ENTHUSE

IIT CHEMISTRY
ORGANIC CHEMISTRY

STEREO ISOMERISM

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 EXERCISE#I (MAINS ORIENTED)
1. Compound CH2Cl2 contain :
(A) Plane of symmetry (B) Centre of symmetry
(C) Axis of symmetry (D) Both (A) & (C)
2. If 'X' is total number of plane of symmetry, 'Y' is total number of two fold axis of symmetry
and 'Z' is total number of four fold alternate axis of symmetry present in CH4 . Then find the
value of ( X + Y – Z).
(A) 3 (B) 4 (C) 5 (D) 6
3. How many stereoisomers of the following molecule are possible ?
HOOC.CH=C=CH.COOH
(A) Two optical isomers (B) Two geometrical isomers
(C) Two optical and two geometrical isomers (D) None
4. The number of cis-trans isomer possible for the following compound.

CH CH CH C CH

(A) 2 (B) 4 (C) 6 (D) 8

I H

N OH
5. has ‘x’ chiral centre then find the value of x :
D
Cl
S
O

(A) 7 (B) 8 (C) 6 (D) 5

6. The number of optically active compounds in the isomers of C4H9Br is.
(A) 1 (B) 2 (C) 3 (D) 4

7. Compound have CH3

H
H Cl
Cl H
H
CH 3
(A) Plane of symmetry (B) Centre of symmetry
(C) Axis of symmetry (D) None
CHO
Br Cl
8. F H
COOH
Configuration of compound is :
(A) 2S, 3S (B) 2R , 3S (C) 2R , 3R (D) 2S , 3R

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9. Which of the given conformation of n-butane is chiral ?
(A) Fully Eclipsed (B) Anti
(C) Gauche (D) None of these

10. Minimum molecular weight of a hydrocarbon containing minimum number of C-atom to show optical
isomerism.
(A) 100 (B) 80 (C) 68 (D) 70

11. Compounds which can show both optical as well as geometrical isomerism :

(A) (B)

(C) (D)

12. Which of the following will not show optical isomerism :

Me Me Me CH3
(A) (B) (C) (D)
H Cl H
Me

13. Optical & geometrical isomerism both can be shown by

(A) (B)

(C) (D)

14. Which of the following will not show optical isomerism.

(A) Cl – CH = C = C = CH–Cl (B) Cl – CH = C= C=C = CH – Cl

H
COOH Cl H
H OH
(C) H OH (D)
COOH Me Cl
Me
15. Meso-tartaric acid and d-tartaric acid are :
(A) Positional isomers (B) Enantiomers (C) Diastereomers (D) Racemic mixture

16. The two compounds given below are :

D Cl
H Br I H
H Cl D H
I Br
(A) Enantiomers (B) Diastereomers (C) Optically inactive (D) Identical

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17. Which of the following combinations amongst the four Fischer projections represents the same absolute
configurations?
CH 3 OH CH CH2 H
H OH H CH 3 CH3 OH HO CH CH2
CH CH2 CH CH2 H
CH3
(I) (II) (III) (IV)
(A) (II) and (III) (B) (I) and (IV) (C) (II) and (IV) (D) (III) and (IV)
18. The S-ibuprofen is responsible for its pain relveing property. Which one of the structure shown is S-
ibuprofen :

(A) (B)

(C) (D)

19. Which of the following is a 'threo' isomer :

CH 3 CHO COOH COOH
H OH HO H H Cl H NH2
(A) H OH (B) H OH (C) H OH (D) H OH
CH 2OH CH 2 OH CH3 CH 3
20. Number of possible stereoisomers of glucose are :
(A) 10 (B) 8 (C) 16 (D) 20
21. Which of the following is not D sugar :

CHO CHO
H OH H OH
HO H HO H
(A) H OH (B) H OH
HO CH 2 H H CH 2 OH
OH OH

CH 2OH
H
OHC OH C O
HO H HO H
(C) H OH (D) H OH
HO CH 2 OH H OH
H CH 2OH

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 STEREO ISOMERISM
22. Number of chiral centres in [X] & [Y] is a & b respectively. The value of (a–b) is :

