH2Br,NaH, DMF

CH3O iii) HI, 
O
CH 2OH
C–OCH2CH 3
(A) (B)
CH3O
HO
CH 2I CH2OH
(C) (D)
HO HO
23. Identify A in the given chemical reaction. [JEE-Mains (26-Feb_Shift -2)2021]

CH 2 CH 2CHO
NaOH
 A (Major product )
C2H5OH,H2O

CH 2 CH2 CHO
O
O
C—H
(A) (B)
O
CHO CH 2 CH2COOH
(C) (D)
CH2CH2 CH2OH
Hydrolysis
24. A 
373 K
 B [JEE-Mains (26-Feb_Shift -1)2021]
(C 4H8Cl2 ) (C 4H8 O )
B reacts with Hydroxyl amine but does not give Tollen’s test. Identify A and B.
(A) 1, 1-Dichlorobutane and 2-Butanone (B) 2, 2- Dichlorobutane and Butan-2-one
(C) 2, 2- Dichlorobutane and Butanal (D) 1, 1- Dichlorobutane and Butanal
Consider the above reaction, the product ‘X’ and ‘Y’ respectively are :
(A) (B)
(C) (D)
O O
Ethylene Glycol
26. A
OC2H 5 H+ (Major Product)
The product “A” in the above reaction is : [JEE-Mains (17-March_Shift -1)2021]
OH
O O
OH O
(A) (B) O O
OC2 H5 OC2H 5
O
(C) O O (D) OC2H5
OH
OH
27. The total number of C–C sigma bond/s in mesityl oxide (C6H10O) is …… (Round off to the Nearest Integer).
OH
CHO O
28. OH
OH
(I) (II) (III) (IV) [JEE-Mains (20-July_Shift -1)2021]
Which among the above compound/s does/do not form Silver mirror when treated with Tollen’s reagent?
(A) Only (II) (B)(I), (III) and (IV) only
(C)(III) and (IV) only (D)Only (IV)
29. The number of nitrogen atoms in a semicarbazone molecule of acetone is ___ _

30. The major product (P) in the following reaction is :
O
CHO
(i) (KOH (alc.). P
+
O (ii) H , ? ? (major product) [JEE-Mains (20-July_Shift-2)2021]
O 0 CHO O
(A) OHC (B) (C) (D)
O
O
0
CH3CHO ‘P’ (i ) I2 /NaOH, Filter

31. NaOH (ii) Filtrate + HCl
X
(Major Product)
Consider the given reaction, the product ‘X’ is: [JEE-Mains (25-July_Shift -1)2021]
OH O O
(A) CHO (B)

H
O OH O O
(C) (D) OH
32. A reaction of benzonitrile with one equivalent CH3MgBr followed by hydrolysis produces a yellow liquid
“P”. The compound “P” will give positive. [JEE-Mains (25-July_Shift-2)2021]
(A)Tollen’s test (B)Schiff’s test (C)Ninhydrin’s test (D)Iodoform test
Br CHO EtOHexcess "A" t – 

"B "
33. 
dryHClgas
 (major product) 
BuO K
 (major product)
[Where Et –C2H5 tBu (CH3)3C–]
Consider the above reaction sequence, Product “A” and Product “B” formed respectively are :
OE t H2C OEt OEt OEt

Br Br t
BuO
(A) OEt
, OEt
(B) OEt
, OEt
Ot Bu OEt H2 C OEt
EtO EtO
(C) EtO CHO
, OH
(D) OEt OEt
,
34. Which one of the following compounds will give orange precipitate when treated with 2, 4-dinitrophenyl
hydrazine? [JEE-Mains (27-July_Shift-1)2021]
O OH
O O
C–OH
OCH2 CH3 CH3
(A) OCH 2CH 3 (B) (C) (D)
OH O
( i) DIBAL  H
35. R  CN (ii) H O
RY [JEE-Mains (27-July_Shift-2)2021]
2
Consider the above reaction and identify “Y”

(A) –CHO (B) –CONH2 (C) –CH2NH2 (D) –COOH
36. The major products formed in the following reaction sequence A and B are :
O
CH3 Br2
A+B
KOH
Br O HO O
A= C—CH 3 , B= C—CH 3
(A) Br HO
O
A= C , B = CHBr3
(B)
OK
O
A= C—CBr3 , B= CHO
(C)
O O
A= C—CH2–Br , B= C—CH2–OH
(D) Br Br
37. Match List –I with List – II [JEE-Mains (26-August_Shift-2)2021]
List – I List – II
(Chemical Reaction) (Reagent used)
(a) CH3COOCH2CH3  CH3CH2OH (i) CH3MgBr/H3O+(1 equivalent)
(b) CH3COOH3CH3CHO (ii) H2SO4/H2O
(c) CH3C  NCH3CHO (iii) DIBAL-H/H2O
O
(d) CH3C=NCH3 CH3 (iv) SnCl2,HCl/H2O
Choose the most appropirate

(A) (a)-(iii), (b)-(ii), (c)-(i), (d)-(iv) (B) (a)-(ii), (b)-(iii), (c)-(iv), (d)-(i)
(C) (a)-(iv), (b)-(ii), (c)-(iii), (d)-(i) (D) (a)-(ii), (b)-(iv), (c)-(iii), (d)-(i)
O OH
"X" CN LiAlH 4
38. "y"
H +
HCN,H2O H H 3O
(Major Product)
Consider the given reaction, Identify ‘X’ and ‘Y’ : [JEE-Mains (26-August_Shift-2)2021]
OH
OH
NH 2
(A) X-NaOH Y- (B) X-NaOH Y- NH 2
H H
OH OH
NH2
(C) X-HNO3 Y- H NH2 (D) X-HNO3 Y-
H
NH2
(CH3CO)2 O P
(Major Product)
39. NH2
O
The Major Product in the above reaction is :

NHCOCH3
NH3CH3 COO-
(A) (B) NH2

NHCOCH3
O
O
NH2 NHCOCH3
(C) NHCOCH3 (D) NHCOCH3
O O
40. The structure of the starting compound P used in the reaction given below is :
1.NaOCl
P OH
2.H3O
+
O
O
H
(A) (B)
O
O
(C) (D)
O
41. The major products A and B in the following set of reactions are :
OH +
LiAlH 4 H3 O
A B
H3 O+ H 2SO4
CN [JEE-Mains (31-August_Shift-1)2021]
OH OH
A= , B=
(A) CHO CO2H
OH OH
A= , B=
(B)
NH2 CHO
OH OH
(C) A = , B=
OH CHO
OH
(D) A = , B= COOH
NH 2
42. For the reaction given below: [JEE-Mains (31-August_Shift-2)2021]
CHO
1. NaOH, 
Product
2. H 3O+
CH2OH
The compound which is not formed as a product in the reaction is a:

(A) Compound with both alcohol and acid functional groups
(B) dicarboxylic acid
(C) diol
(D) monocarboxylic acid
43. Given below are two statements: [JEE-Mains (1-September_Shift-2)2021]

Statement I : The nucleophilic addition of sodium hydrogen sulphite to an aldehyde or a ketone
involves proton transfer to form a stable ion.
Statement II: The nucleophilic addition of hydrogen cyanide to an aldehyde or a ketone yields
amine as final product.
In the light of the above statements, choose the most appropriate answer from the option given
below:
(A) Statement I is false but Statement II is true.
(B) Statement I is true but Statement II is false.
(C) Both Statement I and Statement II are true.
(D) Both Statement I and Statement II are false.
44. In the following sequence of reactions a compound A, (molecular formula C6H12O2) with a straight
chain structure gives a C4 carboxylic acid. A is. [JEE-Mains (1-September_Shift-2)2021]
LiAlH4 Oxidation
A 
H O
 B   C4  Carboxylic acid
3
(A) CH3 –CH2 – COO –CH2 – CH2 – CH3 (B) CH3 –CH2 – CH2 – COO– CH2 – CH3
OH
(C) CH 3 – CH2 – CH – CH2 – O – C H = CH 2 (D) CH3 –CH2 – CH2 – O–CH = CH – CH2 – OH
OCH3
(i) NaCN
-
(ii) OH
A
(iii) Cyclohexanone Major Product
45. (iv) H 2, Ni
Br
The major product of the above reactions is : [JEE-Mains (24-Jun-Shift-1)2022]
46. Number of electrophilic centre in the given compound is [JEE-Mains (24-Jun-Shift-1)2022]

CH3
CH2CN
47. Hex-4-ene-2-ol on treatment with P C C gives ‘ A ‘. ‘A’ on reaction with sodium hypoiodite gives ‘B’,
which on further heating with soda lime gives ‘ C ‘. The compound ‘C ‘ is
(A) 2-pentene (B) proponaldehyde (C) 2-butene (D) 4 -inethylpent-2-ene
48. Which of the following ketone will NOT give enamine on treatment with Question: secondary amines?
[where t-Bu is C(CH3)3 ] [JEE-Mains (25-Jun-Shift-2)2022]
O
O O O
(A) C (B) C (C) C (D)
C 2 H5 C2 H5 C 2H 5 CH3 t -Bu t-Bu
49. Among the following structures, which will show the most stable enamineformation ?
(Where Me is- CH3) [JEE-Mains (26-Jun-Shift-1)2022]
COOH COOH
N N
COOH COOH
N N
(A) (B) (C) (D)
Me OMe Me MeO
Me Me
OMe OMe
50. Oxidation of toluene to benzaldehyde can be easily carried out with which of the Question: following
reagents? [JEE-Mains (26-Jun-Shift-2)2022]
+
(A) CrO3 /acetic acid, H3O (B) CrO3 /acetic anhydride, H3O+
+
(C) KMnO4HCl, H3O (D) CO / HCl, anhydrous AlCl3
51. The reagent, from the following, which converts benzoic acid to benzaldehyde in one step is
CHO
COOH
(A) LiAlH4 (B) KMnO4 (C) MnO (D) NaBH4
52. The final product ‘A’ in the following reaction sequence [JEE-Mains (26-Jun-Shift-2)2022]
95% H2SO4
CH3 CH2 C CH3 HCN ? A
Heat
O
CH3 OH
(A) CH3 CH C COOH (B) CH3 CH C CN (C) CH3 CH2 C COOH (D) CH3 CH C CONH2
CH3 CH3 CH3
53. Which of the following reactions will yield benzaldehyde as a product?

CH2OH
COOH
(i) SOCl 2, Quinoline
(A) (ii) H 2/Pd/BaSO4 (B) CrO 3 /H 2SO 4
O O
C OCH3 C OCH3
(C) (i) NaBH 4 (D) (i) CrO 3,(CH3CO)2 O
+
(ii) PCC (ii) H 3O , 
(A) B and C (B) C and D (C) A and D (D) A and C
54. L-isomer of a compound ‘ A’ (C4H8O4) gives a positive test with [Ag(NH3)2]+ .Treatment of ‘ A’ with
aceticanhydride yields triacetate derivative. Compound ‘ A ‘ produces an optically active compound
(B) and an optically inactive compound (C) on treatment with bromine water and HNO3 respectively.
Compound (A) is : [JEE-Mains (27-Jun-Shift-1)2022]
CHO CHO CHO CHO
HO H H OH H OH HO H
(A)HO H (B) HO H (C) H OH (D) H OH
CH2OH CH2OH CH2OH CH2OH

Statement I: Maltose has two -D-glucose units linked at C1 and C4 and is a reducing sugar.
Statement II: Maltose has two monosaccharides: -D-glucose and -D-glucose linked at C1 and C6 and
it is a non-reducing sugar.
In the light of the above statements, choose the correct answer from the options Question: given
below.
(A) Both Statement I and Statement II are true.
(B) Both Statement I and Statement II are false.
(C) Statement I is true but Statement II is false.
(D) Statement I is false but Statement II is true.
56. The correct structure of product ‘A’ formed in the following reaction,
O
NaOD - (Ph is -C 6H5)
PhCHO + Ph. CHO in D O A + Ph C O
2
OD OH OD OD
H H D D
(A) (B) (C) (D)
Ph H Ph H Ph H Ph D
57. Isobutyraldehyde on reaction with formaldehyde and K2CO3gives compound ‘ A’ prime. Compound ‘ A
‘reacts with KCN and yields compound ‘B’, which on hydrolysis gives a stable compound ‘C’. The
compound ‘C ‘is [JEE-Mains (28-Jun-Shift-2)2022]
CH3
(A) HO CH2 C CH COOH (B) HO CH 2CH 2 CH CH COOH

CH3 OH CH3 OH
HO H3C O
O
H3C
(C) H3C (D) O
H3C O
HO
58. In the given reaction [JEE-Mains (29-Jun-Shift-2)2022]
(i) K 2 Cr 2 O 7
HO 'X'
(ii) C 6 H 5 MgBr
(iii) H 2 O Major Product
+
(iv) H , heat
the number of sp2 hybridised carbon(s) in compound ‘X’ is
59. In the given reaction, [JEE-Mains (29-Jun-Shift-2)2022]
O
-
(i) OH
'P'
(ii) heat Major Product
The number of  electrons present in the product ‘P’ is
60. In the given reaction [JEE-Mains (25-July_Shift-1)2022]

O
H3C
C OEt
CH2 C CH3 O Et
A (Where Et is –C2H5)
O
The number of chiral carbon/s in product A is __________
61. What is the major prouct of the following reaction ? [JEE-Mains (25-July_Shift-2)2022]
-
H OH
H2 O
O
O O OH O O O
(A) H (B) H (C) H (D) H
62. The products formed in the following reaction, A and B are [JEE-Mains (26-July_Shift-1)2022]
O
+ -
[Ag(NH3) 2] OH NaBH4
A B
H CHO
O
H H OH H OH
OH
A= B= A= , B=
(A) , (B)
H CH2OH H CH2OH H CHO H CH2OH
O O
H OH H OH
A= B= A= , B=
(C) , (D)
H COOH H COOH H COOH H CH2OH

