General Organic Chemistry

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Exercise - I
Attacking Reagent 8. The correct order of stability of given
1. Which of the following species is an carbanions will be :-
electrophile CH3–CH2 CH2=CH HCC
(1) RNH2 (2) SO3 (3) NO Θ
3 (4) ROH (I) (II) (III)

2. Which of the following acts as a nucleophile? (1) I > II > III (2) III > II > I
 Θ  (3) I > III > II (4) II > I > III
(1) NO2 (2) :CCl2 (3) NH2 (4) C H3 9. Which is most basic among the following :-
(1) CH3NH2 (2) CH3CH2NH2
Reaction Intermediates (3) NH3 (4) (CH3)2CHNH2
3. Which of the following contains three pair of 10. Which of the following has maximum pKa :-
electrons : (1) CH2FCOOH (2) CH2ClCOOH
(3) CH3COOH (4) HCOOH
(1) Carbanion
11. Which of the following show + I-effect :-
(2) Carbocation
(1) –OH (2) –OCH3 (3) –CH3 (4) –Cl
(3) Carbon free radical
12. The strongest acid amongst the following
(4) None compounds is ?
4. Carbanion is a :- (1) CH3CH2CH(Cl)CO2H
(1) Base (2) Nucleophile (2) ClCH2CH2CH2COOH
(3) Both the above (4) None (3) CH3COOH
(4) HCOOH
I-Effect 13. Which of the following acids is stronger than
Θ acetic acid :-
5. CH3 is less stable than :-
(1) Propanoic acid (2) HCOOH
Θ
(1) CH3— CH2
Θ
(2) CH3— CH —CH3 (3) Butyric acid (4) (CH3)2CHCOOH
Θ
14. Which of the following acids have the lowest
Θ
(3) CH2 —NO2 (4) CH3— CH —C2H5 pKa value :-
Cl
6. Decreasing order of –I effect of the triad
 (1) CH3–CH–COOH (2) Cl–CH2–CH2–COOH
[–NO2, – N H3 , –CN] is :-

(3) CCl3COOH (4) CHCl2COOH
(1) – NH3 > –NO2 > –CN
 R- or M-Effect
(2) – NH3 > –CN > NO2
15. Most stable carbocation is :-

 
(3) –CN > –NO2 > – NH3 CH2 CH2

(4) –NO2 > –CN > – N H3
(1) (2)

7. CH3 − CH − CH 3 is less stable than
Cl NO2
CH3  
  CH2
(1) CH3–C (2) CH3 − CH2 CH2

CH3 (3) (4)


(3) CH 3 (4) None of these OCH3
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16. Most acidic compound is :- 22. The most stable carbanion among thehfollowing
alnaaya
aar

(1) OH
is
CH2–CH2 CH2
(2) CO2H (1) (2)

(3) H3C CO2H CH2 CH2

(4) O2N CO2H (3) (4)

17. Which resonating structure of vinyl chloride OCH3 NO2

is least stable :- 23. The oxygen atom in phenol –
(1) CH2=CH– Cl: (1) Exhibits only inductive effect
Θ  (2) Exhibits only resonance effect
(2) CH2 –CH= Cl (3) Has more dominating resonance effect
Θ 
than inductive effect
(3) CH2 – CH –Cl
(4) Has more dominating inductive effect
(4) All have equal stability
than resonance effect
18. The stabilization due to resonance is 24. Mesomeric effect is due to :-
maximum in
(1) Delocalization of  es
(1) (2) (2) Delocalization of  es
(3) Migration of H – atom
(3) (4) (4) Migration of proton
25. Which of the following is least basic :–
19. In which of the following compounds carbon– NH2 NH2
chlorine bond distance is minimum :-
(1) CH3—Cl (2) C6H5—CH2—Cl (1) (2)
(3) CH2=CH—Cl (4) CH2=CH—CH2—Cl NO2 OCH3
20. Consider the following carbocations
NH2 NH2

(a) CH3O CH2
(3) (4)

(b) CH2 Cl CH3
 26. Among the following the aromatic is
(c) CH3 CH2
(1) (2)