O
Me OH

[X] = [Y] =
O Cl Br
Cl
(A) 1 (B) 2 (C) 3 (D) 4
23. For the newman projection of n-butane, which of the following pair(s) of (X,Y) is/are
possible? H
H H

H X
Y
(A) (CH3, CH3) (B) (CH3, Et) (C) (H, Et) (D) (Et, H)

24. How many stereoisomers can exist for the following acid.
H–C(OH).CO2H
H–C.CO2H
H–C(OH).CO2H
(A) Two (B) Four (C) Eight (D) Six
25. Incorrect relationship between given compounds are

OH OH

H H
(A) Both are geometrical isomers (B) Both are stereo isomers
(C) Both are enantiomers (D) Both are diastereomers
26. Identify meso compound.

CO 2H
Cl CH3
Me Me CO 2H
(A) HO 2 C CO 2H (B) (C) HO 2 C (D)
Cl Cl
CO 2H
27. A pure sample of 2-chlorobutane shows rotation of PPL by 30° in standard conditions. When above
sample is made impure by mixing its opposite form, so that the composition of the mixture becomes
87.5% d-form and 12.5% l-form, then what will be the observed rotation for mixture.
(A) – 22.5° (B) + 22.5° (C) + 7.5° (D) – 7.5°

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 STEREO ISOMERISM
28. When an optically active compound is placed in a 10 dm tube is present 20 gm in a 200 ml solution
rotates the PPL by 30°. Calculate the angle of rotation & specific angle of rotation if above solution is
diluted to 1 Litre.
(A) 16° & 36° (B) 6° & 30° (C) 3° & 30° (D) 6° & 36°
29. Identify % optical purity if 6 gm (+)-2-butanol is mixed with 2 gm (–)-2-butanol.
(A) 50 % (B) 66.6 % (C) 33.3 % (D) 75 %
30. A mixture of d and l, 2-bromobutane contain 75% d-2-bromobutane. Calculate enantiomeric excess.
(A)75% (B) 25% (C) 50% (D) 100%
31. Which of the following is example of meso compound?

O O
NH
(A) HN NH (B) HN NH (C) O O (D)
NH
O O
32. Which of the following has C2 & C3 axis of symmetry?
Cl
N
(A) H H (B) H2CCl2 (C) H3C–Cl (D) B
H Cl Cl

33. Which of the following pair of cyclohexane is flexible ?

(A) Chair (B) Twist boat
(C) Half boat (D) All of these

COOH COOH
H OH
34. H H OH compound related as :
H OH
OH
CHO
CHO
(A) Enantiomers (B) Conformation (C) Identicle (D) Diastereomers
35. For the given configuration :

COOH H
Cl H COOH Cl
H COOH Cl Cl Cl
H Cl Cl Cl H H HOOC
COOH COOH COOH COOH

(I) (II) (III) (IV)

Which of the compound/configuration are optically active :
(A) I (B) II (C) III (D) IV

