Exercise - I: (Only One Option Is Correct)

GOC Page # 27
Exercise - I (Only one option is correct)
1. Bond formation is: 4. In which of the following molecules – NO2 group is

not coplanar with phenyl ring ?
(A) always exothermic
CH3 CH3
(B) always endothermic
(C) neither exothermic nor endothermic
(A) (B)
(D) sometimes exothermic and sometimes endot-
N
hermic N O O
O O
Sol.
2. CH2 = CH – CN
3 2 1
(C) (D)
C1 - C2 bond of this molecules is formed by: I I N O
N
(A) sp3-sp2 overlap (B) sp2-sp3 overlap O O O
(C) sp2-sp overlap (D) sp2-sp2 overlap Sol.

Sol.
3. In which of the following molecules resonance 5. In which of the following molecels both phenyl
takes place through out the entire system rings are not coplanar ?
CH3 CH3
O
(A) (B)
(A) (B)
CH3 CH3
(C)
CH3
NH
CH3
COOCH3
(D) | (E)
COOCH3
CH3 CH3
(C) (D) CH3 CH3
Sol.
CH3
Sol. CH3
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Page # 28 GOC
6. In which of the following molecules, all atoms are 9. Rank the following compounds in order of decreas-
not coplanar ? ing acidity of the indicated hydrogen :
O O O
O O
CH3CCH2CH2CCH3 CH3CCH2CH2CH2CCH3
(A) (B)
O
O O O
O CH3CCH2CCH3
(A) I > II > III (B) III > I > II

(C) (D)
(C) I > III > II (D) III > II > I
O
Sol.
Sol.
O O O
7. (I) CH3 – CH = O (II) CH2 = CH – OH || | |
10. H C C C
OH H OH H OH
(II) CH 3 – CH – O
I II III
Among, these, which are canonical structures ?
Among these canonical structures, the correct
(A) I and II (B) I and III
order of stability is
(C) II and III (D) all
(A) I > II > III (B) III > II > I
Sol.
(C) I > III > II (D) II > I > III
Sol.
11. (I) CH2 = CH – CH = CH – OCH3
8. (I) CH2 = CH – CH = CH2 (II) CH2 – CH = CH – CH = OCH3
(II) CH2 – CH = CH – CH2 (III) CH2 = CH – CH – CH – OCH3
(II) CH2 – CH = CH – CH2 (IV) CH2 = CH – CH – CH – OCH3
Among, these, which are canonical structures ? Amongt these canonical structures which one is
least stable ?
(A) I and II (B) I and III
(A) I (B) II
(C) II and III (D) all
(C) III (D) IV
Sol.
Sol.
12. CH2 = CH – CH = CH – CH3 is more stable than CH3
– CH = C = CH – CH3 because
(A) there is resonance in I but not in II
(B) there is tautomerism in I but not in II
(C) ther is hyperconjugation in I but not in II
(D) II has more cononical structures than I.
GOC Page # 29
Sol.
O=N N=O
(C)
13. For phenol which ofthe following resonating struc-
ture is the most stable ?
OH
OH (D) O – N N=O
(A) (B) Sol.
16.
OH
N N N N
(C) (D) All haveequal stability

I II III IV
Sol.
14. (I) CH3 – O – CH = CH – CH = CH2
N
(II) CH – O – CH – CH = CH – CH V
3 2
Among these canonical structures of pyridiine, the

(III) CH – O = CH – CH = CH – CH correct order of stability is
3 2
Among these three canonical structures (through (A) (I = V) > (II = IV) > III
more are possible) what would be their relative (B) (II = IV) > (I = V) > III
contribution in the hybrid
(C) (I = V) > III > (II = IV)
(A) I > II > III (B) III > II > I
(D) III > (II = IV) > (I = V)
(C) I > III > II (D) III > I > II
Sol.
Sol.
15. The most stable resonating structure of following
compound is 17.
N N N
..
O=N
..N = O H
|
H
|
H
|
(I) (II) (III)
..
(A) O = N N=O
N N
| |
H H
(IV) (V)
(B) O – N N–O
(A) (III = IV) > (II = V) > I
(B) I > (II = V) > (III = IV)
(C) I > (III = IV) > (II = V)
(D) (II = V) > (III = V) > I
Page # 30 GOC
Sol. Sol.
O O O
18.
N N N
| | | 22. In which of the following molecules π-electron
H H H density in ring is minimum?
(I) (II) (III)
NO2 OCH3
(A) (B)
The least stable canonical structure among these
is
NO2
(A) I (B) II (C) III
NO2
(D) all are equally stable
(C) (D)
Sol.
H2N NO2
19. Rank the following compounds in order of decreas-
ing acidity. Sol.
23. In which of the following molecules π-electron
density in ring is maximum?
(I) (II) (III)
(A) III > II > I (B) I > II > III NO2 O
(C) III > I > II (D) I > III > II (A) (B)
Sol.
NH2 OCH3
m o
(C) (D)
p OH
20.
m o Sol.
In phenol, π-electron-density is maximum on 4
(A) ortho and meta positions (B) ortho and para 24.
3 O
1
positions 2
(C) meta and pera positions (D) none of these

In this molecules, π-electron-density is more on
Sol.
(A) C1 and C3 (B) C2 and C4
21. Which of the following compounds has maximum (C) C2 and C3 (D) C1 and C4
electron density in ring ?
Sol.
NO2 OH
(A) (B)
25. In which of the following pairs, first species is

