1

Ummeed NEET 2025

General Organic Chemistry (GOC) Workbook
General Introduction: Electronegativity & Electron Density:
Electronegativity:
The tendency to attract an electron pair towards itself in a
covalently bonded bond.

Basics of any Organic Reaction:

Electron Density:

Organic Chemistry ka PANJA:

Example: S- > S > S+

 2

Electronic displacement Effect: Inductive Effect:

Permanent Effect Temporary Effect 1. Operate to sigma bond.
1. Inductive Effect Electronic Effect 2. Partial charge development.
2. Mesomeric Effect 3. Distance dependent effect.
3. Hyperconjugation 4. Can be neglected after 3rd carbon atom.

Power of (+I) Inductive Effect:

- - - -
1. -CH 2 > − NH > − O > − CO O > 30 R > 20 R >10R > − Me

2. - T > − D > − H
3. - CH 3 < − SiH 3 < − GeH 3
C.Q. 1. Which among the following is incorrect statement?
(JEE Mains 2024)
(1) Electromeric effects dominate over inductive
effect.
(2) The electromeric effect is temporary effect.
(3) The organic compound shows electromeric
effect in the presence of the reagent only.
(4) Hydrogen ion (H+) shows negative electromeric
effect.
Solution.
 3

Power of (-I) Inductive Effect: C.Q. 2. Which of the following is correct with respect to –I
+ + + + effect of the substituents? (R = alkyl) (NEET 2018)
− NF3  − NR3  − SR 2  − NH3  −NO2  −SO3H  −CN (1) – NH2 < – OR > – F
(2) – NR2 < – OR < – F
> –CHO > –COOH > –F > – Cl > –Br > –I > –OR > –OH (3) – NR2 > – OR > – F
(4) – NH2 > – OR > – F
> –C  CH > –NH2 > –Benzene > Ene > H Solution.

Applications of Inductive Effect:

1. To compare acidic strength of Aliphatic carboxylic
acids.

Q. Draw direction of the effect.

C.Q. 3. The correct sequence of acidic strength of the

following aliphatic acids in their decreasing order is:
CH3CH2COOH, CH3COOH, CH3CH2CH2COOH,
HCOOH (JEE Mains 2024)
(1) HCOOH > CH3COOH > CH3CH2COOH >
CH3CH2CH2COOH
(2) HCOOH > CH3CH2CH2COOH >
CH3CH2COOH > CH3COOH
(3) CH3CH2CH2COOH > CH3CH2COOH >
CH3COOH > HCOOH
(4) CH3COOH > CH3CH2COOH >
CH3CH2CH2COOH > HCOOH
 4

Solution. C.Q. 5. In which of the following compounds the hydroxylic

proton is most acidic?

(1)

(2)

(3)

C.Q. 4. The correct decreasing order for acid strength is: (4)
(JEE Mains 2019)
(1) CNCH2COOH > O2NCH2COOH > FCH2COOH
> ClCH2COOH Solution.
(2) FCH2COOH > NCCH2COOH > NO2CH2COOH
> ClCH2COOH
(3) NO2CH2COOH > NCCH2COOH > FCH2COOH
> ClCH2COOH
(4) NO2CH2COOH > FCH2COOH > CNCH2COOH
> ClCH2COOH
Solution.

3. To compare stability of carbocations

2. To compare acidic strength of Alcohols

 5

C.Q. 6. Arrange the following in increasing order of C.Q. 7. The order of decreasing stability of the anions is:
stability: (CH3 )3 C− (CH3 ) 2 CH − CH 3CH 2−
 (I) (II) (III)
(A) (CH3 )2 C− CH 2CH3
(1) I > II > III

(B) (CH3 )3 − C (2) III > II > I

(3) II > I > III
(C) (CH3 ) 2 − C H (4) I > II > III
 Solution.
(D) CH3 − C H 2

(E) C H3 (NEET 2013)
(1) E<D<C<B<A
(2) E<D<C<A<B
(3) D<E<C<A<B
(4) A<E<D<C<B
Solution.

5. To compare stability of free radicals

4. To compare stability of carbanions

C.Q. 8. The stability of given free radicals in decreasing order

is:
• •
(i) CH3 − C H 2 (ii) CH3 − C H − CH3
•
•
CH 3 − C − CH 3
(iii) | (iv) C H3
C H3
(1) iii > iv > i > ii
(2) i > ii > iii > iv
(3) iii > ii > iv > i
(4) iii > ii > i > iv
 6

Solution. RESONANCE:
Arrow Ghumana Seekh Jaoge
Old definition:
1. When a single Lewis structure cannot explain all the
properties of a molecule.
Then we need more than one such structures.
2. These structures are called Resonating structures (or
canonical form).
3. Resonating structures are hypothetical.
6. To compare Basic Strength of Amines 4. Resonance hybrid is the real structure.