(d) CH3 − CH2 

The relative stabilities of these carbocations (3) (4)

are such that :-
27. Which is aromatic among the following
(1) d < b < c < a (2) b < d < c < a

(3) d < b < a < c (4) b < d < a < c (1) (2)
21. Among the following, the strongest base is :-
(1) C6H5NH2 (2) p–NO2–C6H4NH2 (3) (4) All the above
N
(3) m–NO2–C6H4NH2 (4) C6H5CH2NH2
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28. Select the correct option for stability of 35. Among the following the strongest acid is :-aaar
following carbanions : (1) CH3COOH
CH3 (2) C6H5COOH
Θ Θ
CH3 ; C6 H5 CH2 ; CH3–C (3) m–CH3OC6H4COOH
(I) (II)
(4) p–CH3OC6H4COOH
CH3
36. Which one of the following resonating
(III)
structures of 1–methoxy–1,3–butadiene is
(1) I > II > III (2) II > I > III least stable :–
(3) III > II > I (4) II > III > I Θ 
(1) CH2 –CH=CH–CH= O –CH3
29. The non aromatic compound among the Θ 

following is :- (2) CH2=CH– CH–CH= O –CH3

Θ 
(1) (2) (3) CH2– CH–CH=CH–O–CH3
S
(4) CH2=CH–CH=CH–O–CH3
(3) (4) 37. Four structures are given in options (a) to (d).
N
Examine them and select the aromatic
30. Which one of the following compounds is most strucutures.
acidic :-
(a) + (b)
OH OH
(1) (2)
NO2 CH3 (c) (d)
OH
(1) a and d (2) b and c
(3) (4) ClCH2CH2OH
(3) a and b (4) a and c
31. Which of the following is most acidic :- 38. Phenol is less acidic than
(1) Ethanol (2) o-Nitrophenol
(1) phenol (2) benzyl alcohol
(3) o-Methylphenol (4) o-Methoxyphenol
(3) m-chloro phenol (4) cyclohexanol
39. Arrange the following acid in decreasing
32. Which of the following is the strongest base :-
order of their acidic strength.
(1) NH2 (2) NH–CH3 COOH COOH

(3) NH2 (4) CH2–NH2 (i) (ii)

CH3 OCH3 Cl
33. Which is Aromatic compound :- OH COOH

(iii) (iv)
(1) (2)
NO2
N (1) iii > ii > iv > i (2) ii > iv > i > iii
(3) (4) 2 and 3 both (3) i > iii > ii > iv (4) iv > ii > iii > i
N
34. Which of the following is the most acidic Hyperconjugation
compound :- 40. Which of the following compounds exhibits
(1) CH2 = CH2 (2) HC  CH hyperconjugation :
(1) Phenol (2) Ethyne
(3) (4)
(3) Ethanol (4) Propene
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41. Which of the following is least stable :– 44. Which of the following will lead to maximum aaar
 
(1) CH3 − CH− CH3 (2) CH3 − CH2 − CH2 enolisation :–
CH3 O
  (1) CH3–C–CH3
(3) CH3–C–CH3 (4) CH3–C–CH–C6H5
CH3 CH3 (2) CH3–C–CH2–C–H
O O
42. Which of the following is most stable alkene :-
H H (3) CH3–C–CH–C– CH3
(1) C=C
O Br O
H H
CH3 H (4) All have equal
(2) C=C H2N–C–NH2
H H 45. Urea molecule exhibits which
O
H5C2 H
(3) C=C type of isomerism:-
H H
(1) Chain (2) Position
CH3 (3) Geometrical (4) Tautomerism
CH H
(4) CH3 C=C 46. Tautomerism is not observed in :–
H H (1) CH3–C–CH3 (2) Ph–CH=CH–OH
O
Tautomerism CH3
43. Tautomerism is due to :- (3) CH3–NO2 (4) CH3–C–CHO
(1) Delocalization of sigma electrons CH3
(2) Delocalization of pi electrons
(3) Migration of active–H–atom
(4) None is correct