2 
1. Ph–CC– CH3 Hg
 /H
 A [JEE 2005]
O
Ph Ph O O
(A) (B) (C) Ph (D) Ph

CH3 OH
CH3
CH3 CH 3
COOH
CHO
CH3COONa
2. +X
MeO MeO
What is X ? [JEE 2005]

(A) CH3COOH (B) BrCH2,COOH (C) (CH3CO)2O (D) CHO—COOH
3. How will you convert butane-2-one to propanoic acid? [JEE 2005]

(A) Tollen reagent (B) Fehling solution (C) NaOH / I2/H+ (D) NaOH/NaI/H +
4. The smallest ketone and its next homologue are reacted with NH2OH to form oxime. [JEE 2005]
(A) Two different oximes are formed (B) Three different oximes are formed
(C) Two oximes are optically active (D) All oximes are optically active
5. Which ofthe following disaccharide will not reduce Tollen’s reagent ? [JEE 2005]
CHOH HOH2C CH2 OH

CHOH
2 2
O HO O H H
HO O OH
HO O H H
H OH H HO OH H
(A) H HO (B)
O H H O H
H
OH H OH H H OH
OH H (P)
(Q)
OH
 (i) O3 NaOH
6. H
,
 X (ii)  Y 
Zn / CH COOH 3
Identify (X) and (Y) [JEE 2005]
7. Which of the following reactats on reaction with conc. NaOH followed by acidification gives the following
lactone as the only product? [JEE 2006]
O
C
O
CH2
COOCH3 COOH CHO COOH

(A) (B) (C) (D)
COOH CHO CHO COOH
8. Cyclohexene on ozonolysis followed by reaction with zinc duct and water gives compoundE. Compound E on
further teratment with aqueous KOH yields compound F. Compound F is [JEE 2007]
CO2H
(A) CHO (B) CHO (C) COOH (D)
CO2H
9. Statement -1 : Glucouse gives a reddish- brown precipitate with Fehling’s solution. because [JEE 2007]
Statement -2 : Reaction of glucose with fehling’s solution gives CuO and gluconic acid.
(A) Statement -1 is True ; Statement -2 is True; statement-2 is a correct explanation for statement-1
(B) Statement -1 is True; Statement -2 is True; statement-2 is NOT a corrcect explanation for statement -1
(C) Statement -1 is True, Statement -2 is False.
(D) Statement -1 is Fals, Statement -2 is True.
10. Match the compounds/ion in column l with their properties / reaction in Cloumn ll. Indicate your answer by
darkening the appropriate bubbles of the 4  4 matrix given in the ORS. [JEE 2007]
Column l
(A) C6H5CHO
(B) CH3C  CH
(C) CN–
(D) l–
Column ll
(P) give precipitate with 2,4-
dinitrophenylhydrazine
(Q) gives precipitate with AgNO3
(R) is a nucleophile
(S) is involved in cyanohydrin formation
Column II
(P) sodium fusion extract of the compound
gives Prussian blue colour with FeSO4
(Q) gives positive FeCl3 test
(R) gives white precipitate with AgNO3
(S) reacts with aldehydes to form the corre sponding hydrazone de rivative
Paragraph for Question No. 11 to 13

A tertiary acohol H upon acid catalysed dehydration gives a product l. Ozonolysis of l leads to compounds J and
K compound J upon reaction with KOH gives benzyl alcohol and a compound L, whereas K on reaction with
KOH gives only M. [JEE 2008]
O
H3C Ph
M=
Ph H
11. Compound H is formed by the reaction of

O O
(A) + PhMgBr (B) + PhCH2MgBr

Ph CH 3 Ph CH 3
O O Me
(C) + PhCH2MgBr (D) +

Ph H Ph H Ph MgBr
12. The structure of compound l is
H3C Ph CH3 H 3C
Ph CH3 Ph CH3
(A) (B) (C) (D)

H Ph H H CH2Ph H
Ph Ph
13. The structures of compounds J,K and L, respectively are

(A)PhCOCH3,PhCH2COCH 3 and PhCH2COO– K+
(B) PhCHO,PhCH2CHO and PhCOO–K+
(C) PhCOCH3, PhCH2CHO and CH3COO–K+
(D) PhCHO,PhCOCH3 and PhCOO–K+
Paragraph for Question Nos. 14 to 16

A carbonyl compound P, which gives positive iodoform test, undergoes reaction with MeMgBr followed by
dehydration to give an olefin Q. Ozonolysis of Q leads to a dicarbonyl compound R which undergoes intramolecular
aldol reaction to give predominantly S. [JEE 2009]
1. MeMgBr 1. O 1. OH 
P  Q 
3
 R  S
2. H , H 2 O 2. Zn,H2O 2. 
3. H 2SO 4 , 
14. The structure of the carbonyl compound P is

O
Me
(A) O Me (B) (C) (D)

O Me O Et
Et
15. The structures of the products Q and R, respectively are

O O
Me H H
(A) , COMe (B) , CHO
Me Me Me Me
Me Me Me Me
O O
Me
H CH3
(C) , CHO (D) , CHO
Me Et Me
Me Et Me Et
16. The structure of the product S is :

O
O
O
Me
(A) (B) (C) (D)
O
Me Me Me
Me Me
Paragraph of Question Nos. 17 to 19
Two aliphatic aldehydes P and Q react in the presence of aqueous K2CO3 to give compound R which upon
treatment with HCN provides compound S. On acidification and heating. S gives the product shown below
H3C OH
H3C
[JEE 2010]
O O
17. The compounds P and Q respectively are -

CH3
CH3
H3C H H H
CH
CH H
H and C C
(A) (B) H3C C and
H3C C O O
O
O
H3C H CH2 H H
H3C
H
CH2 CH C
H3C C C
(C) H and (D) and
CH C O O O
CH3
O
CH3
18. The compound R is

O
O
HC C
(A) C H (B) H3C C
H3 C C H
H 2C H3C
OH CH
H3C OH
O O
CH 3 CH3
CH C CH CH
(C) HC
3 CH H (D) H3 C CH H
CH2 CH
OH OH
H3 C
19. The compound S is

O O
CH3
CH C H3C C
(A) H3C CH H (B) C H
H3C
H2C H2C
CN CN
CH 3 CN CN
CH CH
CH
(C) H3 C CH OH (D) H3 C OH
C
H2C H3 C
OH CH 2
OH
20. In the scheme given below the total number of intramolecular aldol condensation products formed from Y is
1
.O 3
 1. NaOH ( aq )
Y    [JEE 2010]
2. Zn , H 2 O 2. heat
21. Among the following the number of reaction(s) that produce(s) benzaldehyde is [JEE Adv. 2015]
I. II.
III. IV.
22. The major product of the following reaction is [JEE Adv. 2015]
(A) (B) (C) (D)
23. Positive Tollen's test is observed for

[JEE Adv. 2016]
H O CHO OH
Ph O
(A) H (B) (C) Ph (D)
H O Ph Ph
H
24. The major product of the following reaction sequence is [JEE Adv. 2016]
O
(i) HCHO (excess)/NaOH, heat
(ii) HCHO/H+(catalytic amount)
O OH
O O O O OH O O
HO
(A) (B) (C) (D)
OH
Paragraph "A"
An organic acid P (C11H12O2) can easily be oxidized to a dibasic acid which reacts with ethyleneglycol to produce
a polymer dacron. Upon ozonolysis, P gives an aliphatic ketone as one of the products.
P undergoes the following reaction sequences to furnish R via Q. The compound P also undergoes another set of
reactions to produce S.
(1) H2/Pd-C
(1) H2/Pd-C (1) HCl
(3) Br2/NaOH (2) SOCl2 (2) Mg/Et2O
S P Q R
(3) MeMgBr, CdCl2 (3) CO2 (dry ice)
(5) H2/Pd-C (4) NaBH 4 (4) H3O+
(There are two questions based on PARAGRAPH "A", the question given below is one of them)
25. The compound R is:- [JEE Adv. 2018]

HO2C
(A) CO2H (B)
CO2H CO2H
(C) (D)
26. The compound S is [JEE Adv. 2018]
NH 2 H
N
(A) (B) (C) (D)
NH 2 HN
27. Choose the correct option(s) for the following reaction sequence [JEE Adv. 2019]
2+
CHO (i) H g , dil. H2SO 4
(i) SOCl 2
(ii) AgNO 3, NH4OH Zn-Hg
pyridine Conc. HCl
(iii) Zn-Hg, conc. HCl Q R S
(ii) AlCl 3
MeO
Consider Q, R and S as major products.
CO2H
(A) (B)
MeO MeO MeO MeO
O O
R S Q R
OH
CO2H
(C) (D)
MeO MeO
MeO MeO
O
R Q R
S
28. Answer is following by appropriately matching the lists based on the information given in the paragraph
List - I includes starting materials and reagents of selected chemical reactions. List - II gives structures of
compounds that may be formed as intermediate products and/or final products from the reactions of List-I
[JEE Adv. 2019]
List-I List-II
i) DIBAL-H
CN ii) dil. HCl CHO
(I) (P)
O iii) NaBH4
iv) conc.H2SO4 CO2H
O
i) O3
ii) Zn, H2O OH
(II) iii) NaBH4 (Q)
OH
CO2H iv) conc.H2SO4
i) KCN
+
ii) H3O , 
Cl
(III) iii) LiAlH4 (R) O
CO2CH3 iv) conc.H2SO4
CO2Me OH
i) LiAlH4
(IV) ii) conc.H2SO4 (S)
CO2Me
CO2H
CO2H
(T)
CO2H
(U) O
Which of the following options has correct combination considering List-I and List-II ?
(A) (III), (T), (U) (B) (IV), (Q), (U) (C) (III), (S), (R) (D) (IV), (Q), (R)
29. Total number of hydroxyl groups present in a molecule of the major product P is ________.
(i) H2, Pd-BaSO4, quinoline

P [IIT Adv. 2019]
(ii) dil. KMnO4(excess), 273 K
30. Total number of isomers, considering both structural and stereoisomers, of cyclic ethers with the molecular
formula C4H8O is _______. [IIT Adv. 2019]
31. Choose the correct option(s) for the following reaction sequence : [IIT Adv. 2019]
2+
(i) Hg , dil. H2SO4 (i) SOCl2
CHO (ii) AgNO3, NH4OH pyridine Zn-Hg,
Q R S
(iii) Zn-Hg, conc. HCl (ii) AlCl3 Conc. HCl
MeO
Consider Q, R and S as major products
CO2H
(A)
MeO MeO
O
(Q) (R)
OH
CO2H
(B)
MeO MeO
(Q) (S)
(C)
MeO MeO
O
(R) (S)
(D)
MeO MeO
O
(R) (S)
32. Consider the following transformations of a compound P. [IIT Adv. 2020]
Choose the correct options(s).
(A) P is (B) X is Pd-C/quinoline/H2
(C) P is (D) R is
1. C 2. B 3. D 4. B 5. D 6. C 7. D
8. B 9. B 10. A 11. A 12. B 13. B 14. D
15. A 16. D 17. B 18. B 19. 3 20. A 21. 7
22. C 23. A 24. B 25. B 26. B 27. 5 28. A
29. 3 30. D 31. D 32. D 33. A 34. D 35. A
36. B 37. B 38. B 39. B 40. C 41. D 42. B
43. 2 44. B 45. D 46. (3) 47. C 48. C 49. C
50. B 51. C 52. A 53. C 54. A 55. C 56. A
57. C 58. 8 59. 4 60. 2 61. B 62. C
1. A 2. C 3. C 4. B
5. (B) In structure (P) both the rings are present in acetyl form therefore it will not hydrolyse in solution that why
Tollen’s solution connot react with this.
In structure (Q) one ring present in the form of hemiacetal. This will hydrolysed in solution it can reduce Tollen’s
solution.
6. (X) (Y) CH3— C —(CH2)4—CH=O 7. C 8. A 9. C

CH3
10. A  P,Q,S; B  Q,R ; C  Q,R,S ; D  Q,R
11. B 12. A 13. D 14. B 15. A 16. B 17. B
18. A 19. D 20. 1 21. A, B,C,D 22. A 23. ABC
24. A 25. A 26. B 27. B,C 28. D 29. 6.00
30. 10.00 31. AC 32. BC

Carboxylic Acid | JEE Main
Q.1 Which one of the following does not have sp2 hybridized carbon ? [AIEEE-2004]
(A) Acetone (B) Acetic acid (C) Acetonitrile (D) Acetamide
Q.2 Consider the acidity of the carboxylic acids : [AIEEE-2004]