Definition:
Delocalization of π electrons in conjugated system.

C.Q. 9. Which is the most basic among the following?

(1) CH3CH2NH2
(2) ClCH2CH2NH2
(3) O2NCH2CH2NH2
(4) –OCH2CH2NH2
Solution.
 7

Types of Conjugation: C.Q. 10. Which of the following compounds have not
delocalized electrons?
(1) CH2 = CH – C ≡ CH
(2) CH2 = C = CH2

(3)

(4) CH3–COOH
Solution.

OP Points:
1. Hypothetical concept

2. Intramolecular process

Conditions for Resonance:

1. Molecule should be planner.
3. RS are imaginary concept.

4. RH is real.

2. Conjugated system. 5. Atoms cannot move in resonance.

6. Total number of paired unpaired electrons remain same.

 8

7. Total number of electrons remain the same. 4. Charge separating R.S are less stable.

8. Any structure violating the fundamental rule is not

accepted as RS.

Compare Stability in Pankaj sir’s style:

1. Neutral R.S > Charged R.S

5. Like charges on adjacent position are least stable.

2. Stability of R.S α no. of π bonds

C.Q. 11. The correct stability order of the following

resonance structures of CH3–CH = CH–CHO is:

3. Stability of R.S α Stability of Charge (JEE Mains 2024)

(1) II > III > I (2) III > II > I
(3) I > II > III (4) II > I > III
Solution.
 9

C.Q. 12. Relative stability of the contributing structures is: Extended & Cross Conjugation:

(JEE Mains 2024)

(1) (I) > (III) > (II)
(2) (I) > (II) > (III)
(3) (II) > (I) > (III)
(4) (III) > (II) > (I)
Solution.

Localized & Delocalized lone pairs:

Bond length:

Equivalent Resonance:
1. When P.E of all R.S are equal then R.S are called
equivalent R.S.

2. Contribution of all R.S are same.

 10

Fries Rule: Resonance V/S Mesomeric Effect:

For Resonating structure of Benzenoid compound. • All resonance effect are mesomeric effects. (T/F)
1. Stability α no. of benzenoid ring • All mesomeric effect are resonance effects. (T/F)

Mesomeric Effect:
Definition +M Effect -M Effect

1. Permanent If an atom or group If an atom or group

effect. donate P orbital e-s withdraw P orbital e-s
2. Operate to π to conjugated to conjugated system
2. Two separating benzenoid rings are more stable bond. system (like double (like double bond or
than two fused benzenoid rings. 3. Distance bond or Benzene Benzene Ring
Independent Ring usually). usually).
effect.
4. Actual Charge
Develop.
 11

Identification of +M and –M groups: Comparison Power of +M Group:

1. +M power α extent of overlapping

2. +M due to L.P > +M due to internal conjugation

 12

Comparison Power of -M Group: C.Q. 13. Arrange the following groups in the increasing
order of –M:
(i) –NO2, –COOR, –CHO, –CN, –COR
O O O
(ii) || || ||
− C− F, − C− NH 2 , − C− O −
Solution.

OP Points of Mesomeric Effect:

1. M effect does not operate on meta position.
 13

C.Q. 14. The set of meta directing functional group from the 2. Hydrogen bonding may increase or decrease acidic
following sets is: (JEE Mains 2024) strength.
(1) –CN, –NH2, –NHR, –OCH3
(2) –NO2, –NH2, –COOH, –COOR
(3) –NO2, –CHO, –SO3H, –COR
(4) –CN, –CHO, –NHCOCH3, –COOR
Solution.

C.Q. 15. Among the following compounds (I-III), the

correct order of reactivity towards electrophilic
substitution reaction is: (AIIMS 2012)

(1) II > III > I (2) III < I < II

(3) I > II > III (4) I = II > III
Solution. 3. Ortho effect

C.Q. 16. Which of the following decreases electron density in

benzene ring through –M effect?
(1) –CN (2) –CH3

(3) N H3 (4) All of these
Solution.
 14

4. Usually, M > I Applications of Mesomeric effect:

1. To compare Acidic Strength of Carboxylic acids

C.Q. 17. Identify correct statement/s:

(A) –OCH3 and –NHCOCH3 are activating group.
(B) –CN and –OH are meta directing group.
(C) –CN and –SO3H are meta directing group.
(D) Activating groups act as ortho and para directing
groups. C.Q. 18. The decreasing order of acidity of the following
(E) Halides are activating groups. benzoic acid derivatives is:
Choose the correct answer from the options given
below: (JEE Mains 2025)
(1) (A), (C) and (D) only
(2) (A) and (C) only
(3) (A) only
(4) (A), (B) and (E) only
Solution.

