TG: @Chalnaayaaar

ALLEN Pre-Medical : Chemistry 75

EXERCISE-I (Conceptual Questions) Build Up Your Understanding
ATTACKING REAGENT 7. Most stable carbanion is :-
1 1
(1) HC C (2) H2C CH
1. Which of the following species is an electrophile
(1) RNH2 (2) SO3 CH3
1 1
(3) NO3Q
(4) ROH (3) CH3–C CH2 (4) CH3–C CH
GC0001 CH3 CH3

2. Which of the following acts as a nucleophile? GC0007

Å
(1) N O2 8. The correct order of stability of given carbanions will
(2) :CCl2
be :-
Θ
(3) N H2 (4) · CH3 CH3–CH 2 CH 2=CH HC º C
(I) (II) (III)
GC0002 (1) I > II > III (2) III > II > I
REACTION INTERMEDIATES (3) I > III > II (4) II > I > III

3. Which of the following contains three pair of GC0008

electrons : 9. Which is most basic among the following :-
(1) Carbanion (2) Carbocation EN (1) CH3NH2
(3) Carbon free radical (4) None (2) CH3CH2NH2
GC0003 (3) NH3
(4) (CH3)2CHNH2
4. Carbanion is a :-
GC0009
(1) Base (2) Nucleophile
(3) Both the above (4) None 10. Which of the following has maximum pKa :-
LL
(1) CH2FCOOH (2) CH2ClCOOH
GC0004 (3) CH3COOH (4) HCOOH
I-EFFECT GC0010

5.
1 11. Which of the following show + I-effect :-
CH 3 is less stable than :-
(1) – OH (2) – OCH3 (3) – CH3 (4) – Cl
A

1 1
(1) CH3— CH2 (2) CH3— CH —CH3 GC0012
1 1 12. The strongest acid amongst the following compounds
(3) CH2 —NO2 (4) CH3— CH —C2H5
is ?
GC0005
(1) CH3CH2CH(Cl)CO2H
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6. Decreasing order of –I effect of the triad [–NO2, (2) ClCH2CH2CH2COOH

Å (3) CH3COOH
– NH 3 , –CN] is :-
(4) HCOOH
Å
(1) – NH 3 > –NO2 > –CN GC0014
Å
13. Which of the following acids is stronger than acetic
(2) – NH 3 > –CN > NO2
acid :-
Å
(3) –CN > –NO2 > – NH 3 (1) Propanoic acid (2) HCOOH
Å (3) Butyric acid (4) (CH3)2CHCOOH
(4) –NO2 > –CN > – NH 3
GC0015
GC0006

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76 Pre-Medical : Chemistry ALLEN

14. Which of the following acids have the lowest pKa 19. In which of the following compounds carbon–chlorine
value :- bond distance is minimum :-
Cl (1) CH3—Cl

(1) CH3 CH COOH (2) C6H5—CH2—Cl

(2) Cl CH2 CH2 COOH (3) CH2 CH—Cl

(3) CCl3COOH (4) CH2 CH—CH2—Cl

(4) CHCl2COOH GC0021

GC0016 20. Consider the following carbocations

Å Å
R- OR M-EFFECT (a) CH3O CH2 (b) CH2

15. Most stable carbocation is :- Å Å

(c) CH3 CH2 (d) CH3— C H2
Å Å Å Å
CH2 CH2 CH2 CH2 The relative stabilities of these carbocations are such
that :-
(1) (2) (3) (4) (1) d < b < c < a (2) b < d < c < a
(3) d < b < a < c (4) b < d < a < c
Cl NO2 OCH3 GC0022

16. Most acidic compound is :-

EN
GC0017 21. Among the following, the strongest base is :-

(1) C6H5NH2 (2) p–NO2–C6H4NH2

(1) OH (3) m–NO2–C6H4NH2 (4) C6H5CH2NH2

NGC0179
(2) CO2H
22. The most stable carbanion among the following is
LL
1 1
CH2 CH2 CH2
(1) (2)
(3) H3C CO2H

1 1
(4) O2N CO2H CH2 CH2
A

GC0018 (3) (4)

17. Which resonating structure of vinyl chloride is least
stable :- OCH3 NO2
. ..
(1) CH2 . ..
CH— Cl GC0025
23. The oxygen atom in phenol –
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(2) —CH (1) exhibits only inductive effect