(a) PhCOOH (b) o – NO2C6H4COOH
(c) p – NO2C6H4COOH (d) m – NO2C6H4COOH
Which of the following order is correct ?
(A) a > b > c > d (B) b > d > c > a (C) b > d > a > c (D) b > c > d > a
Q.3 Rate of the reaction : [AIEEE-2004]
O O
R–C + Nu–  R – C + Z–
Z Nu
is fastest when Z is :
(A) OCOCH3 (B) NH2 (C) OC2H5 (D) Cl
Q.4 On mixing ethyl acetate with aqueous sodium chloride, the composition of the resultant solution is :
(A) CH3Cl + C2H5COONa (B) CH3COONa + C2H5OH [AIEEE-2004]
(C) CH3COCl + C2H5OH + NaOH (D) CH3COOC2H5 + NaCl
Q.5 Which one of the following is reduced with zinc and hydrochloric acid to give the corresponding hydrocarbon :
[AIEEE-2004]
(A) Butan-2-one (B) Acetic acid (C) Acetamide (D) Ethyl acetate
Q.6 The compound formed in the positive test for nitrogen with the Lassaigne solution of an organic compound is -
[AIEEE-2004]
(A) Fe4[Fe(CN)6]3 (B) Na3[Fe(CN)6] (C) Fe(CN)3 (D) Na4[Fe(CN)5NOS]
Q.7 Which one of the following methods is neither meant for the synthesis nor for separation of amines ?
[AIEEE-2005]
(A) Hofmann method (B) Hinsberg method (C) Curtius reaction (D) Wurtz reaction
Q.8 Reaction of cyclohexanone with dimethylamine in the presence of catalytic amount of an acid forms a compound
if water during the reaction is continuously removed. The compound formed is generally known as –
[AIEEE-2005]
(A) an enamine (B) a Schiff’s base (C) an amine (D)an imine
Q.9 In the chemical reaction, CH3CH2NH2 + CHCl3 + 3KOH  (A) + (B) + 3H2O, the compounds (A) and (B) are
respectively - [AIEEE-2007]
(A) C2H5CN and 3KCl (B) CH3CH2CONH2 and 3KCl
(C) C2H5NC and K2CO3 (D) C2H5NC and 3KCl
Q.10 The compound formed as a result of oxidation of ethyl benzene by KMnO4 is – [AIEEE-2007]
(A) benzophenone (B) acetophenone (C) benzoic acid (D) benzyl alcohol
Q.11 A liquid was mixed with ethanol and a drop of concentrated H2SO4 was added. A compound with a fruity smell
was formed. The liquid was : [AIEEE-2009]
(A) CH3OH (B) HCHO (C) CH3COCH3 (D) CH3COOH
Q.12 An organic compound A upon reacting and NH3 gives B. On heating B gives C. in presence of KOH reacts is
with Br2 to given CH3CH2NH2 A is [JEE Main 2013]
(A) CH3– CH –COOH (B) CH 3CH2COOH

CH3
(C) CH3COOH (D) CH3CH2CH2COOH
Q.13 The major product obtained in the following reaction is: [JEE Main 2017]
O
O
DIBAL-H
COOH
OH OH
CHO CHO
(A) CHO (B) (C) (D) CHO
COOH CHO
CHO COOH
Q.14 Sodium salt of an organic acid 'X' produces effervescence with conc. H2SO4. 'X' reacts with the acidified
aqueous CaCl2 solution to give a white precipitate which decolourises acidic solution of KMnO4. 'X' is:
[JEE Main 2017]
(A) HCOONa (B) CH3COONa (C) Na 2C2O4 (D) C6H5COONa
Q.15 Which of the following compounds will be suitable for Kjeldahl's method of nitrogen estimation ?
[JEE Main 2018]
+
N2Cl
–
NH2 NO2
(A) (B) (C) (D)
N
16. The increasing order of basicity of the following compounds is : [JEE (Mains) 2018]
NH2 NH
(a) (b)
NH 2
(c) (d) NHCH3
NH
(A) (b) < (a) < (c) < (d) (B) (b) < (a) < (d) < (c) (C) (d) < (b) < (a) < (c) (D) (a) < (b) < (c) < (d)
17. Which dicarboxylic acid in presence of a dehydrating agent is least reactive to give an anhydride ?
[2019 Mains]
CO2H CH2 COOH C

CH2 COOH CH2 OH
(A) (B) (C) (D)
CH2 COOH COOH CH2 OH
CO2H
CH2 C
18. The major product of the following reaction is [2019 Mains]
OH
CH2OH
H2SO4 (cat.)
CHCl3
CO2Et
O O OH OH
(A) (B) (C) (D)

OEt
O
CO2Et COOH
O O
19. The major product of the following reaction is [2019 Mains]
O Cl
(i) AlCl3, heat

O +
(ii) H2O
O CO2H
Cl
(A) (B)
Cl O
O
O Cl O
(C) (D)
COOH Cl
O
20. The increasing order of the reactivity of the following with LiAlH4 is [2019 Mains]
O O O O O
(A) (B) (C) (D)

C2H5 NH2 C2H5 OCH3 C2H5 Cl C2H5 O C2H5
(A) (A) < (B) < (D) < (C) (B) (A) < (B) < (C) < (D)
(C) (B) < (A) < (D) < (C) (D) (B) < (A) < (C) < (D)
21. The major product obtained in the following reaction is [2019 Mains]
CO2Et
O
O
O O O O
(A) (B) (C) (D)
CO2Et CO2Et
CO2Et CO2Et
22. The decreasing order of case of alkaline hydrolysis for the following esters is [2019 Mains]
COOC2H5 Cl COOC2H5 O2N COOC2H5 CH3O COOC2H5
(I) (II) (III) (IV)

(A) III > II > IV > I (B) III > II > I > IV (C) II > III > I > IV (D) IV > II > III > I
23. The compound A and B in the following reaction are, respectively [2019 Mains]
HCHO  HCl AgCN


 A  B
(A) A = Benzyl alcohol, B = Benzyl isocyanide (B) A = Benzyl alcohol, B = Benzyl cyanide
(C) A = Benzyl chloride, B = Benzyl isocyanide (D) A = Benzyl chloride, B = Benzyl cyanide
24. The major product of following reaction is [2019 Mains]

(i) AIH(i.Bu )
R  C  N 
(ii) H O
2

2
(A) RCHO (B) RCONH2 (C) RCOOH (D) RCH2NH2
25. The major product of the following reaction is [JEE-Main 2019]

OH
Ethyle formate (1 equiv.)
CH 3 CH CH 2CH 2NH 2 
Triethylamine

OH
(A) CH3 CH CH2CH2NHCHO (B) CH3 = CH––CH2NH2
O
OH
(C) CH3 –– CH –– CH = CH2 (D) O H
CH3CHCH 2CH2NH2
26. Ethylamine (C2H5NH2) can be obtained from N-ethylphthalimide on treatment with
[JEE-Main 2019]
(A) NaBH4 (B) NH2NH2 (C) H2O (D) CaH2
27. Hinsberg’s reagent is [JEE-Main 2019]

(A) SOCl2 (B) C6H5COCl (C) C6H5SO2Cl (D) (COCl)2
28. Which of the following amines can be prepared by Gabriel phthalimide reaction ?
[JEE-Main 2019]
(A) n-butylamine (B) triethylamine (C) t-butylamine (D) neo-pentylamine
29. A compound ‘X’ on treatment with Br2/NaOH, provided C3H9N, which gives positive carbylamine test. Compound
‘X’ is [JEE-Main 2019]
(A) CH3COCH 2NHCH3 (B) CH 3CH2CH2CONH2
(C) CH 3CON(CH3) 2 (D) CH 3CH2COCH 2NH2
30. The major product of the following reaction is [JEE-Main 2019]
O
CH3N NaBH4
OH O
(A) CH3N (B) CH3NH
OH OH
(C) CH3NH (D) CH3N
31. The major product formed in the reaction given below will be [JEE-Main 2019]
NH2
NaNO2
Aq.HCl,0-5°C
NO2 OH
(A) NO 2 (B) OH (C) (D)
32. The major product obtained in the following reaction is [JEE-Main 2019]
OH
(CH3CO)2 O/pyridine (1eqv.)

room temperature
NH2
COCH3
OH OH OCOCH3
(A) (B) (C) (D)

NH2 NHCOCH3 NHCOCH3 NH2
33. The major products of the following reaction are
OH
(1) CHCl3/aq.NaOH
(2) HCHO, NaOH (conc.)
(3) H3 O+
Cl
OH OH
COOH COOH
(A) and methanol (B) and methanol
Cl OH
OH OH
OH OH
(C) and formic acid (D) and formic acid
OH Cl
34. Major products of the following reaction are [JEE-MAIN 2019]
CHO
(i) 50% NaOH

+HCHO (ii) H3O
+
COOH
(A) CH3OH and HCO2H (B) CH3OH and
CH2OH
CH2OH COOH
(C) HCOOH and (D) and

35. What is ‘X’ in the given reaction ? [JEE-Mains (25-Feb_Shift -2)2021]
CH2 OH
210 0 C x
+ oxalic acid
(major product)
CH2 OH
CH 2 CH—OH CH 2 OH CHO
CH 2 CH 2 CHO
CHO
(1) (2) (3) (4)
CN
COOH
H2 O H2 O
36. “A”
+ +
H H,
(Major Product)

Consider the above chemical reaction and identity product “A” :
(A) (B) (C) (D)
37. Compound A is converted to B on reaction with CHCl3 and KOH. The compound B is toxic and can be
decomposed by C. A, B and C respectively are : [JEE-Mains (20-July_Shift -1)2021]
(A) secondary amine, nitrile compound, conc. NaOH
(B) primary amine, isonitrile compound, conc. HCl
(C) secondary amine, isonitrile compound, conc. NaOH
(D) primary amine, nitrile compound, conc. HCl
O
O O O O H
R N
O R R
38. (A) R Cl (B) R (C) R O (D) H
The correct order of their reactivity towards hydrolysis at room temperature is :

(A) (D)> (B) > (A) >(C) (B) (D) > (A) > (B) >(C)
(C) (A) > (B) > (C) >(D) (D)(A) > (C) > (B) >(D)
O
O
O
Maleic anhydride
Maleic anhydride can be prepared by :
(A) Treating cis-but-2-enedioic acid with alcohol and acid
(B) Heating cis-but-2-enedioic acid
(C) Treating trans-but-2-enedioic acid with alcohol and acid
(D)Heating trans-but-2-enedioic acid
40. The major product formed in the following reaction is : [JEE-Mains (26-August_Shift-1)2021]
COOH
SOCl2,CH 3OH
NH2 Major product
N
H
Cl CO2Me COCl
(A) NH2 (B) NH2

N N
H H
CO2CH 3 CO2CH 3
NH 2·HCl NH2·HCl
(C) N (D) N
H·HCl
H
41. The major product of the following reaction is : [JEE-Mains (27-August_Shift-1)2021]

CH3 O (i) alcoholic NH 3
(ii) NaOH,Br 2
CH3 – CH– CH 2– CH 2–C–Cl Major Product
(iii) NaNO 2, HCl
(iv) H 2O
Br
CH3 – CH– CH2– CH 2–C–Cl
CH3 – CH– CH– CH 2OH
(A) (B)
CH 3
CH 3
CH3 – CH– CH2– CH 2–CH 2OH CH3 – CH–CH 2–CH 2OH

(C) (D)
CH 3 CH3
42. The structure of product C, formed by the following sequence of reactions is :

Benzene KCN
CH3COOH  SOCl2  A 
AlCl
 B 
–
OH
C [JEE-Mains (31-August_Shift-1)2021]
3
H COOH NC OH O
CH2–C H2CN C
CH3 CH3 CH 3
(A) (B) (C) (D)
CN
43. Which one of the following gives the most stable Diazonium salt?
[JEE-Mains (1-September_Shift-2)2021]
NHCH3 NH 2
CH 3
(A) CH C CH 3 (B) CH3–CH2–CH2–NH2 (C) (D)

3
CH3
H
44. Two statements are given belwo: [JEE-Mains (24-Jun-Shift-1)2022]

Statement I : The melting point of monocarboxylic acid with even number of carbon atoms is higher
than that of with odd number of carbon atoms acid immediately below and above it in the series.
Statement II :The solubility of monocarboxylic acids in water decreases with increase in molarmass.
45. Given below are two statements: one is labelled as Assertion A and the other is labelled as Reason R.
Assertion A : A mixture contains benzoic acid and napthalene. The pure benzoic acid can be separated
out by the use of benzene. [JEE-Mains (25-Jun-Shift-2)2022]
Reason R : Benzoic acid is soluble in hot water.
below.
(A) Both A and R are true and R is the correct explanation of A.
(B) Both A and R are true but R is NOT the correct explanation of A.
(C) A is true but R is false.
(D) A is false but R is true.
46. Decarboxylation of all six possible forms of diaminobenzoic acids C6H3(NH2)2 COOH yields three products
A,B and C. Three acids give a product ‘A’, two acids gives a product ‘B’ and one acid give a product ‘C’.
The melting Question: point of product ‘C’ is [JEE-Mains (27-Jun-Shift-2)2022]
(A) 63ºC (B) 90ºC (C) 104ºC (D) 142ºC

Statement I : The esterification of carboxylic acid with an alcohol is a nucleophilic acyl substitution.
Statement II : Electron withdrawing groups in the carboxylic acid will increase the rate of esterification
reaction.
48. Which one of the following reactions does not represent correct combination of substrate and product
under the given conditions ? [JEE-Mains (25-July_Shift-1)2022]
O O
Cl H2 H
(A) Pd. BaSO 4
O
CN
(i) DIBAL-H H
(B) (ii) H 2O
O
CO2C2H5
(i) ALH(iso BU) 2 H
(C)
(ii) H 2O
OH H
(i) Na 2Cr 2O 7
(D)
(ii) H 2SO4, H 2O
1. The correct IUPAC name of C6H5COCl is [IIT 2006]
(A) Benzoyl chloride (B) Benzene chloro ketone
(C) Benzene carbonyl chloride (D) Chloro phenyl ketone
2. Which of the following reactants on reaction with conc. NaOH followed by acidification gives the following
lactone as the only product ? [IIT 2006]
(A) (B) (C) (D)
3. Match the compounds in Column I with their characteristic test(s)/reaction(s) given in Column II. Indicate your
answer by darkening the appropriate bubbles of the 4 × 4 matrix given in the ORS. [IIT 2008]
Column I Column II
+ -
(A) H2N – NH3Cl (P) sodium fusion extract of the compound gives Prussian blue colour
with FeSO4
+ -
NH3I
(B) HO (Q) gives positive FeCl3 test
COOH
+ -
(C) HO NH3Cl (R) gives white precipitate with AgNO3
+ -
(D) O2N NH – NH3Br (S) reacts with aldehydes to form the corresponding hydrazone derivative
NO2
4. Match each of the compounds given in Column I with the reaction(s), that they can undergo, given in Column II.
Column I Column I [IIT 2009]
Br
(A) (P) Nucleophilic substitution
O
(B) OH (Q) Elimination
CHO
(C) (R) Nucleophilic addition
OH
Br
(D) (S) Esterification with acetic anhydride
NO2
(T) Dehydrogenation
O
C
(i) KOH
NH
C (ii) Br CH2Cl
O
O O
C C
(A) N CH2 Br (B) N CH2Cl
C C
O O
O O
C C
(C) N (D) N
C C
O – CH2 Br O CH2Cl
6. Among the following compounds, the most acidic is [IIT 2011]