O COO more stable than second ?
(C) (D) O
–
(A) CH3CH2O– or CH3CO
GOC Page # 31
O O O O O O
(B) CH 3CCHCH 2CH or CH3CCHCH3
(III) (IV)
O O
(C) CH 3CHCH 2CCH 3 or CH 3CH 2CHCCH 3 Among these compounds, which one has maxi-
mum resonance energy ?
O O (A) I (B) II
(C) III (D) IV
–
(D) N or N– Sol.
Sol.
26. CH3COOH CH3COONa CH3CONH2
(I) (II) (III) 1 1 1
2 2 2
Among these compounds, the correct order of 29. 3 3 3
resonance energy is 4 4 4
(A) I > II > III (B) III > II > I There are thre e canoni cal st ruct ures of
(C) II > III > I (D) II > I > III napthalene. Examine them and find correct state-
Sol. ment among the following:
27. Rank the following free radicals in order of de- (A) All C–C bonds are of some length
creasing stability (B) C1-C2 bond is shorter than C2-C3 bond.
(C) C1-C2 bond is longer than C2-C3 bond
(I) C6H5 CHC6H5
(D) None.
(II) C6H5 – CH – CH = CH2 Sol.
(III) CH3 – CH – CH3 (IV) C6H5 – CH – CH3
(V) CH3CH CHCH2 CH2
(VI) CH3 – CH2 – C – CH3 30. Which of the following has longest C – O bond:
CH3 O O
(A) I > II > IV > VI > III > V (A) (B)

(B) VI > V > IV > III > II > I
O
(C) I > II > III > IV > V > VI O
(D) I > IV > VI > V > II > III (C) (D)
Sol. CH2
Sol.
O O
28. (I) (II)
Page # 32 GOC
NH2 34. In which of the following molecules resonance

NH2 structutres are equivalent
(A) HCOOΘ
31. (I) (II)
(B) CH2 = CH – CH = CH2
CHO
NH2 CHO
(C) (D)
(III) (IV) CH2 = NH NH2
Sol.
Among these compounds, the corect order of
C – N bond length is :
(A) IV > I > II > III (B) III > I > II > IV
(C) III > II > I > IV (D) III > I > IV > II
Sol. 35. H – O – C =N H–N=C=O
(Cyanic acid) (Isocyanic acid)
Loss of proton from these two acids produces
(A) same anion (B) different anions
(C) same cation (D) different cations
32. C1 – C2 bond is shortest in
Sol.
2 2
CH = CH2
1 1
(A) (B)
2 2
CH2 – CH3
1 1
(C) (D)
36. (I) (II) (III)
Sol.
Which of these cyclopropene systems is aromatic
(A) I (B) II
(C) III (D) all of these
Sol.
33. Among the following molecules, the correct order
of C - C bond length is
(A) C2H6 > C2H4 > C6H6 > C2H2
(B) C2H6 > C6H6 > C2H4 > C2H2 (C6H6 is benzene) 37. (I) (II) (III)
(C) C2H4 > C2H6 > C2H2 > C6H6

(D) C2H6 > C2H4 > C2H2 > C6H6 Which of these species is anti-aromatic ?
Sol. (A) I only (B) II only
(C) III only (D) both II and III
Sol.
GOC Page # 33
38. Which of the following compouds is not aromatic
O O O
(A) (B) (C) (D)

O O
O
O
(C) (D)
O Sol.
O
Sol.
41. Which of the following statements would be true

about this compound:
NO2
39. N=N 5
The most stable canonical structure of this mol- 1 3

ecule is NO2 NO2
Br
(A) All three C – N bonds are of same length.
(A) N=N (B) N=N
(B) Cl – N and C3 – N bonds are of same length
but shorter than C5 – N bond
N=N (C) Cl – N and C3 – N bonds are of same length

(C)
but longer than C5 – N bond
(D) Cl – N and C3 – N bonds are of different
(D) All are equally stable
length but bot are longer than C5 – N bond.
Sol.
Sol.
40. 42. Ease of ionization to produce carbocation and bro-

O m i d e i o n u n
⊕
will be maxi-
d e r t h e t r e a t m e n t o f A g
mum in whichof the following compounds ?

The most stable canonical structure of this mol-
ecule is
Br
Br
(A) (B)
O O OCH3
(A) (B)
Page # 34 GOC
Br K
Br
(C) (D) 45. P will be
OCH3 BuLi
P
Sol.
(A) (B)
(C) mixture of (A) & (B) (D) none of these
43. Ease of ionization to produce carbocation and bro- Sol.

mide ion under the treatment of Ag⊕ will be maxi-
mum in whichof the following compounds ?
Br Br
(A) (B)
Br
(C) (D)
OCH3 Br
46. (I) (II) (III)

Sol.
The barrier for rotation about the indicated bonds

Cl will be maximum in which of these three com-
44. 2SbCl5 P will be pounds ?
Cl (A) I (B) II
(C) III (D) same in all
Sol.
(A) 2– (B) 2+ 2SbCl6
47. (I) (II) (III)

O N
(C) |
H
(D) mixture of (a) and (b) The aromatic character is maximum in which of
these three compounds ?
Sol.
(A) I (B) II
(C) III (D) same in all
Sol.
GOC Page # 35
48. Find out the hybridisation state of carbon atoms

in given compounds from left to right.
C H
3
– CH = CH – CH = C = CH – C ≡ C – CH3
CMe3
(A) sp3 sp2 sp2 sp2 sp sp2 sp sp sp3 (IV)
(B) sp3 sp2 sp2 sp sp sp sp sp sp3
Me
Me
3 2 2 2
(C) sp sp sp sp sp sp sp sp sp 2 2 3
(D) sp3 sp sp sp2 sp sp2 sp sp sp3