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 STEREO ISOMERISM
EXERCISE-II (JEE Advanced Oriented Level-II)
1. Molecular formula C5H10O can have :
(A) 6–Aldehyde, 4–Ketone (B) 5-Aldehyde, 3-Ketone
(C) 4-Aldehyde, 3-Ketone (D) 5-Aldehyde, 2-Ketone
Me
2. Statement 1: H Et is a chiral resolvable molecule.
Cl
Me
Statement 2: H Et is non-superimposable on its mirror image.
Cl
(A)Statement–1 is true, Statement–2 is true; Statement–2 is not the correct explanation of Statement–1
(B)Statement–1 is true, Statement–2 is true ; Statement–2 is the correct explanation of Statement–1
(C)Statement–1 is true, Statement–2 is false
(D)Statement–1 is false, Statement–2 is true
3. Total number of stereoisomer of following compounds are respectively
CH3 – CH = CH – CH(OH) – CH = CH – CH3 ; CH3 – CH(OH) – CH = CH – CH(OH)–CH3
(A) 4, 6 (B) 8 (C) 6,6 (D) 8, 8
4. Which of the following compounds are optically active ?
(A) CH3– CH(OH) – CH2– CH3 (B) H2C=CH – CH2 – CH=CH2
HOOC NO 2
H Cl
(C) C C C (D)
Cl H
NO 2 COOH
5. Which out the following are Non-resolvable :
H H
H H Br H H COOH
(A) (B) (C) COOH (D) COOH
Br Br H Br COOH H
6. Which of the following statements is/are not correct :
(A) Metamerism belongs to the category of structural isomerism
(B) Tautomeric structures are the resonating structures of a molecule
(C) Keto form is always more stable than the enol form
(D) Geometrical isomerism is shown only by alkenes
7. Identify compounds which are not meso :
Br
Cl CH3
Me Me COOH (D)
(A) HOOC COOH (B) (C) HOOC
Br
Cl Cl
8. Which of the following statements for a meso compound is/are correct :
(A)The meso compound has either a plane or centre of symmetry or both
(B)The meso compound is optically inactive due to internal compensation.
(C)The meso compound is achiral
(D)The meso compound is formed when equal amounts of two enantiomers are mixed

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 STEREO ISOMERISM
9. Compound A having molecular formula C2Cl2Br2. A having plane of symmetry (POS), centre of symmetry
(COS) & C2 axis of symmetry, A is :
Cl Cl
Br Cl Cl Cl Cl Br
(A) Br C C (B) Br C C (C) Br C C (D)
Cl Br Cl
Br Br

10. Among the following the non- resolvable compound is/are :

CH3
H3 C CH3 Br
(A) C C (B)
Cl Br H
CH3

(C) P (D) N
H3 C H H3C Br
Br H

COO H
11. Compound H NH2 is/are ?
HO H
CH3
(A) (2R, 3S), L (B) L, Erythreo (C) Threo , D (D) (2R, 3S), D
12. Relation between compounds are :
COOH CHO COOH
H OH HO COOH
H OH
CHO H CHO
(A) I & II = Enantiomers (B) II & III = Enantiomers
(C)I & II = Identical (D) II & III = Identical

13. Compare the stability of following conformations of 1,4-Dimethyl cyclohexane :

CH3 H
H CH3 H CH3
H3 C H
H H
H H
(Q) H H
(P) H (R) H

(A) P = Q > R (B) P > Q > R (C) Q > P > R (D) R > P = Q

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 STEREO ISOMERISM
14. Identify correct relation between pair of compounds ?

Me Me

(A) & Diastereomers

Me Me

Me Me
H OH H OH
(B) H OH & Identical
Me OH H
Me

Me Me
H Me Cl
H
(C) & Diastereomers
H OH H OH
Cl Me
Me Me
(D) H OH & HO H Enantiomers
Et Et

15. Column-I Column-II

H CH3 H
CH 2 OH H3 C
CH 2 NH 2
(A) & (P) Structural
NH2 OH

CH3 Cl
H Cl H CH3
(B) & (Q) Identical
Et Et

CH3 H
H OH H3 C Et
(C) & (R) Enantiomers
Et OH

H5C 2 H5C 2
(D) & (S) Diastereomers
HO H H OH

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 STEREO ISOMERISM
16. Column-I Column-II
Me CH CH CH3 H CH3
(A) (P) Geometrical isomers
H H CH3 CH CH H
Me CH 2 CH CH2 Me H
(B) (Q) At least one of the compound
can show Geometrical
H H H CH CH CH3 Isomerism