(A) p-nitrophenol (B) p-hydroxybenzoic acid
(C) o-hydroxybenzoic acid (D) p-toluic acid
7. The carboxy functional group (–COOH) is present in [JEE Adv. 2012]

(A) picric acid (B) barbituric acid (C) ascorbic acid (D) aspirin
8. The compound that undergoes decarboxylation most readily under mild condition in [JEE Adv. 2012]
COOH COOH COOH CH 2COOH
CH2COOH O COOH O
(A) (B) (C) (D)
9. After completion of the reaction (I and II), the organic compound(s) in the reaction mxitures is (are)
O
Br2(1.0 mol)
Reaction I : H3C CH 3 aqueous NaOH
(1.0 mol)
O [JEE Adv. 2013]

Br2(1.0 mol)
Reaction II : H3C CH 3 CH3COOH
(1.0 mol)
O O O
H3C CH2Br H3C CBr3 Br3C CBr3
Q R
P
O O
BrH2C CH2Br H3C ONa CHBr3

S T U
(A) Reaction I : P and Reaction II : P
(B) Reaction I : U, acetone and Reaction II : Q acetone
(C) Reaction I : T, U, acetone and Reaction II : P
(D) Reaction I : R, acetone and Reaction II : S, acetone
Pargraphs for Questions 10 and 11
P and Q are isomers of dicarboxylic acid C2H4O4. Both decolorize Br2/H2O. On heating, P forms the cyclic
anhdride
Upon treatment with dilute alkaline KMnO4, P as well as Q could produce one or more than one from S, T and U.
COOH COOH COOH
H OH H OH OH H
H OH HO H H OH
COOH COOH COOH

S T U
10. Compounds formed from P and Q are, respectively [JEE Adv. 2013]
(A) Optically active S and Optically active pair (T, U)
(B) Optically inactive S and optically inactive pair (T, U)
(C) Optically active pair (T, U) and optically active S
(D) Optically inactive pair (T, U) and optically inactive S
11. In the following reation sequances V and W are. respectively [JEE Adv. 2013]
H2/Nl AlCl3(andhydrous) 1. Zn – Hg /HCl

Q V +V W
2. H3PO4
O CH2OH
and
O and
(A) (B)
O CH 2OH W
V O V
W
O
HOH2C
O and and
(C) (D) CH2OH CH2OH
V
W
V W
12. In the reaction shown, below, the major product(s) formed is/are : [JEE Adv. 2014]
H
N CH3
O + CH3COOH
(A) (B) + CH3COOH
NH2
O
H
N CH 3
O + H2O
(C) H (D)
N CH 3
O O
13. Consider all possible isomeric ketones, including stereoisomers of MW = 100. All these isomers are independently
reacted with NaBH4 (NOTE : stereoisomers are also reacted separately). The total number of ketones that give
a racemic product(s) is/are. [JEE Adv. 2014]
14. The product(s) of the following reaction sequence is(are): [JEE Adv. 2016]
NH2
(i) Acetic anhydride/pyridine
(ii) KBrO3/HBr
+
(iii) H3O , heat
(iv) NaNO2/HCl, 273-278 K
(v) Cu/HBr
Br Br
Br Br Br
Br
Br Br
(A) (B) (C) (D)
Br Br Br
15. Compounds P and R upon ozonolysis produce Q and S, respectively. The molecular formula of Q and S is C8H8O.
Q undergoes cannizzaro reaction but not haloform reaction, whereas S undergoes haloform reaction but not
cannizzaro reaction. [JEE Adv. 2017]
 3
i O / CH Cl
(i) P 
iiZn / H2O 
2 2
Q
(C 8H8O)
i O3 / CH2Cl2
(ii) R 
iiZn / H2O S
(C 8H8O)
The option(s) with suitable combination of P and R, respectively, is(are)
(A) H3C and H3C

CH3
(B) H3C and

CH3
H3C
CH3
—CH3
(C) and
CH3
H3C
H3C
CH3
CH3 CH3
(D) and
CH3
H3C H3C
Columns 1,2 and 3 contain starting materials, reaction conditions, and type of reactions, respectively.
[JEE Adv. 2017]
Column 1 Column 2 Column 3
(I) Toluene (i) NaOH/Br2 (P) Condensation
(II) Acetophenone (ii) Br2/hv (Q) Carboxylation
(III) Benzaldehyde (iii) (CH3CO)2O/CH.COOK (R) Substitution
(IV) Phenol (iv) NaOH/CO2 (S) Haloform
16. The only CORRECT combination in which the reaction proceeds through radical mechanism is
(A) (IV) (i) (Q) (B) (III) (ii) (P) (C) (II) (iii) (R) (D) (I) (ii) (R)
17. For the synthesis of benzoic acid, the only CORRECT combination is
(A) (II) (i) (S) (B) (I) (iv) (Q) (C) (IV) (ii) (P) (D) (III) (iv) (R)
18. The only CORRECT combination that gives two different carboxylic acids is
(A) (IV) (iii) (Q) (B) (II) (iv) (R) (C) (I) (i) (S) (D) (III) (iii) (P)
19. Aniline reacts with mixed acid (cone. HNO3 and cone. H2SO4) at 288 K to give P (51%), Q (47%) and R (2%).
The major product(s) the following reaction sequence is (are) : [JEE Adv. 2018]
(1) Ac2O, pyridine (1) Sn/HCl
(2) Br2, CH3CO2H (2) Br2/H2O (excess)
R + S major product(s)
(3) H3O (3) NaNO2, HCl/273-278K
(4) NaNO2, HCl/273-278K (4) H3PO2
Br
Br Br Br
Br Br
(A) (B) (C) (D)
Br Br
Br Br Br Br Br
Br Br
Paragraph "X"
Treatment of benzene with CO/HCl in the presence of anhydrous AlCl3/CuCl followed by reaction
with Ac2O/NaOAc gives compound X as the major product. Compound X upon reaction with Br2/Na2CO3,
followed by heating at 473 K with moist KOH furnishes Y as the major product. Reaction
of X with H2/Pd-C, followed by H3PO4 treatment gives Z as the major product. (There are two questions based
on PARAGRAPH "X", the question given below is one of them) [JEE Adv. 2018]
20. The compound Y is :–
OH
COBr Br
(A) (B)
HO O
Br
COBr
(C) (D)
Br
21. The compound Z is :-

OH
(A) (B) (C) (D)
O O O
22. The desired product X can be prepared by reacting the major product of the reactions in LIST-I with one or more
appropriate reagents in LIST-II.
(given, order of migratory aptitude: aryl > alkyl > hydrogen)
O
OH
Ph
Ph [JEE Adv. 2018]
Me
Page 183
LIST-I LIST-II
Ph
HO
P. Ph 1. I2, NaOH
Me
OH + H2SO4
Me
Ph
H2N
Q. Ph 2. [Ag(NH3) 2]OH
Me
OH + HNO2
Me
Ph
HO
R. Me 3. Fehling solution
Ph
OH + H2SO4
Me
Ph
Br
S. Ph 4. HCHO, NaOH
H
OH + AgNO3
Me
5. NaOBr
The correct option is
(A) P  1; Q  2, 3; R  1, 4; S  2, 4 (B) P  1, 5; Q  3, 4; R  4, 5; S  3
(C) P  1, 5; Q  3, 4; R  5; S  2, 4 (D) P  1, 5; Q  2, 3; R  1, 5; S  2, 3
23. Schemes 1 and 2 describe the conversion of P to Q and R to S, respectively. Scheme 3 describes the synthesis
of T from Q and S. The total number of Br atoms in a molecule of T is
NH2
(i) Br2(excess), H2O
(ii) NaNO2, HCl, 273 K
(iii) CuCN/KCN
Scheme 1 : Q
(iv) H3O+, D
(major)
(v) SoCl2, pyridine
P
(i) Oleum
Scheme 2 : +
S
(iii) H
(major) [JEE(Advanced)-2019]
(iv) Br2, CS 2, 273 K
R
(i) NaHO
Scheme 3 : (ii) Q
T
(major)
24. In the following reaction, compound Q is obtained from compound P via an ionic intermediate.
[JEE(Advanced)-2020]
What is the degree of unsaturation of Q ?

1. C 2. D 3. D 4. D 5. A 6. A 7. D
8. A 9. D 10. C 11. D 12. B 13. D 14. C
15. B 16. B 17. B 18. D 19. D 20. A 21. B
22. B 23. C 24. A 25. A 26. B 27. C 28. A
29. B 30. C 31. B 32. B 33. D 34. C 35. 1
36. C 37. B 38. C 39. B 40. D 41. D 42. C
43. D 44. A 45. D 46. D 47. A 48. D

1. C 2. C 3. A–RS, B–PQ, C–PQR, D–PS
4. A–PQT, B–PST, C–RS, D–P 5. A 6. C 7. D 8. B
9. A 10. B 11. A 12. A 13. 4 14. BC 15. B, C
16. D 17. A 18. D 19. D 20. C 21. A 22. D
23. 4.00 24. 18

Biomolecule & Polymers | JEE Main
1. In both DNA and RNA, heterocylic base and phosphate ester linkages are at – [AIEEE-2005]
(A) C2' and C5' respectively of the sugar molecule
(B) C5' and C2' respectively of the sugar molecule
(C) C5' and C1' respectively of the sugar molecule
(D) C3' and C5' respectively of the sugar molecule
2. Which of the following is a polyamide ? [AIEEE-2005]

(A) Nylon-66 (B) Teflon (C) Bakelite (D) Terylene
3. Which of the following is fully fluorinated polymer- [AIEEE-2005]

(A) Teflon (B) Neoprene (C) PVC (D) Thiokol
4. The pyrimidine bases present in DNA are – [AIEEE 2006]

(A) cytosine and guanine (B) cytosine and thymine
(C) cytosine and uracil (D) cytosine and adenine
5. The term anomers of glucose refers to – [AIEEE 2006]

(A) a mixture of (D)-glucose and (L)-glucose
(B) enantiomers of glucose
(C isomers of glucose that differ in configuration at carbon one (C-1)
(D) isomers of glucose that differ in configurations at carbons one and four (C-1 and C-4)
6. The secondary structure of a protein refers to– [AIEEE 2007]

(A) -helical backbone
(B) hydrophobic interactions
(C) sequence of -amino acids
(D) fixed configuration of the polypeptide backbone
7. -D-(+)-glucose and -D-(+)-glucose are [AIEEE 2008]

(A) epimers (B) anomers (C) enantiomers (D) conformers
8. Bakelite is obtained from phenol by reacting with [AIEEE 2008]

(A) CH3CHO (B) CH3COCH3 (C) HCHO (D) (CH2OH)2
9. Buna-N synthetic rubber is a copolymer of - [AIEEE 2009]

Cl
(A) H2C = CH – C = CH2 and H2C = CH– CH = CH2
(B) H2C=CH – CH = CH2 and H5C6 – CH = CH2
(C)H2C = CH – CN and H2C = CH – CH = CH2
(D) H2C = CH – CN and H2C = CH – C = CH2
CH3
10. The two functional groups present in a typical carbohydrate are : [AIEEE 2009]
(A) – OH and –COOH (B)– CHO and –COOH(C) > C = O and –OH (D) – OH and –CHO
11. Which amino acid is chiral ? [AIEEE-2009]
(A) Alanine (B) Valine (C) Prolline (D) Histidine
12. Biuret test is not given by - [AIEEE 2010]

(A) proteins (B) carbohydrates (C) polypeptides (D) urea
13. The presence or absence of hydroxy group on which carbon atom of sugar differentiates RNA and
DNA ? [AIEEE 2011]
(A) 1st (B) 2nd (C) 3er (D) 4th
14. Which one of the following statements is correct ? [JEE Main 2012]
(A) All amino acids are optically active
(B) All amino acids except glycine are optically active
(C) All amino acids except glutamic acid are optically active
(D) All amino acids except lysine are optically active
15. Which of the following compounds can be detected by Molisch’s test ? [JEE Main 2012]
(A) Sugars (B) Amines
(C) Primary alcohols (D) Nitro compounds
16. The species which can best serve as an initiator for the cationic polymerization is [JEE Main 2012]
(A) HNO3 (B) AlCl3 (C) BuLi (D) None of these
17. Synthesis of each molecule of glucose in photosynthesis involves: [JEE Main 2013]
(A) 5 molecules of ATP (B) 18 molecules of ATP
(C) 10 molecules of ATP (D) 8 molecules of ATP
18. Which one of the following bases is not present in DNA? [JEE Main 2014]
(A) Cytosine (B) Thymine (C) Quinoline (D) Adenine
19. Which one is classified as a condensation polymer [JEE Main 2014]

(A) Teflon (B) Acrylonitrile (C) Dacron (D) Neoprene
20. Which poloymer is used in the manufacture of paints and lacquers ? [JEE Main 2015]
(A) Bakelite (B) Glyptal (C) Polypropene (D) Poly vinyl chloride
21. Which of the vitamins given below is water soluble? [JEE Main 2015]
(A) Vitamin C (B) Vitamin D (C) Vitamin E (D) Vitamin K
22. Which of the following compounds is not an antacid ? [JEE Main 2015]
(A) Aluminium hydroxide (B) Cimetidine (C) Phenelzine (D) Ranitidine
23. The formation of which of the following poymers involves hydrolysis reaction ? [JEE Main 2017]
(A) Bakelite (B) Nylon 6, 6 (C) Terylene (D) Nylon 6
24. Which of the following compounds will behave as a reducing sugar in an aqueous KOH solution ?
[JEE Main 2017]
HOH2C
O CH 2OCH 3
OH
(A) (B) (C) (D)
OH
OH
25. Glucose on prolonged heating with HI gives [JEE Main 2018]