(2) exhibits only resonance effect
(3) — —Cl (3) has more dominating resonance effect than
(4) All have equal stability inductive effect
(4) has more dominating inductive effect than
GC0019
resonance effect
18. The stabilization due to resonance is maximum in GC0027
24. Mesomeric effect is due to :-
(1) (2)
(1) Delocalization of s es–
(2) Delocalization of p es–
(3) (4) (3) Migration of H – atom
(4) Migration of proton
GC0020 GC0029

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ALLEN Pre-Medical : Chemistry 77

25. Which of the following is least basic :– 30. The correct order of acidic strength of the following
NH2 compounds is :-
A. Phenol B. p-Cresol
(1) (2) (3) (4)
C. m-Nitrophenol D. p- Nitrophenol
Cl (1) C > B > A > D (2) D > C > A > B
NGC0180 (3) B > D > A > C (4) A > B > D > C
GC0037
26. Among the following the aromatic compound is –
31. Which one of the following compounds is most
acidic:-
(1) (2) OH OH
(1) (2)
NO2 CH3

(3) (4) OH
(3) (4) ClCH2CH2OH

GC0032 GC0038
27. Which is aromatic compound among the following 32. Which of the following is most acidic :-

(1)
Å
(2)
EN (1) phenol
(3) m-chloro phenol
(2) benzyl alcohol
(4) cyclohexanol
GC0039
(3) (4) All the above 33. Which of the following is the strongest base :-
N
(1) (2)
LL
GC0033

28. Select the correct option for stability of following

carbanions : (3) (4)

CH3
CH3 ; C6H5CH2 ; CH3–C GC0040
A

(I) (II) CH3

(III) 34. Which is Aromatic compound :-
(1) I > II > III (2) II > I > III
(3) III > II > I (4) II > III > I
GC0034 (1) (2)
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29. The non aromatic compound among the following N

is :-
(3) (4) 2 and 3 both
N
(1) (2) NGC0181
S
35. Which of the following is the most acidic compound :-
(1) CH2 = CH2 (2) HC º CH
(3) (4)
(3) (4)

GC0036
NGC0182

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78 Pre-Medical : Chemistry ALLEN

36. Among the following the strongest acid is :- 41. Mark the correct order of decreasing acid strength
(1) CH3COOH of the following compounds.
(2) C6H5COOH
(3) m–CH3OC6H4COOH OH OH OH OH OH

(4) p–CH3OC6H4COOH
OCH3 NO2
NGC0183
NO2 OCH3
37. Which one of the following resonating structures of (a) (b) (c) (d) (e)
1–methoxy–1,3–butadiene is least stable :–
(1) e > d > b > a > c (2) b > d > a > c > e
(1) H2–CH=CH–CH= –CH3 (3) e > d > c > b > a (4) b > d > c > a > e

(2) CH2=CH– H–CH= –CH3 NGC0184

HYPERCONJUGATION
(3) H2– H–CH=CH–O–CH3
42. Which of the following compounds exhibits
(4) CH2=CH–CH=CH–O–CH3
hyperconjugation :
GC0046
(1) Phenol (2) Ethyne
38. Four structures are given in options (a) to (d). Examine (3) Ethanol (4) Propene
them and select the aromatic strucutures. EN GC0051

(a) (b) 43. Which of the following is least stable :–

(1)
(c) (d)
(2)
(1) a and d (2) b and c
LL

(3) a and b (4) a and c (3)

GC0047
39. Order of acidic strength of the following compound
will be : (4)
OH
A

OH
GC0052
(A) (B)
44. Which of the following is most stable alkene :-
CH3
OH (1)
OH
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(C) (D)
NO2 (2)
NO2
(1) C > D > B > A (2) D > C > B > A
(3) A > B > C > D (4) B > A > C > D (3)

GC0048

40. Phenol is less acidic than (4)

(1) Ethanol (2) o-Nitrophenol
(3) o-Methylphenol (4) o-Methoxyphenol GC0053
GC0049

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ALLEN Pre-Medical : Chemistry 79

TAUTOMERISM
45. Tautomerism is due to :- 47. Urea H2N–C–NH2 molecule exhibits (isomerism):-
O
(1) Delocalization of sigma electrons
(2) Delocalization of pi electrons
(1) Chain (2) Position
(3) Migration of active–H–atom
(3) Geometrical (4) Tautomerism
(4) None is correct
GC0057
NGC0185
46. Which of the following will lead to maximum 48. Tautomerism is not observed in :–
enolisation :–
O
(1)
(1) CH3–C–CH3