(A) I > II > III > IV (B) III > II > I > IV
Sol. (C) III > I > II > IV (D) III > II > IV > I
Sol.
49. Total number of σ and π-bonds are in naphtha-
lene is
(A) 5π and 18σ (B) 6π and 19 σ
(C) 5π and 19σ (D) 7π and 26σ
Sol.
50. Writecorrect order of stability of following

carbocations:
51. The abstraction of proton will be fastest, in which

(I) CMe3
carbon in the following compound
Me
Me
O
y
z p
x
H3C CH3
(A) x (B) y
(II) CMe3 (C) z (D) p
Me
Me Sol.
52. Number of π-electron in (C4H4)2– is
(III) CMe2 (A) 2 (B) 4

Me (C) 6 (D) 8
Sol.
Page # 36 GOC
53. Identify the odd species out Which of the spe- (A) I > II > III (B) I > III > II
cies among the following is different from others ? (C) III > II > I (D) II > III > I
Sol.
(A) (B)
(C) (D) 56. Which one of the following statements is True:
Sol.
(1) (2)
(A) PhLi adds to both compound with equal ease

54. Which one of the following carbonyl compound (B) PhLi does not add to either of the compound
when treated with dilute acid forms the more (C) PhLi react readily with 1 but does not add to 2
stable carbocation ? (D) PhLi react readility with 2 but does not add to 1
O Sol.
||
(A) CH3 – C – CH3 (B)
57. Correct order of rate of hydrolysis or rate of re-

CH3
action toward AgNO3 for following compounds is
HO O
||
(C) (D) C6H5 – C – C6H5
Br
HO OH
O
(I)
Sol.
Br
(II)
55. The order of the rate of formation of carbocations
from the following iodo compound is:
(I) (II) (III)

H I H I H I
GOC Page # 37
60. Arrange the following carbocations in the increas-

Br ing order of their stability.
Br
(III) (IV)
(I) (II)
(A) III > II > IV > I (B) I > II > III > IV
(C) III > I > II > IV (D) III > II > I > IV
Sol.
(III)
(A) I > II > III (B) I > II = III

(C) I > III > II (D) III > I > II
Sol.
58. Write correct order of reactivity of following halo-

gen derivatives towards AgNO3.
Cl
61. Which of the following carbocation will be more
(I) (II) CH2 = CH – Cl (III) Et3 C – Cl stable ?
O
(A) +
H 3C CH CH3
(IV) PhCH2Cl (V) Ph3C – Cl
(A) I > V > IV > III > II CH3
(B) +
(B) V > IV > I > III > II H 3C CH
(C) V > I > IV > III > II

CH3
(D) I > V > III > IV > II +
(C) H C + H3C C
Sol. 3 CH CH3 (D)
CH3
Sol.
62. Statement-1: Me – CH is more stable than MeO

2
59. Which of the following heterocyclic compounds – CH2

would have aromatic character ? Statement-2: Me is a +I group where as MeO is
a –I group.
N N
(A) (B) N–H (A) Statement-1 is true, statement-2 is true and
N statement-2 is correct explanation for statement-
1.
N–H (B) Statement-1 is true, statement-2 is true and
(C) (D) N–H
N–H statement-2 is NOT correct explanation for state-
ment-1.
Sol.
(C) Statement1 is false, statement-2 is true.
(D) Statement1 is true, statement-2 is false.
Sol.
Page # 38 GOC
66. Which of the following is the strongest base

CH3
63. When – CH3, CH3 – CH – and CH3 – C – groups NH2 NHCH3

(A) (B)
CH3 CH3
are introduced on benzene ring then correct or-

der of their inductive effect is NH2
(C) (D) CH2NH2
CH3 CH3
(A) CH3 – > CH3 – CH – > CH3 – C – Sol.
CH3 CH3
CH3
67. Amongst the following the most basic compound
(B) CH3 – C – > CH3 – CH – > CH3 – is
CH3 CH3 (A) Aniline (B) Benzylamine
(C) p-nitroaniline (D) Acetanilide
CH3 Sol.
(C) CH3 – CH – > CH3 > CH3 – C –
CH3 CH3
CH3
68. The increasing order of stability of the following
(D) CH3 – C – > CH3 – > CH3 – CH – free radicals is
CH3 CH3 (A) (C6H5)3C < (C6H5)2CH < (CH3)3C < (CH3)2CH
Sol.
(B) (C6H5)2CH < (C6H5)3C < (CH3)3C < (CH3)2CH
64. The correct order of increasing basic nature of
the bases NH3, CH3NH2 and (CH3)2NH is gas phase (C) (CH 3)2CH < (CH3)3C < (C 6H5)3C < (C6H5)2CH
(A) NH3 < CH3NH2 < (CH3)2NH

(D) (CH3)2CH < (CH3)3C < (C6H5)2CH < (C6H5)3C
(B) CH3NH2 < (CH3)2NH < NH3
(C) CH3NH2 < NH3 < (CH3)2NH Sol.
(D) (CH3)2NH < NH3 < CH3NH2 69. The correct order of increasing acid strength of
the compounds
Sol.
65. Consider the acidity of the carboxylic acids ( a ) C H CO2H
3
(b) MeOCH2CO2H
Me
(a) PhCOOH (b) o–NO2C6H4COOH (c) CF3CO2H (d) CO2H
Me
(c) p-NO2C6H4COOH (d) m-NO2C6H4COOH
(A) d < a < c< d (B) d < a < b < c
Which of the following order is correct ? (C) a < d < c < b (D) b < d < a < c
(A) a > b > c > d (B) b > d > c > a Sol.
(C) b > d > a > c (D) b > c > d > a
Sol.
GOC Page # 39
70. Which one of the following is the strongest base