(A) 6-iodohexanal (B) n-Hexane (C) 1-Hexene (D) Hexanoic acid
26. The predominant form of histamine present in human blood is (pKa, Histidine = 6.0) [JEE Main 2018]
H H
N N
(A) NH 3 (B) NH 2
N N
H
N
(C) NH 3 (D)
N
27. Which of the given statements in incorrect about glycogen ? [JEE Mains 2019]
(A) It is straight chain polymer similar to amylose
(B) Only -linkages are present in the molecule
(C) It is present in animal cells
(D) It is present in some yeast and fungi
28. Which of the following statement is not true about RNA? [JEE Mains 2019]
(A) It controls the synthesis of protein
(B) It has always double stranded -helix structure
(C) It usually does not replicate
(D) It is present in the nucleus of the cell
29. Number of stereo-centres present in linear and cyclic structures of glucose are respectively
[JEE Mains 2019]
(A) 4 and 5 (B) 4 and 4 (C) 5 and 4 (D) 5 and 5
30. Amylopectin is composed of [JEE Mains 2019]

(A)  -D-glucose, C1-C4 and C2-C6 linkages (B) -D-glucose, C1-C4 and C2-C6 linkages
(C)  -D-glucose, C1-C4 and C1-C6 linkages (D) -D-glucose, C1-C4 and C1-C6 linkages
31. The peptide that gives positive ceric ammonium nitrate and carbylamine tests is [JEE Mains 2019]
(A) Lys-Asp (B) Ser-Lys (C) Gln-Asp (D) Asp-Gln
32. Which of the following statement is not true about sucrose ? [JEE Mains 2019]
(A) It is also named as invert sugar
(B) The glycosidic linkage is present between C1 of -glucose and C1 of  -fructose
(C) It is a non-reducing sugar
(D) On hydrolysis, it produces glucose and fructose
33. Fructose and glucose can be distinguished by [JEE Mains 2019]

(A) Fehling’s test (B) Barfoed’s test (C) Benedict’s test (D) Seliwanoff’s test
34. Maltose on treatment with dilute HCl gives [JEE Mains 2019]
(A) D-glucose and D-fructose (B) D-fructose
(C) D-galactose (D) D-glucose
35. Which of the following tests cannot be used for identifying amino acids ? [JEE Mains 2019]
(A) Barfoed test (B) Ninhydrin test (C) Xanthoproteic test (D) Biuret test
36. The increasing order of pKa of the following amino acids in aqueous solution is Gly, Asp, Lys, Arg
(A) Asp < Gly < Arg < Lys (B) Arg < Lys < Gly < Asp [JEE Mains 2019]
(C) Gly < Asp < Arg < Lys (D) Asp < Gly < Lys < Arg
37. Consider the following reactions : [JEE Mains 2020]

x.eq.of
dry HCl
(i) Glucose + ROH   Acetal 
(CH3CO)2 O
 acetyl derivative
Ni/H2 y eq.of
(ii) Glucose   A 
(CH3CO)2 O
z eq.of
(iii) Glucose 
(CH3CO)2 O
'x', 'y' and 'z' in these reactions are respectively :

(A) 5, 6 & 6 (B) 4, 5 & 5 (C) 4, 6 & 5 (D) 5, 4 & 5
38. The correct observation in the following reaction is: [JEE Mains 2020]
(A) Formation of blue colour (B) Formation of violet colour

(C) Formation of red colour (D) Gives no colour
39. The number of groups present in a tripeptide Asp–Glu-Lys is [JEE Mains 2020]
40. What are the functional groups present in the structure of maltose ? [JEE Mains 2020]
(A) Two acetals (B) One acetal and one ketal
(C) One ketal and one hemiketal (D) One acetal and one hemiacetal
41. Which of the following is not an essential amino acid ? [JEE Mains 2020]
(A) Tyrosine (B) Valine (C) Leucine (D) Lysine
42. The number of chiral carbon(s) present in peptide, IIe-Arg-Pro, is ........ . [JEE Mains 2020]
43. The number of chiral carbons present in sucrose is........... [JEE Mains 2020]
44. Which one of the following statement is not true ? [JEE Mains 2020]
(A) Lactose contains -glycosidic linkage between C1 of galactose and C4 of glucose
(B) On acid hydrolysis, lactose gives one molecule of D(+) - glucose and one molecule of D(+)-galactose.
(C) Lactose is a reducing sugar and it gives Fehling's test.
(D) Lactose (C11H22O11) is a disaccharide and it contains 8 hydroxyl groups.
45. Which of the following polymers is not obtained by condensation polymerisation ? [JEE Main 2020]
(A) Nylon 6, 6 (B) Buna – N (C) Bakelite (D) Nylon 6
46. Consider the Assertion and Reason given below : [JEE Main 2020]
Assertion (A) : Ethene polymerized in the presence of Ziegler Natta Catalyst at high temperature and pressure
is used to make buckets and dustbins.
Reason (R) : High density polymers are closely packed and are chemically inert. Choose the correct answer
from the following :
(A) Both (A) and (R) are correct but (R) is not the correct explanation of (A).
(B) Both (A) and (R) are correct and (R) is the correct explanation of (A).
(C) (A) is correct but (R) is wrong.
(D) (A) and (R) both are wrong.
47. The correct match between Item-1 and Item-II is : [JEE Main 2020]
Item-I
(a) Natural rubber (I) 1, 3-butadiene + styrene
(b) Neoprene (II) 1, 3-butadiene + acrylonitrile
(c) Buna-N (III) Chloroprene
(d) Buna-S (IV) Isoprene
(A) (a)-(IV), (b)-(III), (c)-(II), (d)-(I) (B) (a)-(III), (b)-(IV), (c)-(III), (d)-(I)
(C) (a)-(IV), (b)-(III), (c)-(I), (d)-(II) (D) (a)-(III), (b)-(IV), (c)-(I), (d)-(II)
48. In polymer Buna-S ; ‘S’ stands for : [JEE-Mains (24-Feb_Shift -2)2021]

(A) Styrene (B) Sulphur (C) Strength (D) Sulphonation
49. Match List I with List II. [JEE-Mains (24-Feb_Shift -1)2021]

List I List II
(Monomer Unit) (Polymer)
(a) Caprolactum (i) Natural rubber
(b) 2-Chloro-1,3-butadiene (ii) Buna-N
(c) Isoprene (iii) Nylon 6
(d) Acrylonitrile (iv) Neoprene
(A) (a)  (iii), (b)  (iv), (c)  (i), (d)  (ii)
(B) (a)  (i), (b)  (ii), (c)  (iii), (d)  (iv)
(C) (a)  (ii), (b)  (i), (c)  (iv), (d)  (iii)
(D) (a)  (iv), (b)  (iii), (c)  (ii), (d)  (i)
50. Which statement is correct ? [JEE-Mains (25-Feb_Shift -1)2021]
(A) Buna-S is a synthetic and linear thermosetting polymer
(B) Neoprene is addition copolymer used in plastic bucket manufacturing
(C) Synthesis of Buna-S needs nascent oxygen
(D) Buna-N is a natural polymer
51. The structure of Neoprene is : [JEE-Mains (26-Feb_Shift -1)2021]
—CH2 —CH — Cl
n
(A) (B) —CH —C CH — CH2 —
2
CN n
—HN N NHCH 2—
N N —CH2 CH CH — CH2 — CH2 — CH —n

(C) (D)
NH CN
52. Which of the following polymer is used in the manufacture of wood laminates ?
(A) Melamine formaldehyde resin (B)cis-poly isoprene
(C) Phenol and formaldehyde resin (D) Urea formaldehyde resin
53. Which of the following is correct structure of -anomer of maltose : [JEE-Mains (25-Feb_Shift -2)2021]
CH2OH CH 2OH
H O H H O OH
H H
OH H OH H
(A) HO H
O
H OH H OH
CH2OH CH 2OH
H O H H O
OH
H H
H H H H
(B) HO O H
OH OH HO OH
CH2OH CH 2OH
H O H H O
H
H H
H H H H
(C) HO OH
O
HO OH HO OH
CH2OH CH2OH
H O H H O
H
H H
OH H OH H
(D) HO OH
O
H OH H OH
54. Which of the glycosidic linkage galactose and glucose is present in lactose ?
(A) C-1 of glucose and C-6 of galactose [JEE-Mains (25-Feb_Shift -1)2021]
(B) C-1 of galactose and C-4 of glucose
(C) C-1 of glucose and C-4 of galactose
(D) C-1 of galactose and C-6 of glucose
55. Match List-I with List-II. [JEE-Mains (26-Feb_Shift -2)2021]

List-I List-II
(a) Sucrose (i) -D-Galactose and -D-Glucose
(b) Lactose (ii) -D-Glucose and -D-Fructose
(c) Maltose (iii) -D- Glucose and -D-Glucose
(A) (a)-(iii), (b)-(ii), (c)-(i) (B) (a)-(iii), (b)-(i), (c)-(ii)
(C) (a)-(i), (b)-(iii), (c)-(ii) (D) (a)-(ii), (b)-(i), (c)-(iii)
56. Seliwanoff test and Xanthoproteic test are used for the identification of __________ and ___________
respectively [JEE-Mains (26-Feb_Shift -2)2021]
(A) ketoses, proteins (B) proteins, ketoses
(C) aldoses, ketoses (D) ketoses, aldoses
57. Which of the following vitamin is helpful in delaying the blood clotting ? [JEE-Mains (26-Feb_Shift -1)2021]
(A) Vitamin B (B) Vitamin C (C) Vitamin K (D) Vitamin E
58. Deficiency of vitamin K causes: [JEE-Mains (18-March_Shift -1)2021]

(A) Cheilosis (B) Increase in blood clotting time
(C) Increase in fragility of RBC’s (D) Decrease in blood clotting time
59. Which among the following pairs of Vitamins is stored in our body relatively for longer duration?
(A) Ascorbic acid and Vitamin D [JEE-Mains (16-March_Shift -1)2021]
(B) Thiamine and Ascorbic acid
(C) Vitamin A and Vitamin D
(D) Thiamine and Vitamin A
60. The secondary structure of protein is stabilised by: [JEE-Mains (16-March_Shift -2)2021]
(A)van der Waals forces (B) Peptide bond
(C) Hydrogen bonding (D)glycosidic bond
61. Which of the following is correct structure of tyrosine ? [JEE-Mains (17-March_Shift -1)2021]
COOH COOH
H 2N H H 2N H
OH
(A) (B)
OH
COOH COOH
H 2N H H 2N H
OH
(C) (D)
OH
62. Fructose is an example of : [JEE-Mains (17-March_Shift -2)2021]

(A) Heptose (B) Aldohexose (C) Pyranose (D) Ketohexose
63. A non-reducing sugar ”A” hydrolyses to give two reducing mono saccharides. Sugar A is:
(A) Glucose (B) Fructose (C) Sucrose (D) Galactose
64. Orlon fibres are made up of: [JEE-Mains (20-July_Shift -1)2021]

(A) Polyacrylonitrile (B) Cellulose
(C) Polyamide (D) Polyesters
65. Identify the incorrect statement from the following : [JEE-Mains (20-July_Shift -1)2021]
(A) Glycogen is called as animal starch
(B) -Glycosidic linkage makes cellulose polymer
(C) Amylose is a branched chain polymer of glucose
(D) Starch is a polymer of -D glucose
66. The correct structure of Rhumann’s Purple, the compound formed in the reaction of ninhydrin with proteins is
: [JEE-Mains (20-July_Shift -1)2021]
O– O– O O–
(1) N (2) N
O O
O O
–
O O O– O–
+
(3) N=N— N (4) N
O O O O
67. Which one of the following statements is not true about enzymes ? [JEE-Mains (20-July_Shift-2)2021]
(A) Enzymes work as catalysts by lowering the activation energy of a biochemical reation.
(B) The action of enzymes is temperature and pH specific.
(C) Almost all enzymes of proteins.
(D) Enzymes are non–specific for a reaction and substrate.
68. Bakelite is a cross-linked polymer of formaldehyde and : [JEE-Mains (20-July_Shift-2)2021]
(A) Buna-S (B) Dacron (C) Novolac (D) PHBV
69. Match List-I with List-II : [JEE-Mains (22-July_Shift-2)2021]
(a) Chloroprene (i)
Cl
(b) Neoprene (ii)
Cl
(c) Acrylonitrile (iii) n
(d) Isoprene (iv) CH2 = CH – CN

(A) (a)-(ii), (b)-(i), (c)-(iv), (d)-(iii)
(B) (a)-(ii), (b)-(iii), (c)-(iv), (d)-(i)
(C) (a)-(iii), (b)-(iv), (c)-(ii), (d)-(i)
(D)(a)-(iii), (b)-(i), (c)-(iv), (d)-(ii)
70. Thiamine and pyridoxine are also known respectively as :

(A) Vitamin B2 and Vitamin E [JEE-Mains (22-July_Shift-2)2021]
(B) Vitamin B1 and Vitamin B6
(C) Vitamin B6 and Vitamin B2
(D) Vitamin E and Vitamin B2
71. Sodium stearate CH3(CH2)16COO–Na+ is an anionic surfactant which forms micelles in oil.
Choose the correct statement for it from the following: [JEE-Mains (25-July_Shift -1)2021]
(A) It forms spherical micelles with CH3(CH2)16– group pointing towards the center of sphere.
(B) It forms non–spherical micelles with CH3(CH2)16– group pointing towards the center.
(C) It forms spherical micelles with CH3(CH2)16– group pointing towards the surface of sphere.
(D) It forms non–spherical micelles with —COO group pointing outwards on the surface.
72. is a repeating unit for:–

(A)Novolac (B)Acrilan
(C) Buna–N (D) Neoprene
73. The water soluble protein is : [JEE-Mains (25-July_Shift -1)2021]

(A)Fibrin (B)Albumin (C)Collagen (D)Myosin
74. What is the major product “P” of the following reaction ? [JEE-Mains (25-July_Shift-2)2021]
CH3
(i)NaNO , HCl,278K

2
 P
NH2 (ii) H2O
(major product)
CH3 OH
(A) Cl (B) 
N2 Cl
CH3 CH3
(C) OH (D) CH3
75. A biodegradable polyamide can be made from: [JEE-Mains (25-July_Shift-2)2021]

(A)Hexamethylene diamine and adipic acid
(B)Styrene and caproic acid
(C)Glycine and aminocaproic acid
(D)Glycine and isoprene
O
H
H3C
N
76. H N O [JEE-Mains (27-July_Shift-1)2021]

(A)
The compound ‘A’ is a complementary base of ______ in DNA stands.