(2) CH3–C–CH2–C–H (2) Ph–CH=CH–OH

O O
(3) CH3–NO2
(3) CH3 C CH C CH3
O Br O
(4)
O
(4) EN
GC0056 GC0058
LL
A
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EXERCISE-I (Conceptual Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 2 3 2 3 3 1 1 2 4 3 3 1 2 3 3
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. 4 3 4 3 1 4 4 3 2 1 3 4 2 1 2
Que. 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
Ans. 1 3 4 4 4 3 3 4 1 2 4 4 2 2 3
Que. 46 47 48
Ans. 4 4 4
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80 Pre-Medical : Chemistry ALLEN

EXERCISE-II (Previous Year Questions) AIPMT/NEET
6. Given are cyclohexanol (I), acetic acid (II), 2, 4,
AIPMT 2006
6–trinitrophenol (III) and phenol (IV). In these the
1. Which of the following is more basic than aniline order of decreasing acidic character will be :-
(1) Diphenyl amine (2) Triphenyl amine (1) III > IV > II > I (2) III > II > IV > I
(3) p-nitro aniline (4) Benzyl amine (3) II > III > I > IV (4) II > III > IV > I
GC0061 GC0066
AIPMT 2007 AIPMT Mains-2010
2. Which of the following presents the correct order 7. Among the following four compounds :-
of the acidity in the given compounds :
(a) phenol (b) methyl phenol
(1) FCH2COOH > CH3COOH > BrCH2COOH
(c) metanitrophenol (d) paranitrophenol,
> ClCH2COOH
The acidity order is :
(2) BrCH2COOH > ClCH2COOH > FCH2COOH
(1) c > d > a > b (2) c > d > c > b
> CH3COOH
(3) b > a > c > d (4) d > c > a > b
(3) FCH2COOH > ClCH2COOH > BrCH2COOH
GC0067
> CH3COOH
8. Which of the following species is not electrophilic in
(4) CH3COOH > BrCH2COOH > ClCH2COOH
nature :-
> FCH2COOH Å
EN
GC0062 (1) BH3 (2) H3 O
Å Å
AIPMT 2008 (3) NO (4) Cl
2
3. The stability of carbanions in the following:-
GC0068
..
(a) RC 1 (b) AIPMT Mains-2011
C
9. Which of the following compounds is most basic ?
LL

(c) R 2C=CH (d) R 3C–CH2 (1) –NH2 (2) O2N– –NH2

is in the order of:-
(1) (d) > (b) > (c) >(a) (2) (a) >(c) >(b) >(d)
••
(3) (a) > (b) > (c) > (d) (4) (b) > (c) > (d) >(a) (3) –CH2NH2 (4)
••
–N–COCH3
GC0063
A

H
4. Basic strength of:-
1 1 GC0070
(a) H3C— CH2 — CH and
(b) H2C —
AIPMT Pre.-2012
1
—C
—
(c) HC — 10. The correct order of decreasing acid strength of
trichloroacetic acid (A), trifluoroacetic acid (B), acetic
is in the order of:-
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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
GC0064
GC0073
AIPMT 2010
NEET-UG 2013
5. Which one of the following compounds has the most
acidic nature ? 11. The radical, CH2· is aromatic because it
OH
CH2OH has :-
(1) CH (2)
(1) 6p–orbitals and 7 unpaired electrons
(2) 6p–orbitals and 6 unpaired electrons
OH OH
(3) (4) (3) 7p–orbitals and 6 unpaired electrons
(4) 7p–orbitals and 7 unpaired electrons
GC0065
GC0075
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ALLEN Pre-Medical : Chemistry 81

12. The order of stability of the following tautomeric 16. Which of the given compounds can exhibit
compounds is :- tautomerism?
OH O

=
–
CH2=C–CH2–C–CH3 CH3 CH3
CH3
(I)
CH3 CH3
O O
CH3
=

CH3–C–CH2–C–CH3 O O O
(II) (I) (II) (III)
OH O
(1) I and III (2) II and III
=
–

CH3–C=CH–C–CH3
(III) (3) I, II and III (4) I and II
(1) II > III > I (2) I > II > III GC0083
(3) III > II > I (4) II > I > III 17. Which of the following is the most correct electron
displacement for a nucleophilic reaction to take
GC0076
place?
AIPMT 2015
13. In which of the following compounds, C–Cl bond H H2
ionisation shall give most stable carbonium ion? (1) H3C C = C – C– Cl
H
H EN
H3C CH – Cl H H2
C – Cl (2) H3C C = C – C– Cl
(1) H3C (2) H
CH3
H H2
(3) H3C C = C – C– Cl
H
H H3C H
(3) C – Cl (4) C – Cl H2
H H
LL
O2NH2C H3C (4) H3C C = C – C– Cl
H
GC0080
GC0084
14. Consider the following compounds
Re-AIPMT 2015
CH3 Ph 18. Which of the following statements is not correct for
a nucleophile ?
A