EXERCISE-I (Conceptual Questions) ANSWER KEY

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

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Exercise - II (Previous Year Questions)
AIPMT 2006 AIPMT 2010
1. Which of the following is more basic than 5. Which one of the following compounds has
aniline the most acidic nature ?
OH
(1) Diphenyl amine (2) Triphenyl amine
CH CH2OH
(3) p-nitro aniline (4) Benzyl amine (1) (2)

(3) OH (4) OH
AIPMT 2007
2. Which of the following presents the correct 6. Given are cyclohexanol (I), acetic acid (II),
order of the acidity in the given compounds : 2, 4, 6–trinitrophenol (III) and phenol (IV). In
(1) FCH2COOH > CH3COOH > BrCH2COOH these the order of decreasing acidic character
> ClCH2COOH will be :-
(1) III > IV > II > I (2) III > II > IV > I
(2) BrCH2COOH > ClCH2COOH > FCH2COOH
(3) II > III > I > IV (4) II > III > IV > I
> CH3COOH
(3) FCH2COOH > ClCH2COOH > BrCH2COOH AIPMT Mains-2010
> CH3COOH 7. Among the following four compounds :-
(4) CH3COOH > BrCH2COOH > ClCH2COOH (a) Phenol (b) Methyl phenol
> FCH2COOH (c) Metanitrophenol (d) Paranitrophenol,
The acidity order is :
(1) c > d > a > b (2) c > d > c > b
AIPMT 2008
(3) b > a > c > d (4) d > c > a > b
3. The stability of carbanions in the following:- 8. Which of the following species is not
Θ electrophilic in nature :-
(a) RC  C (b) 
(1) BH3 (2) H 3O
Θ Θ
(c) R2C = CH (d) R 3C − CH2  
(3) NO2 (4) Cl
is in the order of:-
(1) (d) > (b) > (c) > (a) AIPMT Mains-2011
(2) (a) > (c) > (b) > (d) 9. Which of the following compounds is most
(3) (a) > (b) > (c) > (d) basic ?
(4) (b) > (c) > (d) > (a) (1) NH2 (2) O2N NH2
4. Basic strength of:-
•• ••
Θ (3) CH2NH2 (4) N–COCH3
(a) H3C − CH2
Θ
H
(b) H2C = CH and
AIPMT Pre.-2012
Θ
(c) HC  C 10. The correct order of decreasing acid strength
is in the order of:- of trichloroacetic acid (A), trifluoroacetic acid
(B), acetic acid (C) and formic acid (D) is:
(1) (a) > (c )> (b) (2) (a) > (b) > (c)
(1) A > B > C > D (2) A > C > B > D
(3) (b )> (a) > (c) (4) (c) > (b) > (a) (3) B > A > D > C (4) B > D > C > A
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NEET-UG 2013 15. Given :- aaar

11. The radical, CH2• is aromatic because H3C CH3 H3C CH2 H2C CH2

it has:-
(1) 6p–orbitals and 7 unpaired electrons CH3 CH3 CH2
(2) 6p–orbitals and 6 unpaired electrons (I) (II) (III)
(3) 7p–orbitals and 6 unpaired electrons The enthalpy of the hydrogenation of these
(4) 7p–orbitals and 7 unpaired electrons
compounds will be in the order as :-
12. The order of stability of the following
(1) III > II > I (2) II > III > I
tautomeric compounds is :-
(3) II > I > III (4) I > II > III
OH O
CH2=C–CH2–C–CH3 16. Which of the given compounds can exhibit
(I) tautomerism ?
O O CH3 CH3
CH3
CH3–C–CH2–C–CH3 CH3
CH3
(II) CH3
OH O O O O

CH3–C=CH–C–CH3 (I) (II) (III)