(A) Cytosine (B) Adenine (C) Guanine (D) Uracil
77. Which one among the following chemical tests is used to distinguish monosaccharide from disaccharide?
(A) Barfoed test (B) Seliwanoff’s test
(C) Tollen’s test (D) Iodine test
78. Match List-I with List-II : [JEE-Mains (27-July_Shift-1)2021]

(Drug) (Class of Drug)
(a)Furacin (i) Antibiotic
(b)Arsphenamine (ii) Tranquilizers
(c)Dimetone (iii) Antiseptic
(d)Valium (iv) Synthetic antihistamines
Choose the most appropriate match :
(A) (a)-(iii), (b)-(iv), (c)-(ii),(d)-(i) (B) (a)-(i), (b)-(iii), (c)-(iv),(d)-(ii)
(C) (a)-(ii), (b)-(i), (c)-(iii), (d)-(iv) (D) (a)-(iii), (b)-(i), (c)-(iv),(d)-(ii)
79. Compound A gives D-Galactose and D-Glucose on hydrolysis. The compound A is:
(A) Lactose (B) Amylose (C) Sucrose (D) Maltose
Statement I: Penicillin is bacteriostatic type antibiotic.
Statement II: The general structure of Penicillin is:
Choose the correct option:

(A) Statement I is correct but statement II is false
(B)Statement I is incorrect but statement II is true
(C)Both statement I and statement II are false
(D)Both statement I and statement II are true
81. The polymer formed on heating Novolac with formaldehyde is : [JEE-Mains (26-August_Shift-1)2021]
(A) Polyester (B) Melamine
(C) Nylon 6, 6 (D) Bakelite
82. The total number of negative charge in the tetrapeptide, Gly-Glu-Asp-Tyr at pH 12.5 will be _______ . (Integer
answers) [JEE-Mains (26-August_Shift-1)2021]
83. Given below are two statements : one is labelled as Assertion (A) and the other is labelled as
Reason (R) [JEE-Mains (26-August_Shift-2)2021]
Assertion (A) : Sucrose is a disaccharide and non-reducing sugar.
Reason (R) : Sucrose involves glycosidic linkage between C1 of -glucose
Choose the most appropriate answer from the option given below :
(A) Both (A) and (R) are true and (R) is the true explanation of (A).
(B) Both (A) and (R) are true but (R) is not the true explanation of (A).
(C) (A) is false but (R) is true.
(D) (A) is true but (R) is false.
CH3
N CH3
N O
84. (A) (B) N
Cl
HO O OH
CH3
N
CH 2CH2 NH 2
HO
(C) (D)
N
H
O OH
H3CO
The correct statement about (A), (B), (C) and (d) is : [JEE-Mains (27-August_Shift-1)2021]
(A) (A) and (D) are tranquillizers
(B) (B), (C) and (D) are tranquillizers
(C) (B) and (C) are tranquillizers
(D) (A), (B) and (C) are narcotic analgesics
85. Out of following isomeric forms of uracil, which one is present in RNA ?
O
O
HN
HN
(A) (B)
O
N HO N
H
OH
OH
N
N
(C) (D)
O N
HO N
H
86. Which one of the following tests used for the identification of functional groups in organic compounds
does not use copper reagent? [JEE-Mains (27-August_Shift-2)2021]
(A) Seliwanoff’s test (B) Barfoed’s test
(C) Biuret test for peptide bond (D) Benedict test
87. Which one of the following chemicals is responsible for the production of HCl in the stomach leading to irritation
and pain? [JEE-Mains (27-August_Shift-2)2021]
H CO
NNH 2 NH
(A) (B)
SO2
NH2
HO HN
(C) (D) NH2
N N
H
88. Hydrolysis of sucrose gives : [JEE-Mains (27-August_Shift-2)2021]

(A) -D-(+)-Glucose and -D-(-)-Fructose
(B) D-(-)-Glucose and -D-(+)-Fructose
(C) -D-(+)-Glucose and -D-(-)-Fructose
(D) -D-(-)-Glucose and -D-(-)-Fructose
89. Which one of the following compounds contains -C1-C4 glycosidic linkage ?
(A) Lactose (B) Sucrose
(C) Maltose (D) Amylose
90. Monomer of Novolac is : [JEE-Mains (31-August_Shift-1)2021]
(A) 1,3-Butadiene and styrene. (B) Phenol and melamine.
(C) o-Hydroxymethylphenol. (D) 3-Hydroxybutanoic acid.
91. Which among the following is not a polyester? [JEE-Mains (31-August_Shift-2)2021]

(A)Glyptal (B) PHBV (C) Dacron (D)Novolac
92. Which of the following is NOT an example of fibrous protein? [JEE-Mains (31-August_Shift-2)2021]
(A) Myosin (B) Collagen (C) Keratin (D) Albumin
93. In the following sequence of reactions,

+
H /H 2O KOI
C3 H 6 A B+C
dil KOH
The compounds B and C respectively are : [JEE-Mains (1-September_Shift-2)2021]

(A) CI3COOK, HCOOH (B) CI3COOK, CH3I
(C) CHI3, CH3 COOK (D) CH3I, HCOOK
94. Monomer units of Dacron polymer are : [JEE-Mains (1-September_Shift-2)2021]

(A) ethylene glycol and phthalic acid (B) ethylene glycol and terephthalic acid
(C) glycerol and phthalic acid (D) glycerol and terephtalic acid
95. A peptide synthesized by the reactions of one molecule each of Glycine, Leucine, Aspartic acid and Histidine will
have _____ peptide linkages. [JEE-Mains (1-September_Shift-2)2021]
96. A polysaccharide ‘ X’ on boiling with dil H2SO4 at 393 K under 2-3 atm pressure yields ‘ Y’. ‘ Y ‘ on
treatment with bromine water gives gluconic acid. ‘ X’ contains -glycosidic linkages only. Compound
‘ X’ is : [JEE-Mains (24-Jun-Shift-1)2022]
(A) starch (B) cellulose (C) amylose (D)amylopectin
97. When sugar ‘X‘ is boiled with dilute H2SO4 in alcoholic solution, two isomers ‘ A and ‘ B are formed. ‘
A oxidation with HNO3 yields saccharic acid where as ‘ B is laevorotatory. The compound ‘ X ‘ is:
(A) Maltose (B) Sucrose (C)Lactose (D) Strach
Zymase NaOI
98. C6H12O6   A 
B  CHI3
 [JEE-Mains (29-Jun-Shift-1)2022]
The number of carbon atoms present in the product B is_______.
99. Glycosidic linkage between C1 of -glucose and C2 of -fructose is found in

(A) Maltose (B) sucrose (C) lactose (D) amylose
100. Which one of the following is a reducing sugar ? [JEE-Mains (26-July_Shift-1)2022]

OH
H C
H C OH HOCH2 O H
HO C H O H H
(A) H C OH (B) H OCH3
H C OH OH
H
OCH3
HOH2C O H H O CH2OH
H OCH3
H H H H H OH
(C) H O H (D) HO H
OH OH OH OH H OH
H OH
CH2OH
101. Animal starch is the other name of [JEE-Mains (26-July_Shift-2)2022]

(A) amylose (B) maltose (C) glycogen (D) amylopectin
102. A sugar ‘X’ dehydrates very slowly under acidic condition to give furfural which on further reaction
with resorcinol gives the coloured product after sometimes. [JEE-Mains (27-July_Shift-1)2022]
(A) Aldopentose (B) Aldotetrose (C) Oxalic acid(D) Ketotetrose
103. Match List - I with List - II. [JEE-Mains (27-July_Shift-2)2022]

List - I List - II
(A) Glucose + HI (I) Gluconic acid
(B) Glucose +Br2 water (II) Glucose pentacetate
(C) Glucose + acetic anhydride (III) Saccharic acid
(D) Glucose +HNO3 (IV) Hexane
(A) A-IV, B-I,C-II,D-III (B) A-IV, B-III, C-II,D-I
(C) A-III, B-I, C-IV, D-II (D) A-I, B-III, C-IV, D-II
104. For the below given cyclic hemiacetal (X), the correct pyranose structure is :
HO C H
HO C H O
H C OH
HO C H
H C
CH2OH
(X)
HO HO HO HO
O OH O OH O OH O
OH
OH OH OH OH
(A) (B) (C) (D)
OH OH OH OH
OH OH OH OH
105. The formulas of A and B for the following reaction sequence
HCN
+ A
H3 O
Fructose
(i) NaBH 4
B
(ii) HI/P
(A) A = C7H14O8, B=C6H14 (B) A=C7H13O7, B=C7H14O

(C) A=C7H12O8, B=C6H14 (D) A=C7H14O8, B=C6H14O6
106. Given below are two statements. One is labelled as Assertion A and the other is labelled as Reason R.
Assertion A: Amylose is insoluble in water. [JEE-Mains (29-July_Shift-2)2022]
Reason R: Amylose is a long linear molecule with more than 200 glucose units. In the light of the above
statements, choose the correct answer from the options : given below.
(C) A is correct but R is not correct
(D) A is not correct but R is correct
107. During the denaturation of proteins, which of these structures will remain intact ?
(A) Primary (B) Secondary (C) Tertiary (D) Quaternary
108. Which of the following compounds is an example of hypnotic drug? [JEE-Mains (29-July_Shift-1)2022]
(A) Seldane (B) Amytal (C) Aspartame (D) Prontosil
109. In a linear tetrapeptide (Constituted with different amino acids), (number of amino acids) - (number of peptide
bonds) is [JEE-Mains (29-July_Shift-1)2022]
110. Melamine polymer is formed by the condensation of : [JEE-Mains (25-July_Shift-1)2022]
H2N N NH2 H2N NH2
+ HCHO + HCHO
N N N N
(A) (B)
NH2 NH2
H2N NH2 NH2
+ HCHO + HCHO
N
(C) (D)
NH2 NH2
111. Match List I with List II : [JEE-Mains (25-July_Shift-2)2022]
List I List II
Polymer used for items
A. Nylon 6,6 I. Buckets
B. Low density polythene II. Non-stick utensils
C. High density polythene III. Bristles of brushes
D. Teflon IV. Toys
(A) A-III, B-I, C-IV, D-II (B) A-III, B-IV, C-I, D-II
(C) A-II, B-I, C-IV, D-III (D) A-II, B-IV, C-I, D-III
112. Vulcanization or rubber is carried out by heating a mixture of [JEE-Mains (26-July_Shift-2)2022]

(A) Isoprene and styrene (B) neoprene and sulphur
(C) isoprene and sulphur (D) Neoprene and styrene
113. Match List I with List II [JEE-Mains (27-July_Shift-1)2022]

List I (Polymers) List II (Commercial names)
(A) Phenol-formaldehyde resin (I) Glyptal
(B) Copolymre of 1, 3-butadiene and styrene (II) Novolac
(C) Polyester of glycol and phthalic acid (III) Buna-S
(D) Polyester of glycol and terephthalic acid (IV) Dacron
(A) A-II, B-III, C-IV, D-I (B) A-II, B-III, C-I, D-IV
(C) A-II, B-I, C-III, D-IV (D) A-III, B-II, C-IV, D-I

List - I
(Polymer) (Monomer)
(A) Neoprene (I) Acrylonitrile
(B) Teflon (II) Chloroprene
(C) Acrilan (III) Tetrafluoroethene
(D) Natural rubber (IV) Isoprene
(A) A-II,B-III,C-I, D-IV (B) A-II, B-I, C-III, D-IV
(C) A-II, B-I, C-IV, D-III (D) A-I, B-II, C-III, D-IV
115. Terylene polymer is obtained by condensation of : [JEE-Mains (28-July_Shift-)2022]

(A) Ethane-1,2-diol and Benzene-1, 3 dicarboxylic acid
(B) Propane-1, 2-diol and Benzene-1, 4 dicarboxylic acid
(C) Ethane-1, 2-diol and Benzene-1, 4 dicarboxylic acid
(D) Ethane-1, 2-diol and Benzene-1, 2 dicarboxylic acid
116. Which of the following is NOT a natural polymer? [JEE-Mains (29-July_Shift-2)2022]

(A) Protein (B) Starch (C) Rubber (D) Rayon
117. Drugs used to bind to receptors, inhibiting its natural function and blocking a message are called :
(A) Agonists (B) Antagonists (C) Allosterists (D) Anti histaminists
118. Some drugs bind to a site other than the active site of an enzyme. This site is
(A) Non-acitve site (B) allosteric site
(C) Competitive site (D) Therapeutic site
119. Stearic acid and polyethylene glycol react to form which one of the following soap/s detergents ?
(A) Cationic detergent (B) Soap
(C) Anionic detergent (D) Non-ionic detergent
120. How many of the following drugs is/are examples of broad spectrum antibiotics ?
Ofloxacin, Penicillin G, Terpineol, Salvasan. [JEE-Mains (26-July_Shift-2)2022]
121. Match List I with List II. [JEE-Mains (27-July_Shift-1)2022]

List I List II
NCH3
(A) (I) Anti-depressant
HO O OH
OH
(B) (II) 550 times sweeter than cane sugar

H3C CH3
Cl
NHNH2
(C) (III) Narcotic analgesic
C
NH
(D) (IV) Antiseptic
S
O O

(A) A-IV, B-III, C-II, D-I (B) A-III, B-I, C-II, D-IV
(C) A-III, B-IV, C-I, D-II (D) A-III, B-I, C-IV, D-II
122. Which of the following enhances the lathering property of soap? [JEE-Mains (27-July_Shift-2)2022]
(A) Sodium stearate (B) Sodium carbonate
(C) Sodium rosinate (D) Trisodium phosfhate
123. Statements about Enzyme Inhibitor Drugs are given below:
(A) There are Competitive and Non-competitive inhibitor drugs. [JEE-Mains (28-July_Shift-1)2022]
(B) These can bind at the active sites and allosteric sites.
(C) Competitive Drugs are allosteric site blocking drugs.
(D) Non-competitive Drugs are active site blocking drugs.
(A) (A), (D) only (B) (A), (C) only (C) (A), (B) only (D) (A), (B),(C) only
124. Two statements in respect of drug-enzyme interaction are given below

Statement I : Action of an enzyme can be blocked only when an inhibitor blocks the active site of the
enzyme. [JEE-Mains (28-July_Shift-2)2022]
Statement II : An inhibitor can form a strong covalent bond with the enzyme. In the light of the above
statements, choose the correct answer from the options given below
(A) Both Statement I and Statement II are true
(B) Both Statement I and Statement II are false
(C) Statement I is true but Statement II is false
(D) Statement I is false but Statement II is true
125. Which among the following pairs has only herbicides?