CH3 – C – CH – Ph – C – Ph
– CH3 (1) Nucleophiles attack low e– density sites
CH3 (2) Nucleophiles are not electron seeking
(I) (II) (III) (3) Nucleophile is a Lewis acid
Hyperconjugation occurs In :- (4) Ammonia is a nucleophile
(1) II only (2) III only (3) I and III (4) I only GC0085
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GC0081 19. Correct order of Kb is

15. Given :-
CH2NH2 NH2
H3 C CH3 H3 C CH2 H2C CH2
(i) (ii)
CH3 CH3 CH2
(I) (II) (III)
(iii) CH3CH2–NH2 (iv) H3C C NH2
The enthalpy of the hydrogenation of these
O
compounds will be in the order as :-
(1) III > II > I (2) II > III > I (1) iv > iii > ii > i (2) iii > i > ii > iv
(3) II > I > III (4) I > II > III (3) i > ii > iii > iv (4) ii > iii > iv > i
GC0082 GC0086

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82 Pre-Medical : Chemistry ALLEN

23. Which among the given molecules can exhibit
NEET-I 2016
tautomerism ?
20. The correct statement regarding a carbonyl
co mpound with a hydrogen a tom on its O O
alpha carbon,is :-
O Ph
(1) a carbonyl compound with a hydrogen atom on
its alpha-carbon never equilibrates with its
Ph
corresponding enol. I II III
(2) a carbonyl compound with a hydrgen atom on (1) Both I and II
its alpha-carbon rapidly equilibrates with its (2) Both II and III
corresponding enol and this process is known (3) III only
as aldehyde-ketone equilibration.
(4) Both I and III
(3) a carbonyl compound with a hydrogen atom on
GC0092
its alpha-carbon rapidly equilibrates with its
24. The correct order of strengths of the carboxylic
corresponding enol and this process is known
acids
as carbonylation.
(4) a carbonyl compound with a hydrogen atom on COOH COOH COOH
its alpha-carbon rapidly equilibrates with its
corresponding enol and this process is known O O
as keto-enol tautomerism.
EN I II III
GC0089
21. The correct statement regarding the basicity of is
arylamines is :- (1) III > II > I (2) II > I > III
(1) Arylamines are generally less basic than (3) I > II > III (4) II > III > I
alkylamines because the nitrogen lone-pair GC0093
electrons are delocalized by interaction with the NEET(UG) 2017
aromatic ring p electron system. 25. Which one is the correct order of acidity ?
LL

(2) Arylamines are generally more basic than (1) CH º CH > CH3 – C º CH > CH2 = CH2 >
alkylamines because the nitrogen lone-pair
CH3 – CH3
electrons are not delocalized by interaction with
(2) CH º CH > CH2 = CH2 > CH3 – C º CH >
the aromatic ring p electron system.
CH3 – CH3
(3) Arylamines are generally more basic than
(3) CH3 – CH3 > CH2 = CH2 > CH3 – C º CH >
A

alkylamines because of aryl group.

(4) Arylamines are generally more basic than CH º CH
alkylamines, because the nitrongen atom in (4) CH2 = CH2 > CH3 – CH = CH2 > CH3 – C º
arylamines is sp-hybridized. CH > CH º CH
GC0090 GC0094
NEET-II 2016 26. Which one is the most acidic compound ?
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22. In pyrrole OH OH
4 3
(1) (2)

5 NO2
.. 2

N1
H OH OH
O2N NO2
The electron density is maximum on :- (3) (4)
(1) 2 and 4 (2) 2 and 5 NO2 CH3
(3) 2 and 3 (4) 3 and 4
GC0091 GC0095

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ALLEN Pre-Medical : Chemistry 83

27. The correct increasing order of basic strength for NEET(UG) 2019
the following compounds is :
30. The correct order of the basic strength of methyl
NH2 NH2 NH2 substituted amines in aqueous solution is :-