(III) (1) I and III (2) II and III
(1) II > III > I (2) I > II > III (3) I, II and III (4) I and II
(3) III > II > I (4) II > I > III 17. Which of the following is the most correct
electron displacement for a nucleophilic
AIPMT 2015 reaction to take place?
13. In which of the following compounds, C–Cl
bond ionisation shall give most stable H H2
(1) H3C C = C – C – Cl
carbonium ion? H
H
H3 C CH–Cl H H2
(2) H3C C = C – C – Cl
(1) C–Cl (2) H
H3C
CH3
H H2
H (3) H3C C = C – C – Cl
H3C H H
(3) C–Cl (4) C–Cl
O2NH2C H H H2
H3 C
(4) H3C C = C – C – Cl
14. Consider the following compounds H
CH3 Ph Re-AIPMT 2015
• •
CH3–C–CH– Ph–C–Ph
•
18. Which of the following statements is not
CH3
CH3 correct for a nucleophile ?
(I) (II) (III) (1) Nucleophiles attack low e– density sites
Hyperconjugation occurs In :- (2) Nucleophiles are not electron seeking
(1) II only (2) III only (3) Nucleophile is a Lewis acid
(3) I and III (4) I only (4) Ammonia is a nucleophile
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19. Correct order of Kb is (3) Arylamines are generally more basic than
aaar
CH2NH2 NH2 alkylamines because of aryl group.
(4) Arylamines are generally more basic than
(i) (ii)
alkylamines, because the nitrongen atom
(iii) CH3CH2–NH2 (iv) H3C–C–NH2 in arylamines is sp-hybridized.
O NEET-II 2016
22. In pyrrole
(1) iv > iii > ii > i (2) iii > i > ii > iv
4 3
(3) i > ii > iii > iv (4) ii > iii > iv > i
5 2
••
N1
NEET-I 2016
20. The correct statement regarding a carbonyl H
compound with a hydrogen atom on its The electron density is maximum on :-
alpha carbon, is :- (1) 2 and 4 (2) 2 and 5
(1) A carbonyl compound with a hydrogen (3) 2 and 3 (4) 3 and 4
atom on its alpha-carbon never 23. Which among the given molecules can exhibit
equilibrates with its corresponding enol. tautomerism ?
(2) A carbonyl compound with a hydrogen O O
atom on its alpha-carbon rapidly O O Ph
equilibrates with its corresponding enol
Ph
and this process is known as aldehyde-
I II III
ketone equilibration.
(3) A carbonyl compound with a hydrogen (1) Both I and II (2) Both II and III
atom on its alpha-carbon rapidly (3) III only (4) Both I and III
equilibrates with its corresponding enol 24. The correct order of strengths of the
and this process is known as carboxylic acids
carbonylation. COOH COOH COOH
(4) A carbonyl compound with a hydrogen O
O
atom on its alpha-carbon rapidly
I II III
equilibrates with its corresponding enol
and this process is known as keto-enol is
tautomerism. (1) III > II > I (2) II > I > III
21. The correct statement regarding the basicity (3) I > II > III (4) II > III > I
of arylamines is :- NEET(UG) 2017
(1) Arylamines are generally less basic than 25. Which one is the correct order of acidity ?
alkylamines because the nitrogen lone- (1) CH  CH > CH3 – C  CH > CH2 = CH2
pair electrons are delocalized by > CH3 – CH3
interaction with the aromatic ring  (2) CH  CH > CH2 = CH2 > CH3 – C  CH
electron system.
> CH3 – CH3
(2) Arylamines are generally more basic than
(3) CH3 – CH3 > CH2 = CH2 > CH3 – C  CH
alkylamines because the nitrogen lone-
> CH  CH
pair electrons are not delocalized by
(4) CH2 = CH2 > CH3 – CH = CH2 > CH3 – C  CH
interaction with the aromatic ring 
electron system. > CH  CH
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26. Which one is the most acidic compound ? NEET(UG) 2018 aaar