(C) (R) At least one of the compound

can show Optical Isomerism

(D) CH2=CH–CH=CH–CH3CH3–CH=C=CH–CH3 (S) Positional isomers

17. Column-I Column-II

COOH COOH
(A) A pair of metamer (P) H OH ; H OH
HO H H OH
COOH COOH
(B) Tautomerism (Q) CH3OC3H7 ; C2H5OC2H5
CH3 CH3
(C) A pair of geometrical isomer (R) H OH ; HO H
COOH COOH
H3 C CH3 H3 C H
(D) A pair of distereomers (S) C C ; C C
H H H CH3

O
(E) A pair of optical isomer (T) CH3 CH2 CH2 CH2 CH ;
CH3 CH2 CH CH OH

Subjective Type Questions:

18. What is number of chiral centres present in Diosgenen is :
CH3
CH3 O
CH3
H3 C O Progesterone
Several Step Human female Harmone
HO
Diosgenin

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 STEREO ISOMERISM

19. Calculate the total number of chrial carbon atoms in.

(i) (ii)

20. Total number of isomers of bromochlorofluoroiodo propadiene is ?

21. Find out the total number of cyclic isomers of C6H12 which are optically active?
22. How many of the given compounds are chiral :
OH

(i) (ii) (iii) (iv)

OH Br

COOH
CN Cl COOH
(v) (vi) (vii)
H OH
CN H

H Cl
(viii) . (ix)
Br H

23. With reasons, state whether each of the following compounds I to VIII is chiral

Cl Cl

H H
(I) Cl (II) H (III)
HO 2 C CO 2 H
H Cl

Ph

Cl CO 2H O O
(IV) C C C (V) (VI)
Cl Me
CO 2H

Me
(VII) S O
Ph

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 STEREO ISOMERISM

24. How many cyclopentane structures (including stereo) are possible for C7H14.

25. The number of diastereoisomers (excluding optical) for 1-bromo-2-chloro-3-iodocyclopropane.

26. Identify total number of stereoisomers for the following compound :

CH3 CH CH CH CH CH3
HO Cl

27. How many of the given molecule / species are chiral :

Cl
Cl Cl
(i) (ii) (iii)
OH
Br OH

OH Br
COOH CH3
(iv) HOOC (v) (vi) H C
3
OH F F

(vii) (viii) (ix) CH4

28. For the compound '5-Methyl hept-3-en-2-one' if :

(i) Total number of stereoisomers possible is 'x'
(ii) Total number of enantiomeric pairs possible is 'y'
Then represent your answer as 'xyx'
[For example x = 1, y = 2 then answer is 121]

29. How many of following has same number of stable conformation ?

(1) Ethane (2) Propane (3) Butane (4) Isobutane
(5) Neopentane (6) Neohexane (7) Methanol (8) Dimethylether
(9) Ethyl Chloride

30. How many of following has only three stable conformation ?

(1) 2,2-dimethylbutane (2) isopropanol (3) 2-chlorobutane
(4) Pentane (5) (+) 2,3-Dibromobutane (6) Ethanol

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 STEREO ISOMERISM

EXERCISE-III (JEE ADVANCE ORIENTED LEVEL-II)

1. Observe the given compounds and answer the following questions.
CO 2 H CO 2 H CO 2 H CO2 H CO 2 H
H OH H OH HO H HO H H OH
H OH HO H H OH HO H HO H
H OH H OH H OH HO H HO H
CO 2 H CO 2 H CO 2 H CO2 H CO 2 H
(I) (II) (III) (IV) (V)
(i) Which of the above formulae represent identical compounds ?
(A) I and II (B) I and IV (C) II and IV (D) III and IV
(ii) Which of the above compounds are enantiomers ?
(A) II and III (B) III and IV (C) III and V (D) I and V
2. Which of the following option is correct regarding the given compounds :
CH3 H H H
C C C C C C
H CH3 CH3 CH3
(A) Both are identical (B) Both are optically inactive
(C) Both are optically active (D) Geometrical isomer
3. Which of the following pairs of compound is/are identical ?
Br H CH 3 I
F Br I
Br HF Cl
H
Cl
H CH3
(A) H (B) H I
F Br
F I H
H