(1) P > Q > R > S (2) Q > P > S > R

(3) S > R > Q > P (4) R > S > P > Q
Solution.
 15

C.Q. 19. The three acids are given below. The order of their C.Q. 20. The ascending order of acidity of –OH group in
acidic nature is: the following compounds is:
(A) BuOH
(I) (II)
(B) O2N OH

(III) (C) MeO OH

(1) I > III > II (2) I > II > III (D) OH

(3) III > I > II (4) II > III > I
Solution.
(E)

Choose the correct answer from the options given

below: (JEE Mains 2024)
(1) (A) < (D) < (C) < (B) < (E)
(2) (C) < (A) < (D) < (B) < (E)
(3) (C) < (D) < (B) < (A) < (E)
(4) (A) < (C) < (D) < (B) < (E)
Solution.
2. To compare Acidic Strength of Phenols

C.Q. 21. Match List I with List II.

List-I List-II
(Compound) (pKa value)
A. Ethanol I. 10.0
B. Phenol II. 15.9
C. m-Nitrophenol III. 7.1
D. p-Nitrophenol IV. 8.3
Choose the correct answer from the options given
below: (JEE Mains 2024)
(1) A-I, B-II, C-III, D-IV
(2) A-IV, B-I, C-II, D-III
(3) A-III, B-IV, C-I, D-II
(4) A-II, B-I, C-IV, D-III
Solution.
 16

C.Q. 22. Statement I: The acidic strength of OP Points:

monosubstituted nitrophenol is higher than Phenol 1. Availability of Lone pair on Nitrogen, more will be
because of electron withdrawing nitro group. Basicity.
Statement II: o-nitrophenol, m-nitrophenol, p-
nitrophenol will have same acidic strength as they
one nitro group attached to the phenolic ring.
(NEET 2022)
(1) Both Statement I and Statement II are incorrect.
(2) Both Statement I and Statement II are correct.
(3) Statement I is correct and Statement II is
incorrect.
(4) Statement I is incorrect and Statement II is
correct.
Solution.

2. Localized L.P > Delocalized L.P

3. To compare Basic Strength:

3. Organic Nitrogenous Bases

Guanidine > Amidine > Amines > Imines > Amides >
Cyanides
 17

4. SIR effect
C.Q. 23. Correct order of basic strength of Pyrrole

, Pyridine and Piperidine is:

(JEE Mains 2024)

(1) Piperidine > Pyridine > Pyrrole
(2) Pyrrole > Pyridine > Piperidine
(3) Pyridine > Piperidine > Pyrrole
(4) Pyrrole > Piperidine >Pyridine
Solution.

5. SIP effect C.Q. 24. The correct increasing order of basic strength for the
following compounds is: (NEET 2017)

I II III

(1) III > I > II (2) III > II > I

(3) II > I > III (4) II > III > I
Solution.
 18

Hyperconjugation: Case 01: In Carbocations

It involves delocalization of σ electrons of C—H bond of an
alkyl group directly attached to an atom of unsaturated system
or to an atom with an unshared p orbital.

Case 02: In Free Radical

1. Hyperconjugation is a permanent effect.

2. Also Known as No Bond Resonance or Baker-Nathan

Effect.
 19

Case 03: In Alkenes OP Points:

1. CO, CN cannot show hyper due to high energy of π*
orbital.

2. Hyper conjugative structures (Involving C-H bond

breaking) =

03. Hyper conjugative structure =

Total no. of Hyperconjugating Structures:

Q. Find total number of hyper conjugative structure

(Involving C–H bond breaking).
 20

Solution. 2. Bond length

Application of Hyperconjugation: Reverse Hyperconjugation:

1. To compare stability of Carbocations, Free radicals Delocalization of π electrons to vacant orbital
and Alkenes.

C.Q. 25. How many compounds among the following

compounds show inductive, mesomeric as well as
hyperconjugation effects? (JEE Mains 2024)
 21

Solution. C.Q. 28. Considering the following alkenes:

The correct decreasing order of stability is:
CH3CH 2CH = CH 2 , (CH3 )2 C = C(CH3 ) 2 ,
But −1−ene 2,3 − Dimethyl but − 2 − ene
(I) (II)