OH OH 29. Which of the following is correct with respect

to –I effect of the substituents ? (R = alkyl)
(1) (2) (1) – NH2 < – OR < – F
(2) –NR2 < – OR < – F
NO2
(3) – NH2 > – OR > – F
OH (4) – NR2 > – OR > – F
OH
O2 N NO2
(3) (4)
NEET(UG) 2019
CH3 30. The correct order of the basic strength of
NO2
methyl substituted amines in aqueous solution
27. The correct increasing order of basic strength is :-
for the following compounds is : (1) (CH3)2NH > CH3NH2 > (CH3)3N
NH2 NH2 NH2 (2) (CH3)3N>CH3NH2 > (CH3)2NH
(3) (CH3)3N>(CH3)2NH>CH3NH2
(I) (II) (III)
(4) CH3NH2>(CH3)2NH > (CH3)3N
NO2 CH3 31. The compound that is most difficult to
protonate is:-
(1) III < I < II
O O
(2) III < II < I (1) H H (2) H C H
3

(3) II < I < III O O

(3) H C CH3 (4) Ph H
3
(4) II < III < I
28. The correct statement regarding electrophile
NEET(UG) 2019 (ODISHA)
is:-
32. The most stable carbocation, among the
(1) Electrophile is a negatively charged following is :-
species and can form a bond by accepting 
(1) (CH3 )3 C − CH− CH3
a pair of electrons from another 
(2) CH3 − CH2 − CH− CH2 − CH3
electrophile


(2) Electrophiles are generally neutral species (3) CH3 − CH− CH2 − CH2 − CH3

and can form a bond by accepting a pair (4) CH3 − CH2 − CH2
of electrons from a nucleophile
(3) Electrophile can be either neutral or NEET(UG) 2020
positively charged species and can form a 33. A tertiary butyl carbocation is more stable
than a secondary butyl carbocation because of
bond by accepting a pair of electrons
which of the following ?
from a nucleophile
(1) Hyperconjugation
(4) Electrophile is a negatively charged (2) –I effect of –CH3 groups
species and can form a bond by accepting (3) +R effect of –CH3 groups
a pair of electrons from a nucleophile (4) –R effect of –CH3 groups

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NEET(UG) 2020 (COVID-19) aaar
34. Which of the following substituted phenols is
the strongest acid?
OH OH

(1) (2)

NO2 OCH3
OH OH

(3) (4)

C 2 H5 CH3

EXERCISE-II (Previous Year Questions) ANSWER KEY

Question 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Answer 4 3 3 2 3 2 4 2 3 3 2 3 2 2 1
Question 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Answer 3 2 3 2 4 1 2 3 4 1 3 3 3 1 1
Question 31 32 33 34
Answer 4 3 1 1

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Exercise – III (Analytical Questions)
1. Which hydrogen in the following hydrogen is 5. Select the correct option for stability of
most acidic :- following resonance structures :-
O
O CH2 , O CH2 , O CH2
CH3–CH2–CH2–C–H
4 3 2 1 x y z

(1) C1–H (2) C2–H (1) x > y > z (2) z > y > x
(3) y > x > z (4) y > z > x
(3) C3–H (4) C4–H
6. (a) CH2=CH—CH=CH2
2. Which of the following has the most acidic
(b) CH3—CH=CH2
proton: (c) CH3—CH3
O C—C single bond distance would be :-
(1) CH3 C CH3 (1) a < b < c (2) a > b < c
O (3) a < b > c (4) a < b > c
7. Which is wrong electromeric effect :
(2) CH3 C H 
(1) C=O ⎯→ C–O
(3) CH3 C CH2 C CH3
 Θ
O O (2) CH3–CH=CH2 ⎯→ CH3 − CH− CH2
Θ 
O
(3) CCl3–CH=O ⎯→ CCl3 − C H = O
C CH3  Θ
(4) CHCH ⎯→ CH = CH
(4) CH3 C CH C CH3 8. Tautomerism is exhibited by :-
O O O
CH3 CH3 O
3. Which is not aromatic compound :- (1) CH (2) CH3–CH2–N
3 CH3 O
••
O
•• O
(1) (2) O CH=O

 O
(3) (4)

(3) (4) O
9. Identify the compound that exhibits
tautomerism :-
4. The correct order of decreasing basic (1) 2-Pentanone (2) Formaldehyde
strength is (3) 2-Butene (4) Lactic acid
NH2 10. Arrange the following in correct order of
acidic strength :
I II III IV (I) CH3—NO2 (II) NO2—CH2—NO2
N N N
(III) CH3—CH2—NO2 (IV) NO2–CH–NO2
H H NO2
(1) I > II > III > IV (2) II > III > I > IV (1) IV > II > I > III (2) IV > II > III > I
(3) II > IV > I > III (4) II > III > IV > I (3) III > I > II > IV (4) III > I > IV > II
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11. The correct order of stability of following (1) Both statement I and statementalnII
aayare
aaar

carbon free radical is :- incorrect.