(I) (II) (III) (1) (CH3)2NH > CH3NH2 > (CH3)3N

CH3 (2) (CH3)3N>CH3NH2 > (CH3)2NH

NO2
(3) (CH3)3N>(CH3)2NH>CH3NH2
(1) III < I < II (2) III < II < I
(3) II < I < III (4) II < III < I (4) CH3NH2>(CH3)2NH > (CH3)3N
GC0096 GC0170
28. The correct statement regarding electrophile is :- 31. The compound that is most difficult to protonate is:-
(1) Electrophile is a negatively charged species and O
can form a bond by accepting a pair of electrons (1)
H H
from another electrophile
O
(2) Electrophiles are generally neutral species and (2) H C H
3
can form a bond by accepting a pair of electrons
from a nucleophile O
(3) H C CH3
3
(3) Electrophile can be either neutral or positively
charged species and can form a bond by EN (4) O
Ph H
accepting a pair of electrons from a nucleophile
(4) Electrophile is a negatively charged species and GC0171
can form a bond by accepting a pair of electrons NEET(UG) 2019 (ODISHA)
from a nucleophile 32. The most stable carbocation, among the following
GC0097 is :-
NEET(UG) 2018 Å
(1) (CH3)3C–CH–CH3
LL
29. Which of the following is correct with respect to
–I effect of the substituents ? (R = alkyl) Å
(1) – NH2 < – OR < – F (2) CH3–CH2–CH–CH2–CH3
(2) –NR2 < – OR < – F Å
(3) CH3–CH–CH2–CH2–CH3
(3) – NH2 > – OR > – F Å
(4) – NR2 > – OR > – F (4) CH3–CH2 –CH2
A

GC0101 GC0172
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EXERCISE-II (Previous Year Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 4 3 3 2 3 2 4 2 3 3 2 3 2 2 1
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. 3 2 3 1 4 1 2 3 4 1 3 3 3 1 1
Que. 31 32
Ans. 4 3
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84 Pre-Medical : Chemistry ALLEN

EXERCISE-III (Analytical Questions) Master Your Understanding

1. Which hydrogen in the following hydrogen is most 4. The correct order of decreasing basic strength is
acidic :-
NH2

CH3–CH 2–CH2–C–H
I II III IV
N N
(1) C1–H (2) C2–H N
H H
(3) C3–H (4) C4–H
(1) I > II > III > IV (2) II > III > I > IV
GC0109 (3) II > IV > I > III (4) II > III > IV > I
NGC0188
2. Which of the following has the most acidic proton:
5. Select the correct option for stability of following
O
resonance structures :-
(1) CH3–C–CH3

Å Å
O O CH2 , O CH2 , O CH2
(2) CH3–C–H EN x y z
(3) CH3–C–CH2–C–CH3
(1) x > y > z (2) z > y > x
O O
(3) y > x > z (4) y > z > x
NGC0189
O
LL
C–CH3 6. (a) CH2 CH—CH CH2
(4) CH3–C–CH–C–CH3 (b) CH3—CH CH2
O O (c) CH3—CH3
C—C single bond distance would be :-
NGC0186
(1) a < b < c
A

3. Which is not aromatic compound :- (2) a > b < c

(3) a < b > c
: :

O
O (4) a < b > c
(1) (2)
Å O NGC0190
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7. Which is wrong electromeric effect :

Å
(3) (4) (1) C=O C–O

Å
(2) CH3–CH=CH2 CH3–CH–CH2
NGC0187 Å
(3) –CºN –C=N
Å
(4) CHºCH CH=CH
GC0118

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ALLEN Pre-Medical : Chemistry 85

8. Tautomerism is exhibited by :- 11. The correct order of stability of following carbon free
O radical is :-
CH3 CH3 O ·
(1) CH CH3 (2) CH3–CH2–N
3 O (CH 3 )3 C CH2
(1)
O CH=O (2)
· ·
(3) (4) CH 3CH 2 CH 2 CH 3
O (3) (4)
GC0119
9. Identify the compound that exhibits tautomerism :- (1) 1 > 2 > 3 > 4
(1) 2-Pentanone (2) Formaldehyde
(3) 2-Butene (4) Lactic acid (2) 4 > 3 > 2 > 1
GC0120 (3) 2 > 3 > 1 > 4
10. Arrange the following in correct order of acidic
(4) 2 > 1 > 3 > 4
strength :
(I) CH3—NO2 (II) NO2—CH2—NO2 GC0122

(III) CH3—CH2—NO2 (IV) NO2 CH NO2

NO2 EN
(1) IV > II > I > III (2) IV > II > III > I
(3) III > I > II > IV (4) III > I > IV > II
GC0121
LL
A
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EXERCISE-III (Analytical Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11
Ans. 2 4 2 4 3 1 3 2 1 1 4
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Pre-Medical : Chemistry

A
LL
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IMPORTANT NOTES

EN
ALLEN

E
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