(CH3 )2 C = CHCH3 , (CH3 )2 C = CH 2

2 − Methyl but − 2 − ene 2 − Methyl propene
(III) (IV)

(1) I > II > III > IV

(2) II > III > IV > I
C.Q. 26. Given below are two statements: (3) IV > III > II > I
Statement-I: Hyperconjugation is permanent effect. (4) III > IV > I > II
Statement-II: Hyperconjugation in ethyl cation Solution.
(CH3–CH2) involves the overlapping of Csp2 H1s
bond with empty 2p orbital of other carbon.
Choose the correct option. (JEE Mains 2021)
(1) Statement-I is false but Statement-II is true.
(2) Statement-I is true but Statement-II is false.
(3) Both Statement-I and Statement-II are false.
(4) Both Statement-I and Statement-II are true.
Solution.

C.Q. 29. Which of the following cannot exhibit

hyperconjugation?
CH 3
C.Q. 27. Assertion: 2, 3-Dimethylbut-2-ene is more stable \
• +
than but-2-ene. (1) CH3 C H 2 (2) CH
Reason: Six hyperconjugation structures can be /
written for 2, 3-dimethylbut-2-ene while but-2-ene CH 3
has twelve. +
(3) CH3CH=CH2 (4) (CH3 )3 C − C H 2
(1) Both Assertion and Reason are correct and
Reason is the correct explanation for Assertion. Solution.
(2) Both Assertion and Reason are correct but
Reason is not the correct explanation for
Assertion.
(3) Assertion is correct but Reason is incorrect.
(4) Both Assertion and Reason are incorrect.
Solution.
 22

Aromaticity: Solution.
1. Cyclic

2. Planar

C.Q. 30. Consider the following compounds/species:

3. Conjugation

4. Huckel’s Rule

The number of compounds/species which obey

Huckel's rule is………. (NEET 2023)
(1) 5 (2) 4
(3) 6 (4) 2
Solution.

Q. Comment on Aromaticity.
 23

Application of Aromaticity: 2. Dipole moment, Bond Length and Rate of

1. Stability of Intermediates Protonation

C.Q. 31. The correct stability order of the following C.Q. 32. Among the following compounds, the one which
species/molecules is: (JEE Mains 2025) shows highest dipole moment is: (JEE Mains 2023)

(1) (2)

(1) q > p > r (2) p > q > r (3) (4)

(3) r > q > p (4) q > r > p
Solution. Solution.
 24

3. Rotational Energy Barrier C.Q. 33. Among the following which is more reactive toward
AgNO3?

(1) (2)

(3) (4)

Solution.

4. Reactivity with HX and H2SO4

6. Reaction with Na, K & Al

5. Reactivity toward AgNO3 and SbCl5 7. Reaction with Fe3+

 25

Stability of Intermediates: C.Q. 34. The most stable carbocation from the following
compounds is: (JEE Mains 2025)

(1)

(2)

(3)
Stability of Carbocations:
Definition: Formed by Heterolytic bond breaking.

(4)

Solution.

C.Q. 35. Which one of the carbocations from the following

is most stable? (JEE Mains 2025)

(1)

(2)

(3)

(4)
 26

Solution. Stability of Carbanion:

Definition: Formed by Heterolytic bond breaking.

C.Q. 36. The correct order of stability of following

carbocations is: (JEE Mains 2025)

(1) C>A>B>D
(2) A>B>C>D
(3) C>B>A>D
(4) B>C>A>D
Solution.

C.Q. 37. The most stable carbocation among the following is:
(NEET 2024)
(1) C.Q. 38. Correct order of stability of carbanion is:
(JEE Mains 2024)

(2)

(3) (1) c>b>d>a

(2) a>b>c>d
(3) d>a>c>b
(4) d>c>b>a
Solution.
(4)

Solution.
 27

C.Q. 39. Arrange the following carbanions in decreasing C.Q. 40. The increasing order of stability of the following free
order of stability: radicals is: (AIIMS 2017)
• • • •
(1) ( C6 H5 )2 CH  ( C6H5 )3 C  ( CH3 )3 C  ( CH3 )2 CH
• • • •
(2) ( CH3 )2 CH  ( CH3 )3 C  ( C6H5 )2 CH  ( C6H5 )3 C
• • • •
(3) ( CH3 )2 CH  ( CH3 )3 C  ( C6H5 )2 CH  ( C6H5 )3 C
• • • •
(4) ( C6 H5 )3 C  ( C6H5 )2 CH  ( CH3 )3 C  ( CH3 )2 CH
Solution.