H Br
Cl CH3
H
H H H Cl
CH3 Cl H
Cl CH H Cl
(C) 3 (D) Br I I
H
H
CH3
Cl H
Multiple Correct Type:
4. Which of the following statements is/are not correct for D-(+) glyceraldehyde :
(A)The symbol D indicates the dextrorotatory nature of the compound
(B)The sign(+) indicates the dextrorotatory nature of the compound
(C)The symbol D indicates that hydrogen atom lies left to the chiral centre in the Fischer projection
diagram
(D)The symbol D indicates that hydrogen atom lies right to the chiral centre in the Fischer projection
diagram
5. Which of the following are correct representation of L-amino acids :

COOH NH2 OH
H COOH
(A) H2 N H (B) H
C C
COOH (C) (D)H C
3
NH2
CH 2 OH CH 2 OH H

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 STEREO ISOMERISM
6. Identify relation between these two compounds :

Cl Br

Br Cl
(A) Homomers (B) Enantiomers (C) Diastereomers (D) Positional Isomers

Comprehension Type:
Paragraph for Q.No. 7 to 9
Four compounds are given below 'S' is a stereoisomer of P.
Me
Et
Cl H
H Cl
(P) (Q) Cl H
Cl H
Et Me

Me
H Cl H
Et Cl
(R) H (S)
Me X Y
Cl Z
7. P & Q are related as :
(A) Identical (B) Enantiomer (C) Diastereomer (D)Positional isomerism

8. If Q and S are enantiomer then which is/are correctly matched :

(A) X=H (B) Y=Cl (C) Z=Et (D) X=Cl

Paragraph for Q.No. 9 to 11

S(+) Mono sodium Glutamate (MSG) is a flavour enhancer used in many foods. Fast foods often
contain substantial amount of MSG and is widely used in Chinese food. If one mole of above MSG was
placed in 845 ml solution and passed through 200 mm tube, the observed rotation was found to be +
9.6°.
– +
COO Na
–
OOC–CH2–CH2–C
+
NH3 H

9. Find out the specific rotation of (–) MSG :

(A) + 24° (B) +56.8º (C) –48° (D) None of these

10. Find out the approximate percentage composition of (–) MSG in a mixture containing (+) MSG and
(–) MSG whose specific optical rotation is –20°:
(A) 83.3% (B) 16.7% (C) 91.6% (D) 74%

11. If 33.8 g of (+) MSG was put in 338 ml solution and was mixed with 16.9g of (–) MSG put in 169 ml
solution and the final solution was passed through 400 mm tube. Find out observed rotation of the final
solution :
(A) +1.6° (B) +4.8° (C) +3.2° (D) None of these

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 STEREO ISOMERISM
Paragraph for Q.No. 12 to 13
Among the following structures?

O O COOH
NH2 H OH
(I) N N (II) (III) HO H
R R NH2 COOH

Cl
Cl

H Cl
(IV) (V) (VI)
Cl H
Cl Cl

COOH
F Cl H OH
(VII) C=C=C=C (VIII) H OH
I Br
COOH
12. Optically active compound is
(A) III (B) IV (C) V (D) VII
13. Which of the following will not show optical isomerism
(A) I (B) II (C) V (D) VIII
Matrix Match Typed
14. Column-I Column-II
(Compounds) (Relation)
CH2OCH3 OCH2CH3
Me Me Me H
(A) H H (P) Metamers
H H H Me

D D D D

(B) (Q) Functional Isomer

OCH3 CH2OH

D D D D

(C) (R) Geometrical isomer

14
CH3 CH3
H D D H
(D) D H H D (S) Enantiomer
CH3 CH3
14
(T) Diastereomer

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 STEREO ISOMERISM
15. Match List-I, II, III with each other :
List-I List-II List-III
CH3 H CH3
Br H
(A) HO H (1) HO C C H (i) (2R, 3R)
CH3 CH3 Br

CH3 H
CH3
HO H
(B) Br (2) Br C C OH (ii) (2S,3S)
H
CH3 CH3
H
CH3 CH3 CH3
H OH
(C) Br H (3) OH C C Br (iii) (2S,3R)
CH3 H H

CH3 H
Br
HO H H C C OH
(D) H Br (4) (iv) (2R,3S)
CH3 H3C CH3

Subjective Type:
16. In what stereoisomeric forms would you expect the following compounds to exist ?