• (2) Statement I is correct but statement II is
(CH3 )3 C
incorrect.
(1)
(3) Statement I is incorrect but statement II is
• •
CH3CH2CH2 CH 3 correct.
(3) (4) (4) Both statements I and statements II are
correct.
(1) 1 > 2 > 3 > 4 (2) 4 > 3 > 2 > 1
14. Given below are two statements; one is
(3) 2 > 3 > 1 > 4 (4) 2 > 1 > 3 > 4
labelled as Assertion (A) and the other is
12. Given below are two statements:
labelled as Reason(R) .
Statement-I : Polarisation of  bond caused
Assertion : Hybridisation influence the bond
by polarisation of alternate  bond is reffered
length and bond enthalpy (strength) in
to as inductive effect. organic compounds.
Statement-II : Inductive effect decreases Reason : The change in hybridisation affect
rapidly as the number of intervening bonds the electronegativity of that atom. This
increases and vanishingly small after three relative electronegativity is reflected in
bonds. several physical and chemical properties.
In the light of the above statements, choose In the light of the above statements, choose
the most appropriate answer from the the most appropriate answer from the
options given below: options given below:
(1) Both statement I and statement II are (1) Both (A) and (R) are correct and (R) is the
incorrect. correct explanation of (A).
(2) Statement I is correct but statement II is (2) Both (A) and (R) are correct but (R) is not
incorrect. the correct explanation of (A).
(3) Statement I is incorrect but statement II is (3) (A) is correct but (R) is not correct.
correct. (4) (A) is not correct but (R) is correct.
(4) Both statements I and statements II are 15. Consider following molecule/ions as
correct. nucleophile or electrophile and select
13. Given below are two statements: incorrect statement.
(A) BF3
Statement-I : Alkyl group directly attached to

the negatively charged carbon destabilise it (B) H3C − C = O
due to inductive and hyperconjugation effect. (C) (CH3)3N
Statement-II : The observed order of (D) CO2
carbocation stability is : (1) A, B and D are electrophile
    (2) B is electrophile while A, C and D are
CH3  H3CCH2  (CH3 )2 CH  (CH3 )3 C
nucleophile.
In the light of the above statements, choose (3) A and B are electrophile while C is
the most appropriate answer from the nucleophile.
options given below: (4) Only C is nucleophile.
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 NEET : Chemistry
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16. Match the column :- 17. Match the column :- aaar

Column-I Column-II Column-I Column-II

(Organic compound) (Effect of (Functional (Effect)
substituent) group)
(a) NH2 (p) +I and +H (a) –OR (p) +M and –I
(b) O (q) +M and +I
–C–OH
(b) NO2 (q) –M and –I (c) –CH3 (r) +I and +H
(d) Θ (s) –M and –I
−O

(c) CH3 (r) +M and –I (1) a = q, b = s, c = r, d = p

(2) a = p, b = r, c = s, d = q
(3) a = p, b = s, c = r, d = q
(4) a = q, b = s, c = p, d = r
(d) CH3 (s) +I only
CH3–C–CH3

(1) a = p, b = q, c = r, d = s
(2) a = r, b = q, c = s, d = p
(3) a = r, b = q, c = p, d = s
(4) a = p, b = r, c = s, d = q

EXERCISE-III (Analytical Questions) ANSWER KEY

Question 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Answer 2 4 2 4 3 1 3 2 1 1 4 2 3 1 2
Question 16 17
Answer 3 3

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