(1) III > II > IV > I (2) III > II > I > IV C.Q. 41. Which of the following statements is wrong?
(3) I > III > II > IV (4) III > I > II > IV (1) A tertiary free radical is more stable than a
Solution. secondary free radical.
(2) A secondary free radical is more stable than a
primary free radical.
(3) A tertiary carbocation is more stable than a
secondary carbocation.
(4) A primary carbocation is more stable than a
secondary carbocation.
Solution.
Stability of Free Radical:
Definition: Formed by Homolytic bond breaking.

C.Q. 42. Covalent bond can undergo fission in two different

ways. The correct representation involving a
heterolytic fission of CH3—Br is:

(1)

(2)

(3)

(4)
Solution.
 28

Heat of Hydrogenation: C.Q. 43. The order of heat of hydrogenation in following

Definition: The amount of energy released during compound is:
hydrogenation reaction.

(1) I < II < IV < III (2) III < IV < II < I
(3) II < III < I < IV (4) II < IV < 1 < III
Solution.

Compare Heat of Hydrogenation:

C.Q. 44. Assertion: Heat of hydrogenation of CH2 = CH2

is greater than CH3CH = CH2.
Reason: -CH3 give additional effect to double bond.
(1) Both Assertion and Reason are correct and
Reason is the correct explanation for Assertion.
(2) Both Assertion and Reason are correct but
Reason is not the correct explanation for
Assertion.
(3) Assertion is correct but Reason is incorrect.
(4) Both Assertion and Reason are incorrect.
Solution.
 29

Heat of Combustion: Resonance Energy:

Definition: The amount of energy released during combustion Definition: The potential energy difference between
reaction. resonance hybrid and most stable resonating structure.

Compare Heat of Combustion:

1. R.E is always negative.

2. R.E can be calculated by HOH data.

Compare Resonance Energy:

C.Q. 45.

The correct order of heats of combustion of above

compounds is:
(1) I > II > III (2) II > I > III
(3) III > II > I (4) III > I > II
Solution.
 30

C.Q. 46. Assertion (A): Energy of resonance hybrid is Acidic Strength in different families:
equal to the average of energies of all canonical
forms.
Reason (R): Resonance hybrid cannot be presented
by a single structure. (NCERT Exemplar)
(1) Both A and R are correct and R is the correct
explanation of A.
(2) Both A and R are correct but R is not the correct
explanation of A.
(3) Both A and R are not correct.
(4) A is not correct but R is correct.
Solution.

C.Q. 47. Which of the following has highest resonance

energy?

(1) (2)

C.Q. 48. Which one is the correct order of acidity?

(3) (4) (NEET 2017)
(1) CH ≡ CH > CH3 – C ≡ CH > CH2 = CH2 > CH3
– CH3
(2) CH ≡ CH > CH2 = CH2 > CH3 – C ≡ CH > CH3
– CH3
(3) CH3 – CH3 > CH2 = CH2 > CH3 – C ≡ CH > CH
≡ CH
(4) CH2 = CH2 > CH3 – C ≡ CH > CH3 – CH3 > CH
≡ CH
Solution.
 31

C.Q. 49. Which of the following orders of acid strength is 2. NaOH Test
correct? (AIPMT 2003)
(1) RCOOH > ROH > HOH > HC ≡ CH
(2) RCOOH > HOH > ROH > HC ≡ CH
(3) RCOOH > HOH > HC ≡ CH > ROH
(4) RCOOH > HC ≡ CH > HOH > ROH
Solution.

Application of Acidic Strength in different families:

How to check the feasibility of Reaction on
microseconds in Pankaj sir’s style?

C.Q. 50. Which of the following are soluble in aq. NaOH

solution?

(1) (2)

1. Na, NaH & NaNH2 Test (3) (4)

Solution.
 32

3. NaHCO3 Test C.Q. 52. Compound which is soluble in NaOH & NaHCO3
both?

(1)

(2)

(3) (4)

Solution.

C.Q. 51. The compounds that produce CO2 with aqueous

NaHCO3 solution are:

Tautomerism:

Choose the correct answer from the options given

below: (JEE Mains 2025)
(1) A, B and E Only
(2) A and C Only
(3) A, C and D Only
(4) A and B Only
Solution.
 33

Enol Content: C.Q. 53. Highest enol content will be shown by:
(JEE Mains 2024)

(1) (2)

(3) (4)

Solution.
Enol Content Order:

C.Q. 54. Which among the following compounds will give

maximum enol content:
O O
(1) || ||
C6 H5 − C− CH 2 − C− CH3
O O
(2) || ||
CH3 − C− CH 2 − C− CH3
O
(3) ||
CH3 − C− CH 2 − CH 2 − CH3
O
(4) ||
CH3 − C− CH 2 − COOC2 H5
Solution.
 34

Electrophile: Solution.