(a) EtCH(CO2H)Me (b) MeCH(CO2Et)CO2H (c)

O
H H
(d) (e) C=C=C=C (f) Et(Me)C=C=C(Me)Et
H H

Ph CO2H I CH3
Cl
(g) (h) (i) (j) (k)
Ph CO2H O
Br H
17. Calculate the number of Benzenoid isomers possible for C6H3ClBrI.

18. What are the relationships between the following pairs of isomers ?
Br CO H Br CO H CO Me
2 2 2

(a) and (b) and CO 2Me

Br CO2H Br CO2H Br Br
Br Br
(c) and (d) and

CHO CHO
H OH HO H CHO CH2OH
H OH H OH H NH 2 H OH
(e) H OH and HO H (f) HO H and H NH2
CH2OH CH2OH CH2OH CHO

H Cl
H H H CH3
H H HO OH
(g) Cl Ph and H (h) and
Ph HO OH H H
CH3 H
(i) and

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 2H2
19. X pt
Find out total number of structures of X.

20. Calculate the number of chiral center in the molecule Ethyl 2,2-dibromo-4-ethyl-6-methoxy
cyclohexane carboxylate.

21. Calculate the total number of stereoisomers possible for

Cl
Cl Cl
H CH=CH–CH3
(i) (ii) Cl (iii) C=C=C
CH=CH–CH3
Cl Cl
Cl

COOH
CHO
CHOH
CHOH
CHOH
(iv) CHOH (v) (vi)
CHOH
CH2OH O COOH

(vii) CH3–CH–CH=CH CH=CH–CH–CH3 (viii)

Cl Me
CH3 COOH

NH2
N N O
O
(ix) EtO–P N N (x) (xi)
OH
OEt

22. Find the total number of stable conformation having non zero dipole moment for
meso-2,3-dichloro butane

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 EXERCISE-IV (A) (JEE MAINS)
1. Recemic mixture is formed by mixing two : [AIEEE-2002]
(A) Isomeric compounds (B) Chiral compounds
(C) Meso compounds (D) Enantiomers with chiral carbon
2. Following types of compounds I and II [AIEEE-2002]
(I) CH3CH=CHCH3
(II) CH3 CH OH, are studied in terms of isomerism in
CH2CH 3
(A) Chain isomerism (B) Position isomerism
(C) Conformers (D) Stereo isomerism
3. Among the following four structures I to IV [AIEEE-2003]
H
C2H5 CH C3H7 C2H5 C CH C2H5 H C C2H5 CH C2H5
CH3 O CH3 H CH3
(I) (II) (IV) (IV)
It is true that
(A) All four are chiral compounds (B) Only I and II are chiral compounds
(C) Only III is a chiral compound (D) Only II and IV are chiral compounds
4. Which of the following will have a meso-isomer also [AIEEE-2004]
(A) 2–chlorobutane (B) 2,3–dichlorobutane
(C) 2,3–dichloropentene (D) 2–hydroxy propanoic acid
5. Amongst the following compounds, the optically active alkane having lowest molecular mass is
CH3
(A) CH3—CH2—C =CH (B) CH3 CH2 CH CH3
H
(C) CH3 C (D) CH3—CH2—CH2—CH3
C2H5

6. Which of following compounds is not chiral [AIEEE-2005]

(A) 1–chloropentane (B) 2–chloropentane
(C) 1–chloro–2–methyl pentane (D) 3–chloro–2–methyl pentane
7. Of the five isomeric hexanes, the isomer which can give two monochlorinated compounds is:
(A) 2-methyl pentane (B) 2,2–dimethyl butane
(C) 2,3–dimethyl butane (D) n-hexane [AIEEE-2005]
8. Which types of isomerism is shown by 2,3–dichloro butane [AIEEE-2005]
(A) Structural (B) Geometric (C) Optical (D) Diastereo
9. The absolute configuration of is: [AIEEE-2008]
HO2C CO2H