in aqueous solution ?
(I) (II)
(A) Trimethylamine (B) Aniline
(C) Dimethylamine (D) Methylamine
Sol.
(III) (IV)
(A) III > II > I > IV (B) III > IV > I > II
(C) II > III > I > IV (D) IV > II > I > III
71. Arrange the carbonions,
Sol.
(CH3)3C, CCl3, (CH3)2CH, C6H5CH2 in order of their
75. Arrange in decreasing pKb
decreasing stability
(a) F – CH2CH2 COOH
(A) (CH 3)2CH > CCl3 > C6H 5CH 2 > (CH 3)3C
(b) Cl – CH – CH2 – COOH
(B) CCl3 > C 6H 5CH2 > (CH3)2CH > (CH 3)3C
Cl
(C) (CH 3)3C > (CH 3)2CH > C 6H 5CH 2 > CCl3
(c) F – CH2 – COOH
(D) C6H5CH2 > CCl3 > (CH3)3C > (CH3)2CH
(d) Br – CH2 – CH2 – COOH
Sol. Correct answer is
72. Consider the following carbanions (A) b > d > a > c (B) a > c > d > b
(C) c > b > a > d (D) d > b > a > c
(i) CH3 – CH2 (ii) CH2 = CH
Sol.
(iii)
Correct order of stabilityof these carboanions in
decreasing order is
(A) i > ii > iii (B) ii > i > iii
(C) iii > ii > i (D) iii > i > ii 76. Which of the following species is not aromatic ?
Sol.
73. The order of stability of the following carbanion
(A) (B)
is
O O
(I) CH3CH2 (II)

(C) (D)
(III) (IV)
Sol.
(A) I > II > III > IV (B) I > III > II > IV
(C) IV > III > II > I (D) III > IV > I > II
77.
Sol. N
74. Rank thefollowing radicals in order of decreasing

Nitrogen atom of pyridine is
stability
(A) sp3 hybridized (B) sp2 hybridized
(C) sp hybridized (D) Not hybridized
Page # 40 GOC
78.
O 81. HClO4 P will be
Oxygen atom of furan is
O
(A) sp3 hybridized (B) sp2 hybridized
(C) sp hybridized (D) Not hybridized
Sol.
79. Ease of ionization to produce carbocation and ClO4 H
bromide ion under the treatment of Ag⊕ will be (A) (B)
maximum in which of the following compounds?
OH OH
O
(A) O (B)
Br Br
H
N Br
(C) N Br (D) (C) ClO4 (D) Mixture of (A) & (B)
CH3
Ph O
Sol.
Sol.
80. (I) (II) (III) 82. Cl

Ag ClO4 P
O N
|
H
Which of the following choice is the correct (A) ClO4 (B) Ag

order of resonance energy of these molecules ?
(A) I > II > III (B) II > I > III (C) Mixture of (A) & (B) (D) None of these
(C) III > II > I (D) III > I > II Sol.
Sol.
83. Which can lose a proton more readily, a methyl

group bonded to cyclohexane or a methyl group
bonded to bezene ?
(I) CH3 (II) CH3
(A) I > II (B) II > I

(C) equal (D) None
GOC Page # 41
Sol. 88. Contribution of second resonating structure is

more than first ?
(A) CH3CH = CHCH2+ or CH3CH+CH = CH2
CH3 CH3
84. (I) (II) (III) +
(B) or
Among these aromatic compounds the correct +
order of resonance eneergy per ring is
(A) I > II > III (B) III > II > I O O–
(C) III > I > II (D) II > I > III
–
Sol. (C) or
(D) All of these

85. (I) (II)
Sol.
Which of the following orders is correct for the

resonance energy of these two compounds ?
(A) I > II (B) II > I
(C) I = II
(D) there is nothing like π-electron energy
89. (I) (II) (III)
Sol.
O N
N
86. (I) (II) |
H
Which of the following order is correct for the
resonance energy of these two compounds ? The aromatic character is maximum in which of
these three compounds ?
(A) I > II (B) II > I
(A) I (B) II
(C) I = II
(C) III (D) Same in all
(D) there is nothing like π-electron energy
Sol.
Sol.
87. (I) CH = CH – CH (II)

2 2
Which of the following order is correct for More than one Correct
resonance energy of these cation 90. Which of the following is a 2° Amine ?
(A) I > II (B) II > I
(C) I = II (A) C – C – C – C (B) N
H
(D) there is nother like π-election energy NH
Sol. NH2
N
(C) (D)
Page # 42 GOC
Sol. (c) CH2 = CH – O – CH = CH2

91. Identify electron - withdrawing groups in reso-
nance among the following: CH2
(a) – COOH (b) – CONHCH3 (d) CH2 = CH – C ≡ N (e)
(c) – COCl (d) – CN O
(e) – O – CH = CH2 (f)

N (f)
O
Sol.
Sol.
92. Identify electron - donating groups in resonance
among the following:
(a) – CONH2 (b) – NO2
(c) – OCOCH3 (d) – COOCH3
(e) – CHO (f) – NHCOCH3 95. Aromatic compounds are:
Sol.
N O
93. In which of the following lone-pair indicated is
involved in resonance : (A) (B)
N
N
(a) (b) N (C) (D)

N | B
H |
H
Sol.
(c) (d) N
N |
H 96. Which of the following reactions give aromatic
compound ?
(e) CH2 = CH – CH2–
O
••
(f) CH2 = CH - CH = N H KH
(A) (B) HBr
Sol.
O
HI
(C) (D) HBr
94. In which of the following lone-pair indicated is

not involved in resonance :
(a) CH2 = CH – N H – CH3
(b) CH2 = CH – CH = O
GOC Page # 43
Exercise - II
1. In which of the following molecules resonance
takes place through out the entire system.
(I)
(A) CH3CH2NHCH2CH = CH2
NH2 2. Which of the following pairs of structures are

resonance contributors ?
(B)
O O
(A) and
CH2NH2
(C) (B) CH3CH = CHCHCH = CH2 and

CH3CHCH = CHCH = CH2
(D) CH2 = CHCH2CH = CH2 O O

(C) CH CCH CH and
3 2 3 CH3C=CHCH3
CH2
(E) (D) and
3. Consider structural formulas A, B and C:

(F)
(A) (B) (C)
(G)
(a) Are A, B and C constitutional isomers, or are
they resonance forms?
(b) Which structures have a negatively charged
CH3 carbon?
(H) CH3CCH2CH = CH2 (c) Which structures have a positively charged
carbon?
(d) Which structures have a positively charged
Page # 44 GOC
nitrogen?
⊕ ⊕
(e) Which structures have a negatively charged (a) (I) C6H5– CH 2 and (II) CH2=CH– CH 2
nitrogen?
⊕ ⊕
(f) What is the net charge on each structure? (b) (I) CH3– CH 2 and (II) CH2 = CH
(g) Which is a more stable structure, A or B? Why?
(h) Which is a more stable structure, B or C? Why?
4. In each of the following pairs, determine (c) (I) and (II)
whether the two represent resonance forms
of a single species or depict different sub-
stances. If two structures are not resonance (d) (I) CH 3 − CH − CH 3 and
froms, explain why. |
CH 3 − C − CH 3
(a) and ⊕
(II) CH 3 − N − CH 3
|
(b) and CH 3 − C − CH 3
⊕
Sol.
(c) and 8. Draw the resonance forms to show the delo-
calization of charges in the following ions
O
5. Determine the hybridization around the indi- (a) CH3– C – CH2
cated atom in the following anion.
O
(b) H – C – CH = CH – CH2
CH3 = CH – CH – CH3
(A) (B)
O
+
(c) CH2 (d)
+
O CH2
(C) CH3 – C (D) (e) O¯ (f) + NH
O
Sol. + ¯
6. Using hybridization, predict how the bond (g) (h)
legnth of the C – C σ bond in HC ≡ C – C ≡ CH O
should compare with the C – C σ bonds in O
CH3CH3 and CH2 = CH – CH = CH2.
Sol. +
(i) CH3 – CH = CH – CH = CH – CH – CH3
+
(j) CH3 – CH = CH – CH = CH – CH 2
7. In each of the following pairs of ions which ion (k) CH2 = CH – CH – CH = CH2
is more stable:
GOC Page # 45
11. Use resonance theory to explain why both C –

O O bond lengths are equal in the acetate anion.
C CH3
(l) CH3CH2 C O
equal bond lengths
CH3 – C
H
acetate O
+ Sol.
+
(m) CH3 – CH – Cl (n)
Sol.
9. Draw a second resonance structure and the
hybrid for each species, and then rank the
two resonance strcutures and the hybrid in
order of increasing stability
O
12. In the following sets of resonance forms, label
(A) (CH3)2 – C – NH2 (B) C
the major and minor contributors and state
CH3 NH
which structures would be of equal energy.
Sol. Add any missing resonance forms.
(a) CH3—CH–C≡N CH3—CH=C=N
O¯ O¯
+
(b) CH —C=CH–CH—CH
3 3 CH3—C—CH=CH—CH3
+
O O O¯ O
(c) CH —C–CH–C—CH CH3—C=CH–C—CH3
3 3
10. For acetic acid (CH3CO2H): (a) Draw three reso-

(d) [CH3 – CH – CH = CH – NO2 CH3 – CH = CH – CH – NO2]
nance structures; (b) draw a structure for the
resonance hybrid;s (c) rank the three reso-
nance structures and the resonance hybrid in NH2 NH2
order of increasing energy. (e) CH —CH —C—NH +
3 2 2 CH3—CH2—C = NH2
Sol. +
Sol.
Page # 46 GOC
13. From each set of resonance structure that fol-

low, designate the one that would contribute
most to the hybrid and explain your choice.
(c)
CH3 CH3
(a) CH3CH2C = CH – CH2 CH3CH2C – CH = CH2
⊕ Θ
(d) C H − CH = CH − O ←
→ CH 2 = CH − CH = O
(i) (ii) 2
(e)
CH2 CH2
(b) Sol.
15. Identify less stable canonical structure in
each of the following pairs :
(i) (ii)
⊕ ⊕
(a) C H − O − CH ←
2 3 → CH 2 = O − CH 3
(c) CH – N(CH ) CH2 = N(CH3)2 (b)

2 3 2
(i) (ii)
(c)
O O
(d) CH2 – C – O – H CH2 – C = O – H
(i) (ii) (d)
(e) : NH2 – C ≡N NH 2 = C = N (e)

(i) (ii)
14. Identify more stable canonical structure in each Sol.

of the following pairs :
O OΘ
(a) C .. C ⊕
H OH H OH 16. Which of the following statements is (are) true
about resonance.
(a) Resonance is an intramolecular process.
(b) (b) Resonance involves delocalization of both σ
and π electrons.
(c) Resonance i nvol ves del ocali zation of π
electrons and lone pair only.
GOC Page # 47
(d) Resonance decreases potential energy of a atom.

molecule. 19. Which of the following pairs has higher
(e) Resonance has no effect on the potential resonance energy:
energy of a molecule. (a) CH3COOH and CH3COONa
(f) Resonance i s the onl y way to increase
(b) CH2 = CH – O and CH2 = CH – OH
molecular stability.
(g) Resonance is not the only way to increase COO O
molecular stability. (c) and
(h) Any resonating molecule is always more stable
than any nonresonating molecule.
(i) The canonical structure explains all features
of a molecule. (d) and
(j) The resonance hybrid explains all features of a
molecule.
(k) Resonating structures are real and resonance (e) and CH2 = CH – CH = CH – CH = CH2
hybrid is imaginary.
(l) Resonance hybrid is real and resonating
Sol.
structures are imaginary.
(m) Resonance hybrid is always more stable than
all canonical structures.
Sol.
20. Which of the following pairs has less reso-
nance energy:
17. Resonance energy will be more if
(a) CO32– and HCOO–
(a) canonical structures are equivalent than if
canonical structures are non-equivalent.
(b) molecule is aromatic than if molecule is not (b) and CH2 = CH – CH2–
aromatic.
Sol.
(c) and CH2 = CH – CH = CH2