1. Electron loving species

2. Having or not having vacant orbital

C.Q. 56. Which of the following species is not

electrophilic in nature? (AIPMT 2010)

(1) Cl (2) BH3
 
(3) H3 O (4) NO2
Solution.

Nucleophile:
1. Electron Rich and Precise Species
2. Having or not having lone pair

C.Q. 55. The correct statement regarding electrophiles is:

(NEET 2017)

(1) Electrophile can be either neutral or positively

charged species and can form a bond by
accepting a pair of electrons from a nucleophile
(2) Electrophile is a negatively charged species and
can form a bond by accepting a pair of electrons
from a nucleophile.
(3) Electrophile is a negatively charged species and
can form a bond by accepting a pair of electrons
from another electrophile.
(4) Electrophiles are generally neutral species and
can form a bond by accepting a pair of electrons
from a nucleophile.
 35

C.Q. 57. Which of the following statements is not correct Types of Reaction:
for a nucleophile? (NEET 2015)
(1) Nucleophiles are not electron seeking.
(2) Nucleophile is a Lewis acid.
(3) Ammonia is a nucleophile.
(4) Nucleophiles attack low electron density sites.
Solution.

C.Q. 58. Nucleophile is a species that should have

(1) A pair of electrons to donate

(2) Positive charge
(3) Negative charge
(4) Both (1) & (3)
Solution.

C.Q. 59. Identify the reagents shown in bold in the

following equations as nucleophiles or electrophiles:
A. CH3COOH + HO— → CH3COO— + H2O
B. CH3COCH3 + CN — →(CH3)2C(CN)(OH)
Q. Match the following:
C. C6H6 + CH3CO+ → C6H5COCH3
(a) Substitution reaction (i) A : B→ A+ : B–
Solution.
(b) Addition reaction (ii) A : A → Å + Å
KOH
(c) Elimination reaction (iii) CH3Cl→ CH3OH
(d) Homolytic fission (iv) BF3
(e) Heterolytic fission (v) H2C=CH2 + HBr →
CH3CH2Br
(f) Electrophile (vi)
H2 SO4
CH3CH2OH→ H2C=CH2
(g) Nucleophile (vii) NH3
 36

Solution. Solution.

C.Q. 61. R − X + NaOH → ROH + NaX

The above reaction is classified as
C.Q. 60. Classify the following reactions in one of the (1) Nucleophilic substitution
reaction type studied in this unit. (2) Electrophilic substitution
(3) Reduction
(1) CH3CH2Br + HS—→ CH3CH2SH + Br—
(4) Oxidation
(2) (CH3)2 C = CH2 + HCl → (CH3)2 ClCCH3 Solution.
(3) CH3CH2Br + HO— →CH2 = CH2 + H2O + Br
(4) (CH3) 3CCH2OH + HBr →
(CH3)2CBrCH2CH2CH3 + H2O

“किसी भी िार्य िरने िे किए तुरन्त उठो, जागो और तब ति नही रुिना जब ति िक्ष्य हाकसि न हो जाए”
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Practice Problems
Organic Chemistry Some Basic principles and Techniques
(GOC)

Q1 (B)

(C)
(A) +I effect of –CH3 group
(B) –I effect of –CH3 group
(D)
(C) Hyperconjugation effect of –CH3 group
(D) Steric inhibition of protonation by –CH3
group

Q2 Arrange the following in the correct decreasing Q5 Given below are two statements: one is labelled
order of acidic strength. as Assertion A and the other is labelled as
(I) 2, 4, 6-Trinitrophenol Reason R:
(II) 2, 4-Dinitrophenol Assertion A: Tertiary butyl carbanion is less
(III) o-Nitrophenol stable than methyl carbanion.
(IV) p-Nitrophenol Reason R: +I effect of the three methyl groups in
(A) I > II > III = IV tertiary butyl carbanion tends to make it less
(B) IV > III > II > I stable than methyl carbanion.
(C) I > II > IV > III In the light of the above statements, choose the
(D) III > II > I > IV correct answer from the options given below:
(A) A is true but R is false.
Q3 Which of following has lowest pKa value?
(B) A is false but R is true.
(A) Cl − CH2 − CO2 H
(C) Both A and R are true and R is the correct
(B)
explanation of A.
(D) Both A and R are true but R is NOT the
(C) Cl3 C − CO2 H correct explanation of A.
(D) CH3 − CO2 H
Q6 The reaction intermediate produced by
Q4 Which of the following hydrocarbon is most homolytic cleavage of bond is called:
acidic? (A) carbocations. (B) carbanions.
(A) (C) free radicals. (D) carbenes.