HO H H OH
(A) S, S (B) R, R (C) R, S (D) S, R

10. The number of stereoisomers possible for a compound of the molecular formula
CH3–CH=CH–CH(OH)–Me is [AIEEE-2009]
(A) 4 (B) 6 (C) 3 (D) 2

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11. Out of the following, the alkene that exhibits optical isomerism is : [AIEEE-2010]
(A) 2-methyl-2-pentene (B) 3-methyl-2-pentene
(C) 4-methyl-1-pentene (D) 3-methyl-1-pentene

12. The optically inactive compound from the following is : [JEE-MAIN 2015]
(A) 2-chloropropanal (B) 2-chlorobutane
(C) 2-chloro-2-methylbutane (D) 2-chloropentane

13. The absolute configuration of : [JEE-MAIN 2016]

CO2H
H OH
H Cl
CH3
(A) (2R, 3R) (B) (2R, 3S) (C) (2S, 3R) (D) (2S, 3S)
14. Which of these factors does not govern the stability of a conformation in acyclic compounds ?
[JEE MAIN-2019]
(A) Steric interactions (B) Torsional strain
(C) Electrostatic forces of interaction (D) Angle strain
15. In the following skew conformation of ethane, H’–C–C–H” dihedral angle is:
[JEE MAIN-2019]

(A) 58º (B) 151º (C) 120º (D) 149º

16. Which of the following compounds will show the maximum ‘enol’ content? [JEE MAIN-2019]
(A) CH3COCH2COCH3 (B) CH3COCH3
(C) CH3COCH2COOC2H5 (D) CH3COCH2CONH2

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 EXERCISE-IV (B) (JEEAdvanced)
H3C H
C=C H
1. The H C C shows: [IIT JEE - 1995]
3
COOH
CH3
(A) Geometrical isomerism (B) Optical isomerism
(C) Geometrical & optical isomerism (D) tautomerism
2. How many optically active stereoisomers are possible for butane –2,3–diol : [IIT JEE - 1997]
(A) 1 (B) 2 (C) 3 (D) 4
3. The number of possible enantiomeric pairs that can be produced during monochlorinationof 2–methyl
butane is : [IIT JEE - 1997]
(A) 2 (B) 3 (C) 4 (D) 1
4. Identify the pairs of enantiomers and diastereomers from the following compounds I, II and III
[IIT JEE - 2000]
CH3 CH3 CH3
H OH HO H HO H
HO H HO H H OH
CH3 CH3 CH3
I II III

5. Which of the following compounds exhibits stereoisomerism [IIT JEE - 2002]

(A) 2–Methylbutene–1 (B) 3–Methylbutyne–1
(C) 3–Methylbutanoic acid (D) 2–Methylbutanoic acid
6. On monochlorination of 2-methylbutane, the total number of chiral compounds formed is :
[IIT JEE - 2004]
(A) 2 (B) 4 (C) 6 (D) 8
7. Statement -I : Molecules that are not superimposable on their mirror images are chiral
Because
Statement -II :All chiral molecules have chiral centres. [IIT 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.
8. The correct statement(s) concerning the structures E, F and G is (are) [IIT JEE - 2008]
H3C O OH CH3
H3C H3C
H3C CH3 H3C CH3 H3C OH
(E) (F) (G)
(A) E, F and G are resonance structures (B) E, F and E, G are tautomers
(C) F and G are geometrical isomers (D) F and G are diastereomers
9. The correct statement(s) about the compound given below is (are) [IIT JEE - 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

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10. The correct statement(s) about the compound H3C(HO)HC – CH = CH – CH(OH)CH3 (X) is (are):
[IIT JEE - 2009]
(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
11. In the Newman projection for 2,2–dimethylbutane [IIT JEE - 2010]
X