18. A canonical structure will be more stable if
(a) it has more number of π bonds than if it has
less number of π bonds.
(d) and CH2 = CH – CH2+
(b) the octets of all atoms are complete than if
octets of all atoms are not complete.
Sol.
(c) it involves cyclic delocalization of (4n + 2) π –
el ec trons than i f i t i nv ol ve s ac yc l i c
de l ocal i zati on of
(4n + 2) π – electrons.
(d) it involves cyclic delocalization (4n) π – 21. Which of the following pairs has higher
el ec trons than i f i t i nv ol ve s ac yc l i c resonance energy :
delocalizationof (4n) π – electrons.
(e) +ve charge is on more electronegative atom (a) and
than if +ve charge is on less electronegative
atoms.
(f) –ve charge is on more electronegative atom
than if –ve charge is on less electronegative (b) and
Page # 48 GOC
•
(c) and (d) and CH2 = CH – C H 2
(d) CH2 = CH – OH and CH2 = CH – CH = CH – OH (e) CH2 = CH – F and CH2 = CH – Br

(e) and Sol.
Sol.
24. In which of the following pairs, indicated

22. Which of the following pairs has less reso- bond is of greater strength :
nance energy :
(a) CH 3 − CH 2 − Br and CH 3 − CH 2 − Cl
↑ ↑
(a) and
(b) CH 3 − CH = CH − Br and CH 3 − CH − CH 3
↑ →|
(b) and
Br
(c) and
(c) and CH 3 − CH 2 − Cl
↑
(d) CH 2 = CH − CH = CH 2 and
(d) and
↑
CH 2 = CH 2 − CH 2 − CH 3
↑
(e) and
Sol. (e) and
Sol.
23. Which of the following pairs has higher

resonance energy :
25. In which of the following pairs, indicated

(a) and bond having less bond dissociation energy :
(a) and CH 2 = CH 2
(b) CH2 = CH – O – CH = CH2 and ↑
CH2 = CH – NH – CH = CH2
(b) CH 3 − C ≡ CH and HC ≡ CH
Θ Θ
(c) CH 2 = CH − N H and HN = CH − N H ↑ ↑
GOC Page # 49
Cl–C6H4+
(c) and
+ +
+
(b)
Sol.
(d) and
(e) and
(f) and
28. Explain why each compound is aromatic,
antiaromatic or nonaromatic.
Sol.
(a) N (b) N S
O
isoxazole 1,3-thiazole
26. Compare the C–N bond-length in the follow-
ing species: H
+
(c) (d)
O O
(i) (ii)
pyran pyrylium ion
(iii) (e) (f)

O N
H
Sol. γ-pyrone 1,2-dihydropyridine
NH2
27. Rank the following sets of intermediates in N

(g)
increasing order of their stability given ap- N O
propriate reasons for your choice
H
(a) C6H5+, p–NO2(C6H4)+, p–CH3–(C6H4)+, p–
cytosine
Page # 50 GOC
Sol.
O OH
31. Square acid is a diprotic acid

O OH
with both protons being more acidic than acetic

acid. In the di-anionafterthe loss of both
protons all of the C-C bonds are the same
length as well as all of the C-O bonds. Provide
a explanaton for these observations.
Sol.
29. Ordinarily the barrier to rotation about a carbon-

carbon double bond is quite high but compound
A have a rotational barrier of only about 20 K
cal / mol
nC3H7
nC3H7
What is the reason for this ?

Sol. 32. Match each alkene with the appropriate heat
of combustion:
Heats of combustion (kJ/mol) : 5293 ; 4658;
4650; 4638; 4632
(a) 1-Heptene
(b) 2,4-Dimethyl-1-pentene
(c) 2,4-Dimethyl-2-pentene
(d) 4,4-Dimethyl-2-pentene
30. Which is more acidic and why ? (e) 2,4,4-Trimethyl-2-pentene
Sol.
(A) (B)
Sol.
33. Choose the more stable alkene in each of the

following pairs. Explain your reasoning.
(a) 1-Methylcyclohexene or 3-methylcyclohexene
(b) Isopropenylcyclopentane or allylcyclopentane
GOC Page # 51
(c) or
(i)
Sol.
(ii)
34. Consider the given reaction:
Pd / C
+ 3H2 →
In the above reaction which one of the given

ring will undergo reduction?
Sol.
(b) and
35. Compare heat of hydrogenation (Decreasing

order)
(a) heat of hydrogenation
Page # 52 GOC
(c) and (iii)
(iv)
(d) and
(B) (i)
(e) CH2 = CH – CH and

(ii)
CH2 = C
(iii)
37. Among the following pairs identify the one

36. (I) Stabi l i ty ord er and (II) he at of which gives higher heat of hydrogenation :
hydrogenation orders.
(a) and
(A) (i) (ii)
GOC Page # 53
39. Write stability order of following intermediates:

⊕ ⊕
(i) (a) CH 3 − CH 2 (b) CH 3 − CH − CH 3
(b) and
CH 3
|
(c) CH 3 − C ⊕
|
CH 3
(c) CH3 – CH = CH – CH3 and
CH3 – CH2 – CH = CH2
⊕
⊕
(ii) (a) (b)
(d) and
⊕
(c)
38. Discuss the following observations:

(a) C–Cl bond in vinyl chloride is stronger than in
chloroethane.
(b) Carbon-carbon bond length in ethene is shorter ⊕
than in CH2 = CHOCH3 (iii) (a) (b) ⊕
(c) CH3SH is stronger acid than CH3OH
(d) CH3CH2NH2 is stronger base than CH2 = CHNH2.
Sol. (c)
⊕
•
(iv) (a) CH3 − CH2
CH3
• |
(b) CH3 − CH− CH3 (c) CH3 − C •
|
CH3
Page # 54 GOC
(v) ( a ) (b) (c)
(vi) (a) (b) (c)
CH3
Θ Θ |
(vii) (a) HC ≡ C (b) CH3 − CH− CH3 (c) CH3 − C Θ
|
CH3
(viii) (a) (b) (c)
(ix) (a) (b) (c)
(x) (a) (b) (c) (d)
Θ Θ
(xi) (a) HC ≡ C (b) CH2 = CH (c) CH3 − CH2
GOC Page # 55
•
(xii) ( a ) H C ≡ C (b) CH2 = CH CH2⊕ CH2⊕
• OH
(c) CH3 − CH2 (iii) (a) (b)
OH
CH2⊕
40. Write stability order of following intermediates:
(c)
⊕ ⊕
CH2 CH2 OH
(i) (a) (b)
N OMe
O O
CH2
CH2⊕ CH2
(c)
(iv) (a) (b)
F Cl
CH2 CH2 Θ Θ
(v) (a) CH2 − CH (b) CH2 − CH3
||
(ii) (a) (b) O
Cl N
O O
CH2 O O O
CH2 (vi) (a) (b)
(c) (d)
(c)
CN
º
Page # 56 GOC
CH2 CH2–CH2
(vii) (a) (b)

⊕ ⊕
CH2 CH2
(xii) (a) (b) H

(c) C H
H
H C H
H
⊕
CH2
H
(c) C H
(viii) (a) (b) H
(c)
CH⊕2 CH⊕2
(xiii) (a) (b)
(ix) (a) (b)

CH3 CH2Me
CH2⊕ CH2⊕
(c) (d)
(x) (a) (b) CH Me2 CMe3
(c) (d)
41. Write increasing order of heat of hydrogenation :
(i) (a) (b)
(xi) (a) (b)

(ii) (a) (b)
(c) (d)
(c)
GOC Page # 57
(iii) (a) (b) 42. Give decreasing order of heat of combustion

(HOC):
(c) (d)
(i) (a) (b)
(e)
(c)
(iv) (a) (b)
(c)
(ii) (a) (b)
(c) (d)
(v) (a) (b)
(c) (HOH per π bond)

(iii) (a) (b)
(vi) (a) (b)
(iv) (a) (b)
(c) (HOH per benzene ring)

(c)
(vii) (a) (b)
43. Arrange in order of C–H bond energy

a
H-CH2
d
H-CH-CH-C-CH3
c b
H e H H
(viii) (a) (b)
CH2
f
H
Page # 58 GOC
Sol. 46. (A) Which compound has the greater electron
density on its nitrogen atom ?
N or N
H H
44. H o w m a n
2 released when 46 gm of
y g r a m s o f H
sodium is treated with excess of ethyl alcohol. (B) Which coompound has the greater electton
Sol. density on its oxygen atom ?
O O
NHCCH 3 or NHCCH 3
Sol.
45. Use the following data to answer the questions
below:
H2
Ni
∆H = – 28.6 Kcal mol–1
excess H2
(Ni)
∆H = – 116.2 Kcal mol–1
Anthracene
Calculate the resonance energy of anthracene
in kcal/mol.
Sol.
GOC Page # 59
Exercise - III
1. Match the column:
Column I Column II
(A) (P) Six π electrons
(B) (Q) Four π electrons
NH
(C) (R) Aromatic Compounds
N
H
H– N
(D) (S) Anti-aromatic compound
Sol.

Column I Column II
(A) (P) Hybrid state of each atom sp2
(B) (Q) Anti aromatic
(C) (R) Delocalisation of π bond
(D) (S) None aromatic
Sol.
(T) Obeys Huckel's Rule for aromatically

Column I Column II
(A) NH (P) Non aromatic
Page # 60 GOC
(B) (Q) Anti aromatic
(C) (R) Resonance

O
(D) (S) Aromatic
Sol.

Column I Column II
+ +
(A) CH3OCH2 or CH2NHCH2 (P) First is more stable than second
+ +
(B) CH3OCH2CH2 or CH3OCH2 (Q) Second is more stable than first
(C) + or + (R) Not resonating structure of each other
+ +
CHCH3 CHCH3
(D) or (S) Resonance is present in both carbocation
Sol.
GOC Page # 61
Exercise - IV(A)
Single choice questions:
1. Thebond betweencarbon atom (1) and carbon atom 7. Choose the correct statement from the ones given
(2) in compound below for anilinium ion
N ≡ C – CH = CH2
NH3 NH3
1 2 3
Involves the hybridisation as (I) (II)
(A) sp2 and sp2 (B) sp3 and sp
(C) sp and sp2 (D) sp and sp
(A) II is not an acceptable canonical structure because
2. Polarisation of electrons in acrolein may be written as carbonium ions are less stable than ammonium ions.
(B) II is not an acceptable canonical structure because
(A) CH2 = CH – C = O (B) CH2 = CH – CH = O
it is non aromatic
(C) CH2 – CH – CH = O (D) CH 2 = CH – CH = O (C) II is not an acceptable canonical structure because

the nitrogen has 10 valence electrons.
3. The compound in which C uses its sp3 hybrid orbitals
forbond formation is (D) II is an acceptable canonical structure
(A) HCOOH (B) (H2N)2CO 8. Most stable carbonium ion is