(A) Aldrin and Dieldrin [JEE-Mains (29-July_Shift-1)2022]
(B) Sodium chlorate and Aldrin
(C) Sodium arsinate and Dieldrin
(D) Sodium chlorate and sodium arsinite.
126. The number of chlorine atoms in bithionol is _____ [JEE-Mains (29-July_Shift-2)2022]
127. Which of the following is an example of polyester ? [JEE-Mains (24-Jun-Shift-1)2022]

(A) Butadiene-styrene copolymer
(B) Melamine polymer
(C) Neoprene
(D) Poly- -hydroxybutyrate-co- -hydroxyvalerate
128. Which of the following is not an example of a condensation polymer?

(A) Nylon 6.6 (B) Decron (C) Buna-N (D) Silicone
129. Which of the following sets are correct regarding polymer? [JEE-Mains (26-Jun-Shift-1)2022]
(A) Copolymer : Buna-S (B) Condensation polymer : Nylon-6,6
(C) Fibres : Nylon-6,6 (D) Thermosetting polymer : Terylene
(E) Homopolymer : Buna-N
Choose the correct answer from given options below :
(A) A,B and C are correct (B) B,C and D are correct
(C) A,C and E are correct (D) A,B and D are correct
130. Match List - I with List - II. [JEE-Mains (27-Jun-Shift-1)2022]

List – I List - II
(Polymer) (Used in)
(A) Bakelite (I) Radio and television cabinets
(B) Glyptal (II) Electrical switches
(C) PVC (III) Paints and Lacquers
(D) Polystyrene (IV) Water pipes
(A) (A) – (II), (B) – (III), (C) – (IV), (D)- (I)
(B) (A) – (I), (B) – (II), (C) – (III), (D)- (IV)
(C) (A) – (IV),(B) – (III), (C) – (II), (D)- (I)
(D) (A) – (II), (B) – (III), (C) – (I), (D)- (IV)
131. Which is true about Buna-N? [JEE-Mains (27-Jun-Shift-2)2022]

(A) It is a linear polymer of 1,3 -butadiene.
(B) It is obtained by copolymerization of 1,3 -butadiene and styrene.
(C) It is obtained by copolymerization of 1,3 -butadiene and acrylonitrile.
(D) The suffix N in Buna- N stands for its natural occurrence.
132. Which one of the following is NOT a copolymer ? [JEE-Mains (28-Jun-Shift-1)2022]

(A) Buna-S (B) Neoprene (C) PHBV (D) Butadiene-styrene
133. Given below are two statements, one is Assertion (A) and other is Reason (R).
Assertion (A) : Natural rubber is a linear polymer of isoprene called cis-polyisoprene with elastic
properties.
Reason (R) : The cis-polyisoprene molecules consist of various chains held together by strong polar
interactions with coiled structure.
Question: In the light of the above statements, choose the correct one from the options given below:
(A) Both (A) and (R) are true and (R) is the correct explanation of (A).
(B) Both (A) and (R) are true but (R) is not the correct explanation of (A).
(C) (A) is true but (R) is false.
(D) (A) is false but (R) is true.
134. The polymer, which can be stretched and retains its original status on releasing the force is
(A) Bakelite. (B) Nylon 6,6. (C) Buna-N. (D) Terylene.
135. Given below are two statements: one is labelled as Assertion A and the other is labelled as Reason R.
Assertion A: Dacron is an example of polyester polymer. [JEE-Mains (29-Jun-Shift-2)2022]
Reason R: Dacron is made up of ethylene glycol and terephthalic acid monomers. In the light of the
above statements, choose the most appropriate answer from the Question: options given below.
(C) A is correct but R is not correct.
(D) A is not correct but R is correct.
Protion and DNA RNA

136. Inalanylglycylleucylalanylvaline. the number of peptide linkages is [JEE-Mains (24-Jun-Shift-2)2022]
137. How many of the given compounds will give a positive Biuret test ?
Glycine, Glycylalanine, Tripeptide, Biuret [JEE-Mains (25-Jun-Shift-2)2022]
138. The number of oxygens present in a nucleotide formed from a base, that is present only in RNA is
139. Which one of the following is a water soluble vitamin, that is not excreted easily?
(A) Vitamin B2 (B) Vitamin B1 (C) Vitamin B6 (D) Vitamin B12
140. Question: Stability of - Helix structure of proteins depends upon [JEE-Mains (28-Jun-Shift-1)2022]
(A) dipolar interaction (B) H-bonding interaction
(C) van der Waals forces (D) -stacking interaction
141. Sugar moiety in DNA and RNA molecules respectively are [JEE-Mains (29-Jun-Shift-1)2022]
(A) -D-2-deoxyribose, -D-deoxyribose. (B) -D-2-deoxyribose, -D-ribose
(C) -D-ribose,-D-2-deoxyribose. (D) -D-deoxyribose, -D-2-deoxyribose.
142. The structure of protein that is unaffected by heating is [JEE-Mains (29-Jun-Shift-2)2022]

(A) secondary structure (B) tertiary structure
(C) primary structure (D)quaternary structure
Chemistry in everyday life

143. Which of the following is not a broad spectrum antibiotic ? [JEE-Mains (24-Jun-Shift-1)2022]
(A) Vancomycin (B) Ampicillin (C) Ofloxacin (D) Penicillin G
144 The structure shown below is of which well-known drug molecule? [JEE-Mains (24-Jun-Shift-2)2022]
H
CH3 CN
N
N
S
N NHCH3
H
(A) Ranitidine (B) Seldane (C) Cimetidine (D) Codeine
145. Using very little soap while washing clothes, does not serve the purpose of cleaning of clothes, because :
(A)soap particles remain floating in water as ions. [JEE-Mains (25-Jun-Shift-1)2022]
(B) the hydrophobic part of soap is not able to take away grease.
(C) the micelles are not formed due to concentration of soap, below its CMC value.
(D) colloidal structure of soap in water is completely disturbed.
146. Which one of the following is an example of artificial sweetner ? [JEE-Mains (25-Jun-Shift-1)2022]
(A) Bithional (B) Alitame (C) Salvarsan (D) Lactose
147. An antiseptic dettol is a mixture of two compounds ‘ A ‘ and ‘ B ‘ where A has 6 \ Question: electrons
and B has 2  electrons. What is ‘ B ‘? [JEE-Mains (25-Jun-Shift-2)2022]
(A)Bithionol (B)Terpineol (C)Chloroxylenol (D) Chloramphenicol
148. A chemical which stimulates the secretion of pepsin is: [JEE-Mains (26-Jun-Shift-1)2022]
(A) Anti histamine (B) Cimetidine (C) Histamine (D) Zantac
149. Which of the following is NOT an example of synthetic detergent [JEE-Mains (26-Jun-Shift-2)2022]
- +
(A)CH3 (CH2) 11 SO3 Na (B) CH3 (CH2)16 -
COO Na
+
CH3
(C) CH3 (CH2) 15 N CH3 Br
- (D) CH3(CH2)16COO(CH2CH2O)n CH2CH2OH
CH3
150. Match List - I with List - II. [JEE-Mains (27-Jun-Shift-1)2022]
List - I List - II
+
CH3
-
CH3(CH2)15 N CH3 Br
(A) (I) Dishwashing powder
CH3
SO3- Na
+
(B) CH3 (CH2)11 (II) Toothpaste
(C) C17H35COO–Na++Na2CO3+ Rosinate (III) Laundry soap

(D) CH3(CH2)16COO(CH2CH2O)n CH2CH2OH (IV) Hair conditioner
(A) (A)– (III), (B)– (II), (C) – (IV), (D)– (I)
(B) (A) – (IV), (B) – (II), (C) –(III), (D) – (I)
(C) (A) – (IV), (B) – (III), (C) –(II), (D) – (I)
(D) (A) – (III), (B) – (IV), (C) –(I), (D) – (II)
151. Match List I with List II. [JEE-Mains (27-Jun-Shift-2)2022]
List I List II
(A) Antipyretic I. Reduces pain
(B) Analgesic II. Reduces stress

(C) Tranquilzer III. Reduces fever
(C) Antacid IV. Reduces acidity (stomach)
Question: Choose the correct answer from the options given below:
(A) A-III, B-I, C-II, D-IV (B) A-III, B-I, C-IV, D-II
(C) A-I, B-IV, C-II, D-III (D) A-I, B-III, C-II, D-IV
152. The drug tegametis : [JEE-Mains (28-Jun-Shift-2)2022]

H
N CH(NO 2)
NMe 2
(A) (B) S
N O N NHMe
NH2 H
CH3
N CN
N
N
(C) N S (D)
N NHCH3 Ph HO
H
HO
Ph
153. Which of the following compound does not contain sulfur atom? [JEE-Mains (29-Jun-Shift-1)2022]
(A)Cimetidine (B) Ranitidine (C) Histamine (D) Saccharin
154. Amongst baking soda, caustic soda and washing soda carbonate anion is present in :
(A) washing soda only. (B) washing soda and caustic soda only.
(C) washing soda and baking soda only. (D) baking soda, caustic soda and washing soda.
POC
155. The formula of the purple colour formed in Laissaigne’s test for sulphur using sodium nitroprusside is
(A) NaFe[Fe(CN)6] (B) Na[Cr(NH3)2(NCS)4]
(C) Na2[Fe(CN)5(NO)] (D) Na[Fe(CN)5(NOS)]
156. Given below are two statements : one is labelled as Assertion A and the other is labelled as Reason
R. [JEE-Mains (26-July_Shift-2)2022]
Assertion A : Phenolphthalein is a pH dependent indicator, remains colourless in acidic solution and
gives pink colour in basic medium.
Reason R : Phenolphthalein is a weak acid. It doesn’t dissociate in basic medium. choose the most
appropriate answer from the options given below
(C) A is true but R is false.
(D) A is false but R is true.
157. Match List I with List II. [JEE-Mains (27-July_Shift-1)2022] List

I List II
(A) Benzenesulphonyl chloride (I) Test for primary amines
(B) Hoffmann bromamide reaction (II) Anti Saytzeff
(C) Carbylamine reaction (III) Hinsberg reagent
(D) Hoffmann orientation (IV) Known reaction of Isocyanates
Choose the correct answer from the options given below
(A) A-IV, B-III, C-II, D-I (B) A-IV, B-II, C-I, D-III
(C) A-III, B-IV, C-I, D-II (D) A-IV, B-III,C-I, D-II
158. A compound ‘X’ is acidic and it is soluble in NaOH solution, but insoluble in NaHCO3 solution. Compound
‘X‘ also gives violet colour with neutral FeCl3 solution. The compound ‘ X ‘ is :
OH OH CH2OH CH 2OH
(A) (B) (C) (D)
159. A compound ‘X‘ is a weak acid and it exhibits colour change at pH close to the equivalence point during
neutralization of NaOH with CH3COOH. Compound ‘X‘ Question: exists in ionized form in basic medium.
The compound ‘ X‘ is [JEE-Mains (29-July_Shift-2)2022]
(A) methyl orange (B) methyl red (C) phenolphthalein (D) erichrome Black T
1. Which of the following pairs given positive Tollen’s test ? [IIT 2005]
(A) Glucose, sucrose (B) Glucose, fructose
(C) Hexanal, acetophenone (D) Fructose, sucrose
2. The two forms of D-glucopyranose obtained from the solution of D-glucose are called : [IIT 2005]
(A) isomer (B) anomer (C) epimer (D) enantiomer
3. Match the column [IIT 2006]

Column-I Column-II
(A) Cellulose (P) natural polymer
(B) nylon-6, 6 (Q) synthetic polymer
(C) protein (R) amide linkage
(D) sucrose (S) glycoside linkage
4. Cellulose upon acetylation with excess acetic anhydride/H2SO4 (catalytic) gives cellulose triacetate whose structure
is [IIT 2007]
AcO
AcO
H OO
H OO H
H AcO
AcO OH H
OAcH O O H
O O H H
H AcO H H OH
AcO H H OAc OH H
OAcH O O H
(A) O O H (B) H
H H H OH
H H OAc OH H
O AcH O H
O H
H OH
H OAc
AcO AcO AcO AcO AcO AcO