Q7 Decreasing order of stability of given

carbocations is as:

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Q11 In which of the following pairs of carbocations,

the first carbocation is more stable than the
second?
+

(i) CH2 = CH − CH2 and

+

CH2 = CH − CH2 − CH2

⊕ + +

II. CH3 − CH2 (ii) CH3 − NH − CH2 and CH2 − OH

⊕ +

III. C6 H5 − CH2 (iii) CH3 − O − CH2 − CH2 and

⊕ +

IV. CH3 CH3 − O − CH2

+

(iv) CH3 − CH − CH2 CH2 CH3 and

(A) III > II > IV > I +

(B) I > III > IV > II CH3 CH2 − CH − CH2 CH3

(C) I > III > II > IV (A) (i), (ii) and (iii)
(D) III > II > I > IV (B) (i), (ii) and (iv)
(C) (ii) and (iii)
Q8 Which one of the following carbanions is least (D) (iii) and (iv)
stable ?
(A) CH3 CH− (B) HC ≡ C
− Q12 Given below are two statements: one is labelled
2

(C) (C6 H5 )3 C− (D) (CH3 )3 C− as Assertion A and the other is labelled as

Reason R:
Q9 Which of the following is maximum stable Assertion (A): Tertiary carbocations are
carbocation? generally formed more easily than primary
(A) carbocations.
Reason (R): Hyperconjugations as well as
inductive effect due to additional alkyl groups

(B) stabilize tertiary carbocations.

In the light of the above statements, choose the
correct answer from the options given below:
(A) A is true but R is false.
(C) (B) A is false but R is true.
(C) Both A and R are true and R is the correct
explanation of A.
(D) (D) Both A and R are true but R is NOT the
correct explanation of A.

Q13 Which of the following is not an electrophile?

Q10 Which of the following is the most stable (A) CN– (B) BF3
carbanion? (C) NO2+ (D) AlCl3
(A) ⊝

CH2 CH2 − NO2 Q14 The decreasing order of stability of following

(B) ⊝
cations is
CH2 CH2 − CN

(C) ⊝

CH2 CH2 − Br

(D) ⊝

CH2 CH3

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Q17 Which of the following species can show

conjugation?
(A)

(A) P > Q > R > S

(B) CH2 = CH − Cl
(B) Q > S > R > P
(C)
(C) Q > P > S > R

(D) Q > P > R > S

Q15 Which of the following have all resonating (D) All of these
structure identical?
Q18 Which of the following compounds will show the
(A)
maximum 'enol' content?
(A) CH3 COCH3
(B) CH3 COCH2 COCH3
(C) CH3 COCH2 COOC2 H5
(D) CH3 COCH2 CONH2
(B)
Q19 How many π electrons are there in the following
species?
(C)

(D)

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

Q20 Among the following the aromatic compound is:

(A)

Q16

(B)

The most stable canonical structure among these

is: (C)
(A) III
(B) II
(C) I
(D) all are equally stable (D)

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(C) 5 (D) 4

Q23 The correct order for the stability of given

alkenes is:
(I)

Q21 Which of the following compound is

nonaromatic?
(A) (II)

(III) CH3 − CH = CH2

(B) (A) III > II > I

(B) II > III > I
(C) I > II > III
(D) I > III > II

(C) Q24 Which of the following can not show

hyperconjugation?
(A)

(D)
(B)

Q22 Consider the following compounds/species:

(C)

(D)

Q25 Which of the following order represent acidic

strength of (I) benzoic acid, (II) 4-nitrobenzoic
acid, (III) 3,4-dinitrobenzoic acid and (IV) 4-
methoxybenzoic acid?
(A) I < II < III < IV
(B) IV < I < II < III
The number of compounds/species which obey (C) II < III < I < IV
Huckel's rule is ______. (D) IV < II < III < I
(A) 6 (B) 2

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Q26 Match List-I with List-II.

(C) CH3 CH = CH2

(D) +

(CH3 ) C− C H2
3

Q29 Inductive effect involves;

(A) displacement of σ− electrons.
(B) delocalization of σ− electrons.
(C) delocalization of π−electrons.
(D) displacement of π−electrons.

Q30 Which of the following is most stable?