H3C CH3

H H
Y
X and Y can respectively be
(A) H and H (B) H and C2H5 (C) C2H5 and H (D) CH3 and CH3
12. Which of the given statement(s) about N,O,P and Q with respect to M is (are) correct ?
[IIT JEE - 2012]
HO HO C1 CH3 CH3
H H
H OH H OH HO H
C1 CH3
HO H HO
H OH H
HO H HO H
CH3 Cl CH3
C1 C1
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
13. The total number(s) of Stable conformers with non-zero dipole moment for the following compound is
(are) [IIT JEE - 2014]
C1
Br CH3
Br C1
CH3
14. The total number of stereoisomers that can exist for M is : [IIT JEE - 2015]

H3C CH3

H3C O
M
15. In the following monobromination reaction, the number of possible chiral products is
[IIT JEE - 2016]
CH2CH2CH3
Br2(1.0 mole)
H Br
300ºC
CH3
(1.0 mole)
(enatiomerically pure)

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Q.16 For the given compound X, the total number of optically active stereoisomers is

[IIT JEE - 2018]

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 ANSWER KEY
EXERCISE#I (MAINS ORIENTED)
1. D 2. D 3. A 4. A 5. A
6. B 7. B 8. D 9. C 10. C
11. C 12. D 13. C 14. A 15. C
16. A 17. C 18. D 19. B 20. C
21. B 22. B 23. ACD 24. B 25. C
26. A 27. B 28. B 29. A 30. C
31. A 32. D 33. B 34. A 35. B
EXERCISE-II (JEE ADVANCE ORIENTED LEVEL-II)
1. B 2. B 3. A 4. ACD 5. AC
6. BCD 7. BCD 8. BC 9. C 10. ABD
11. CD 12. AD 13. C 14. ABCD
15. (A)P ; (B)R ; (C)Q ; (D)R
16. (A)P,Q ; (B)Q,S ; (C)Q,R,S ; (D)Q,R,S
17. (A)Q; (B)T; (C)S; (D)P,S; (E)P,R;
18. 11 19. (i) 6, (ii) 8 20. 6 21. 8 22. 6
23. Achiral : I, III , IV ; chiral : II,V, VI, VII 24. 8 25. 4
26. 8 27. 3 28. 424 29. 8 30. 3
EXERCISE-III (JEE ADVANCE ORIENTED LEVEL-II)
1. (i) B; (ii) C 2. C 3. C 4. AD 5. ACD
6. C 7. B
8. CD
9. D 10. C 11. C 12. A 13. C
14. (A)P ; (B)Q ; (C)R,S ; (D)S
15. (A)-4-iii ; (B)-3-iv ; (C)-2-ii ; (D)-1-i
16. Optical : a,b,c,d,f,g,i,j,k ; Geometrical isomer : c,g,j ; None : e, h
17. 10
18. (a) Enantiomers, (b) Enantiomers, (c) Geometrical isomers & Diastereomers,(d) Positional, (e)
Optical, (Diastereomers), (f) Diastereomers(g) Enantiomers, (h) Identical, (i) Geometrical isomers
(Diastereomers)
19. 7 20. 3
21. (i) 2 (ii) 9 (iii) 4 (iv) 4 (v) 0, (vi) 4 (vii) 25, (viii) 24, (ix) 2, (x) 4, (xi) 3
4
22. 2
EXERCISE-IV (A) (JEE MAINS)
1. D 2. D 3. B 4. B 5. C
6. A 7. C 8. C 9. B 10. A
11. D 12. C 13. C 14. D 15. D
16. A

EXERCISE-IV (B) (JEEADVANCED)

1. B 2. B 3. A
4. Enantiomers - I and III ; Diastereomers - I & II and II & III
5. D 6. B 7. C 8. BCD 9. AD
10. AD 11. BD 12. ABC 13. 3 14. 2
15. 5 16. 7

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