H H O H H O
HH O HH O HH O HH O HH O HH O
(C) OAcH OAcH OAcH (D) H H H H H H
O O O H O O O H
H OAc H OAc H OAc OAcOAc OAcOAc OAc OAc
5. Among cellulose, poly (vinyl chloride), nylon and natural rubber, the polymer in which the intermolecular force of
attraction is weakest is : [IIT 2008]
(A) nylon (B) Poly (vinyl chloride)
(C) cellulose (D) natural rubber
6. The correct statement(s) about the following sugars X and Y is (are) [IIT 2009]
CH 2OH
CH2-OH O O
H H
O CH2OH H
H H HOH 2C H H HO OH
H H O
O
OH H OH OH CH 2OH H
HO O
HO OH H H OH H
H OH OH H
(X) H OH
(Y)
(A) X is a reducing sugar and Y is a non-reducing sugar
(B) X is a non-reducing sugar and Y is a reducing sugar
(C) The glucosidic linkages in X and Y are and , respectively
(D) The glucosidic linkages in X and Y are and , respectively
7. The correct statement about the following disaccharide is [IIT 2010]
OH
H O CH2OH O
H (a) H H
(b)
OH H H HO
OH OCH2CH2O CH2OH
H OH OH H
(A) Ring (a) is pyranose with -glycosidic link

(B) Ring (a) is furanose with -glycosidic link
(C) Ring (b) is furanose with -glycosidic link
(D) Ring (b) is pyranose with -glycosidic link
8. What is the total number of basic grops in the following form of lysine ? [IIT 2010]
+
H3N —CH2.CH2.CH2.CH2 O
CH—C
H 2N O–
9. The following carbohydrate is [IIT 2011]
H
OH
H O
HO
HO OH
H
OH
H H
(A) a ketohexose (B) an aldohexose (C) an -furanose (D) an -pyranose
10. When the following aldohexose exists in its\D-configuration, the total number stereoisomers in its pyranose form
is [JEE Adv. 2012]
CHO
CH2
CHOH
CHOH
CHOH
CH2OH
11. The substituents R1 and R2 for nine peptides are listed in the table given blow. How many of these peptides are
positively charged at pH = 7.0? [JEE Adv. 2012]
H3N–CH–CO–NH–CH–CO–NH–CH–CO–NH–CH–COO
H R1 R2 H
Peptide R1 R2
I H H
II H CH3
III CH2COOH H
IV CH2CONH2 (CH 2)4NH2
V CH2CONH2 CH2 CONH2
VI (CH2 )4 NH2 (CH 2)4NH2
VII CH2COOH CH2 CONH2
VIII CH2 OH (CH 2)4NH2
IX (CH2 )4 NH2 CH3
12. The total number of distinct naturally occurring amino acids obtained by complete acidic hydrolysis fo the peptide
shown below is : [JEE Adv. 2012]
O
H
H H N
O O O O
N N N
N N N
N CH2 O O CH2 O
H H
H
O
13. The total number of lone-pairs of electrons in melamine is [JEE Adv. 2013]
14. A tetrapeptide has –COOH group on alanine. This produces glycine (Gly), valine (Val), phenyl alanine (Phe) and
alanine (Ala), on complete hydrolysis. For this tetrapeptite, the number of possible sequencess (primary structures)
with –NH2 group attached to a chiral center is [JEE Adv. 2013]
15. The structure of D-(+)- glucose is [JEE Adv. 2015]
CHO
H OH
HO H
H OH
H OH
CH2OH
The structure of L-(–)glucose is
CHO CHO CHO CHO

HO H H OH HO H HO H
H OH HO H HO H HO H
HO H H OH H OH HO H
(A) (B) (c) (D)
HO H HO H HO H H OH
CH2OH CH2OH CH2OH CH2OH
16. For 'invert sugar' the correct statement(s) is(are) [JEE Adv. 2015]
(Given: specific rotations of (+)-sucrose, (+)-maltose, L-(–)-glucose and L-(+)-fructose in aqueous solution are
+66°, +140°, –52° and +92°, respectively)
(A) 'invert sugar' is prepared by acid catalyzed hydrolysis of maltose
(B) 'invert sugar' is an equimolar mixture of D-(+)-glucose and D-(–)-fructose
(C) specific rotation of 'invert sugar' is –20°
(D) on reaction with Br2 water, 'invert sugar' forms saccharic acid as one of the products
17. On complete hydrogenation, natural rubber produces [JEE Adv. 2016]
(A) ethylene-propylene copolymer (B) vulcanised rubber
(C) polypropylene (D) polybutylene
18. The Fischer presentation of D-glucose is given below. [JEE Adv. 2018]
CHO
H OH
HO H
H OH
H OH
CH3OH
D-glucose
The correct structure(s) of 3-g1ucopyranose is (are) :-
H H CH2OH H
O O O O
CH2OH CH2OH H CH2OH
HO OH HO OH H OH HO H
(A) H H (B) H H (C) HO H (D) H OH

H HO H H OH HO H HO
OH H OH OH H H OH H
19. Which of the following statement(s) is (are) true ? [JEE Adv. 2019]
(A) Oxidation of glucose with bromine water gives glutamic acid
(B) The two six-membered cyclic hemiacetal forms of D-(+)-glucose are called anomers
(C) Monosaccharides cannot be hydrolysed to give polyhydroxy aldehydes and ketones
(D) Hydrolysis of sucrose gives dextrorotatory glucose and laevorotatory fructose
20. Choose the correct option(s) from the following [JEE Adv. 2019]
(A) Teflon is prepared by heating tetrafluoroethene in presence of a persulphate catalyst at high pressure
(B) Natural rubber is polyisoprene containing trans alkene units
(C) Nylon-6 has amide linkages
(D) Cellulose has only -D-glucose units that are joined by glycosidic linkages
21. The structure of a peptide is given below : [JEE Advanced 2020]
If the absolute values of the net charge of the peptide at pH = 2, pH = 6, and pH = 11 are |z1|, |z2|, and |z3|,
respectively, then what is |z1| + |z2| + |z3|?
22. Consider the following reaction [JEE Advance 2022]
OH
red phosphours
R (major product)
Br 2
Br
On estimation of bromine in 1.00 g of R using Carius method, the amount of AgBr formed (in g) is
________.
[Given: Atomic mass of H = 1, C = 12, O = 16, P = 31, Br = 80, Ag = 108]
23. Match the compounds in LIST-I with the observations in LIST-II, and choose the correct option.
LIST-I LIST-II
(I) Aniline (P) Sodium fusion extract of the compound on boiling with
FeSO4, followed by acidification with conc. H2SO4, gives
Prussian blue color.
(II) o-Cresol (Q) Sodium fusion extract of the compound on treatment
with sodium nitroprusside gives blood red color.
(III) Cysteine (R) Addition of the compound to a saturated solution of
NaHCO3 results in effervescence.
(IV) Caprolactam (S) The compound reacts with bromine water to give a
white precipitate.
(T) Treating the compound with neutral FeCl3 solution
produces violet color.
(A) IP,Q ; IIS ; IIIQ,R ; IVP [JEE Advance 2022]
(B) IP ; IIR,S ; IIIR ; IVQ,S

(C) IQ,S ; IIP,T ; IIIP ; IVS
(D) IP,S ; II T ; IIIQ,R ; IVP
24. Among the following, the correct statement(s) about polymers is(are) [JEE Advance 2022]
(A) The polymerization of chloroprene gives natural rubber.
(B) Teflon is prepared from tetrafluoroethene by heating it with persulphate catalyst at high pressures.
(C) PVC are thermoplastic polymers.
(D) Ethene at 350-570 K temperature and 1000-2000 atm pressure in the presence of a peroxide
initiator yields high density polythene.
25. Treatment of D-glucose with aqueous NaOH results in a mixture of monosaccharides, which are
CHO CHO CHO
HO H H OH HO H
HO H HO H HO H
H OH , HO H and HO H
(A) [JEE Advance 2022]
H OH H OH H OH
CH2OH CH2OH CH2 OH
CH2OH CHO CHO
O HO H HO H
HO H H OH HO H
, and
H OH H OH HO H
(B)
H OH H OH H OH
CH2OH CH2OH CH2 OH
CHO CH2OH CHO
H OH O HO H
HO H HO H HO H
, and
H OH H OH H OH
(C)
H OH H OH H OH
CH2OH CH2OH CH2OH
CHO CHO CHO
H OH H OH HO H
HO H HO H HO H
, and
HO H H OH H OH
(D)
H OH H OH H OH
CH2OH CH2OH CH2OH

1. D 2. A 3. A 4. B 5. C 6. A 7. B
8. C 9. C 10. C 11. ABCD 12. B 13. B 14. B
15. A 16. B 17. B 18. C 19. C 20. B 21. A
22. C 23. D 24. D 25. B 26. A 27. A 28. B

29. A 30. D 31. B 32. B 33. D 34. D 35. A
36. D 37. C 38. C 39. 5 40. 4 41. A 42. 4
43. 9 44. A 45. B 46. B 47. A 48. A 49. A
50. C 51. B 52. A 53. D 54. B 55. D 56. A
57. C 58. B 59. C 60. C 61. C 62. D 63. C
64. A 65. C 66. B 67. D 68. C 69. B 70. B
71. A 72. A 73. B 74. C 75. C 76. B 77. A
78. D 79. A 80. B 81. D 82. 4 83. D 84. C
85. A 86. A 87. D 88. A 89. A 90. C 91. D
92. D 93. C 94. B 95. 3 96. B 97. B 98. 1
99. B 100. A 101. C 102. A 103. A 104. D 105. A
106. D 107. A 108. B 109. 1 110. A 111. B 112. C
113. B 114. A 115. C 116. D 117. B 118. B 119. D
120. 1 121. C 122. C 123. C 124. D 125. D 126. 4
127. D 128. B 129. A 130. A 131. C 132. B 133. C
134. C 135. A 136. 4 137. 2 138. 9 139. D 140. B
141. B 142. C 143. D 144 C 145. C 146. B 147. B
148. C 149. B 150. B 151. A 152. C 153. C 154. A
155. D 156. C 157. C 158. B 159. C
1. B 2. B 3. A–PS, B–QR, C–PR, D–S 4. A 5. D

6. BC 7. A 8. 2 9. B 10. 8 11. 4 12. 1
13. 6 14. 4 15. A 16. B, C 17. A 18. D 19. BCD
20. AC 21. 5 22. 01.50 23. D 24. BC 25. C

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CONTENT

1. Nomenclature of organic compounds 04 – 11

3. General Organic Chemistry 22 – 37

6. Aromatic Compound 89 – 121

7. Alcohols & Ethers 122 – 135

8. Grignard Reagent 136 – 144

9. Carbonyl Compound 145 – 168

10. Carboxylic Acid and its derivative 169 – 185

11. Biomolecule & Polymer 186 – 214

1. Of the following compounds which has a wrong IUPAC name - [AIEEE-2002]

2. The IUPAC name of CH3COCH(CH3)2 is – [AIEEE-2003]

3. The IUPAC name of the compound [AIEEE-2004]

(A) 3,3 -dimethyl-1-hydroxy cyclohexane (B) 1, 1 – dimethyl–3– hydroxy cyclohexane

4. The IUPAC name of the compound shown below is - [AIEEE-2006]

(A) 6-bromo-2-chlorocyclohexene (B) 3-bromo-1-chlorocyclohexene

5. The IUPAC name of [AIEEE-2007]

(A) 1, 1-diethyl-2-dimethylpentane (B) 4, 4-dimethyl-5, 5-diethylpentane

7. The IUPAC name of neopentane is : [AIEEE -2009]

8. The IUPAC name of compound is :- [AIEEE -2012 (Online)]

(A) 1, 2-Epoxy propane (B) Propylene oxide

9. The IUPAC name of the followig compounds is : [AIEEE -2012 (Online)]

(A) (Z) – 5– hepten – 3 – yne (B) (Z) – 2– hepten – 4 – yne

10. Aspirin is known as : [AIEEE -2012]

(C) 2-chloro-1-methyl 1-4-nitribenzene

16. The IUPAC name for the following compound is : [JEE-Main-2020]

18. The IUPAC name of the following compound is : [JEE-Main-2020]

(1) 2-nitro-4-hydroxymethyl-5 amino benzaldehyde

[JEE-Mains (26-Feb_Shift -2)2021]

20. Mesityl oxide is a common name of : [JEE-Mains (17-March_Shift -1)2021]

21. The number of sigma bonds in [JEE-Mains (25-July_Shift -1)2021]

22. The IUPAC name of ethylidene chloride is : [JEE-Mains (25-Jun-Shift-1)2022]

(A) 3,3,3-trimethyl-1-propene (B) 1,1,1-trimethyl-2-propene

2. Write the IUPAC name of CH3CH2CH = CHCOOH [JEE 1986]

3. The IUPAC name of the compound CH2=CH–CH(CH3)2 is : [JEE 1987]

5. Write I.U.P.A.C name of following : [JEE 1990]

(a) Me = methyl group

6. Write IUPAC name of succinic acid. [JEE 1994]

7. The IUPAC name of C6H5COCl is [JEE 2006]

8. The IUPAC name of the following compound is [JEE 2009]

(A) 1-chloro-4-methylbenzene (B) 4-chlorotoluene

(A) (B) (C) (D)

8. A 9. D 10. A 11. D 12. C 13. B 14. C

15. D 16. D 17. D 18. D 19. A 20. B 21. 10

22. D 23. C 24. 0 or 1 25. B

Previous Year | JEE Advanced

Pent-2-en-1-oic acid or Pent-2-enoic acid

6. Butane 1,4 dioic acid 7. C 8. B 9. C 10. 6

11. ACD 12. AB 13. D

1. Which types of isomerism is shown by 2,3–dichlorobutane ? [AIEEE-2005]

4. Which one of the following conformations of cyclohexane is chiral ? [AIEEE-2007]

5. The absolute configuration of

(A) R, R (B) R, S (C) S, R (D) S, S

6. The alkene that exhibits geometrical isomerism is : [AIEEE-2009]

9. Identify the compound that exhibits tautomerism [AIEEE-2011]

(A) III (B) I (C) and I III (D) and V

(A) Two (B) Four (C) Six (D) Zero

[JEE Mains Online, 2020]

17. Among the following compounds, geometrical isomerism is exhibited by :

CHCl CHCl CHCl CH2