Choose the correct answer from the options (A)
given below:
(A) A-I, B-III, C-II, D-IV
(B) A-IV, B-III, C-II, D-I
(B)
(C) A-II, B-III, C-IV, D-I
(D) A-II, B-I, C-III, D-IV

Q27 Compare heat of hydrogenation of the following (C)

(i)

(D)

(ii)

Q31 At resonating position, –NO2 imparts:

(A) +R, +I
(B) –R, –I
(iii) (C) +R, –I
(D) –R, +I

Q32 The bond order of individual carbon-carbon

bonds in benzene is:
(A) one.
(A) i > ii > iii
(B) one and two alternately.
(B) iii > ii > i
(C) between one and two
(C) ii > i > iii
(D) two
(D) ii > iii > i
Q33 Which of the following is the incorrect order of -I
Q28 Which of the following cannot exhibit
effect?
hyperconjugation?
(A) −NO2 > −CN > −COOH
(A) CH3 CH
˙
2
(B) −F > Cl > −Br > −I
(B)
(C)

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⊕ ⊕ ⊕
(C) IV > III > II > I
− N H3 > − N H2 Me > − N HMe 2
(D) IV > II > I > III
(D) −C ≡ CH > −Ph > −CH = CH2

Q37 The inductive effect of the groups:

Q34 Which of the following has longest C–O bond
length? are respectively:
(A) (A) –I, +I, +I, –I
(B) –I, –I, –I, +I
(C) –I, +I, –I, –I
(D) +I, –I, –I, –I
(B)
Q38 What is correct stability order of following given
carbanions:

(C)

(D)

(A) A > B > C

(B) C > B > A
Q35 Which of the following alkyl group has the
(C) B > A > C
maximum + I effect?
(D) A > C > B
(A) (CH3 )2 CH−
(B) (CH3 )3 C− Q39 Resonance involves:
(C) CH3 CH2 − (A) Delocalization of π -electrons along a
(D) CH3 − conjugated system.
(B) Delocalization of lone pairs along a
Q36 Arrange in the decreasing order of stability;
conjugated system.
(C) Delocalization of negative charge along a
conjugated system.
(D) All are correct

Q40 Which free radical is the most stable?

(A) CH3 ˙
− CH2

(B) CH3 ˙
− CH2 − CH2

(C) CH3 ˙
− CH − CH3

(D)

Q41
(A) I > IV > III > II
(B) II > I > III > IV and are:

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(A) resonating structures

(B) tautomers
(C) geometrical isomers
(D) optical isomers

Q42

The correct order of stability of given

carbocations is:
(A) A > C > B > D
(B) D > B > C > A
(C) C > A > D > B (A) Q > R > S > P
(D) D > B > A > C (B) R > Q > P > S
(C) S > P > R > Q
Q43 Which of the following is the most stable free (D) P > Q > R > S
radical?
(A) CH3 ĊH2 Q46 Identify the correct order of reactivity of
(B) CH3 ĊHCH3 electron density on benzene ring in the given
(C) CH3 ĊHC6 H5 compounds:

(D) C6 H5 CH2 CH
˙
2

Q44 Most stable free radical among the following is:

(A)

(A) A > B > C > D

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

Q47 The shape of carbocation is :

(A) tetrahedral
(C)
(B) trigonal planar
(C) trigonal pyramidal
(D) diagonal

Q48 Among the following compounds, the strongest

(D) acid is;
(A) HC ≡ CH (B) C6H6
(C) C2H6 (D) CH3OH

Q49 The most stable carbanion among the following

Q45
is

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(A)

(B)

(C)

(D)

Q50 Arrange following in order of Ka value:

A. C6 H5 OH

B. CH3 OH
C. CH3 COOH
D. CH3 SO3 H
(A) A > C > D > B
(B) D > C > A > B
(C) A> C > B > D
(D) B > A > C > D

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Answer Key
Q1 (D) Q26 (A)

Q2 (C) Q27 (B)

Q3 (C) Q28 (D)

Q4 (A) Q29 (A)

Q5 (C) Q30 (A)

Q6 (C) Q31 (B)

Q7 (C) Q32 (C)

Q8 (D) Q33 (C)

Q9 (C) Q34 (B)

Q10 (A) Q35 (B)

Q11 (B) Q36 (B)

Q12 (C) Q37 (A)

Q13 (A) Q38 (A)

Q14 (D) Q39 (D)

Q15 (B) Q40 (D)

Q16 (A) Q41 (A)

Q17 (D) Q42 (A)

Q18 (B) Q43 (C)

Q19 (C) Q44 (C)

Q20 (C) Q45 (A)

Q21 (D) Q46 (C)

Q22 (D) Q47 (B)

Q23 (C) Q48 (D)

Q24 (D) Q49 (D)

Q25 (B) Q50 (B)

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