(C) (CH3)3CHO (D) CH3CHO (A) p-NO2 – C6H4 –+CH2 (B) C6H4 –+CH2
Sol. (C) p-Cl – C6H4 –+CH2 (D) p-CH3O – C6H4 –+CH2
9. In the following compounds
OH
OH
(I) (II)
4. The number of sigma and π-bonds in 1-butene 3-yne
are
CH3
(A) 5 σ and 5 π (B) 7 σ and 3 π OH
(C) 8 σ and 2 π (D) 6 σ and 4 π OH
Sol.
(III) (IV)
NO2
NO2
The order of acidict is
5. The hybridisation of carbon atoms in C -C single bond
(A) III > IV > I > II (B) I > IV > III > II
of H – C ≡ C – CH = CH2 is
(C) II > I > III > IV (D) IV > III > I > II
(A) sp3 – sp3 (B) sp2 – sp3
(C) sp – sp2 (D) sp3 – sp
10. In the following compounds, the order of basicity is
6. Which is the decreasing order of strenght of the bases
OH–, NH2–, H – C = C– and CH3 – CH2–
(A) CH3 – CH2– > NH2– > H – C ≡ C– > OH–
(B) H – C ≡ C– > CH3 – CH2– > NH2– > OH– (I) (II)
N N
(C) OH > NH2 > H – C ≡ C > CH3 – CH2
– – – –
(D) NH2– > H – C ≡ C– > OH– > CH3 – CH2– |

H
Page # 62 GOC
14. Amongst the following, the most basic compound is

O
(A) C6H5NH2 (B) p-NO2 – C6H4NH2
(III) (IV) (C) m-NO2 – C6H4NH2 (D) C6H4CH2NH2
N N
| | 15. THe correct order of basicities of the following com-
H H pounds is
(A) IV > I > III > II (B) III > I > IV > II NH2
(C) II > I > IIII > IV (D) I > III > II > IV (i) CH3 – C (ii) CH3 CH2NH2
NH2
Sol.
O
||
(iii) (CH3)2NH (iv) CH3 CNH2
11. Among the following compounds, the strongest acid (A) ii > i > iii > iv (B) i > iii > ii >iv
is (C) iii > i > ii > iv (D) i > ii > iii > iv
(A) HC = CH (B) C6H6 Sol.
(C) C2H6 (D) CH3OH
Sol.
16. Which of the following hydrocarbons has the lowest

dipole moment?
12. The most unlikely representation of resonance struc- (A) cis-2-butene (B) 2-butyne
ture of p-nitrophenoxide ion is (C) 1-butyne (D) H2C = CH – C ≡ CH
Sol.
O–N=O O–N–O
(A) (B) 17. Which of the following acids has the smallest disso-
ciation constant ?
O O
(A) CH3CHFCOOH (B) FCH2CH2COOH
(C) BrCH2CH2COOH (D) CH3CHBrCOOH
O=N=O O–N=O Sol.
(C) (D)
18. Which ofthe following represent the given mode of
O O
hybridisation sp2 – sp2 – sp – sp from left to right ?
13. Which of the following hasthe most acidic hydrogen : (A) CH2 = CH – C ≡ CH (B) HC ≡ C – C ≡ CH
CH2
(A) 3-hexanone (B) 2,4-hexanedione (C) H2C = C = C = CH2 (D)
(C) 2,5-hexanedione (D) 2, 3-hexanedione H 2C
Sol.
19. Maximum dipolemoment will be of
(A) CCl4 (B) CHCl3
(C) CH2Cl2 (D) CH3Cl
GOC Page # 63
Sol.
OC OH
HO
NO2
(D)
OH OH ..
CO
C
O
NO2 Sol.
20. 2 mole of NaNH2
CH
H3N
OH z NH3
y
21.
Product (A). The product A will be COOH

x
Correct order of acidic strength is
C OH
OO (A) x > y > z (B) z > y > x
(C) y > z > x (D) x > z > y
NO2 SO3H
(A)
CH3COONa (excess)
CH 22. (aq. solution)
O Me
C O
OO
(B) SO3COOCH3
..
C
(A) (B)
OH
Me
OC O
HO SO3Na COONa
NO2 (C) (D) + H2SO3

(C) Me Me
CH
23. For 1-methoxy-1,3-butadiene, which of the following
O
resonating structure is the least stable ?
Page # 64 GOC
(A) H 2C – CH – CH = CH – O – CH 3
O
N
(B) H 2C – CH = CH – CH = O – CH 3 (C)
O
(C) H 2C = CH = CH – CH – O – CH 3
(D) H C = CH – CH – CH = O – CH O
2 3
N
Sol. (D)
O
27. Statement-1: p-Hydroxybenzoic acid has a lower boil-

ing point then o-hydroxybenzoic acid.
24. When benzene sulfonic acid and p-nitrophenol are
treated with NaHCO3, the gases released respectively Statement-2: o-Hydroxybenzoic acid has a
are intramoleculer hydrogen bonding.
(A) SO2, NO2 (B) SO2,NO
(C) SO2,CO2 (D) CO2,CO2
Sol.
(A) Statement-1 is true, statement-2 is true and state-

ment-2 is correct explanation for statement-1.
25. (I) 1, 2-dihydroxy beznene (B) Statement-1 is true, statement-2 is true and state-
(II) 1, 3-dihydroxy benzene ment-2 is NOT correct explanation for statement-1.
(III) 1, 4-dihydroxy benzene (C) Statement1 is true, statement-2 is false.
(IV) Hydroxy benzene
(D) Statement1 is false, statement-2 is true.
The increasing order of boiling points of above men-
28. Hyperconjugation involves overlap of the following or-
tioned alcohols is
bitals
(A) I < II < III < IV (B) I < II < IV < III
(A) σ – σ (B) σ – p
(C) IV < I < II < III (D) IV < II < I < III
(C) p – p (D) π – π
Sol.
29. The correct stability order for the following species is
(I) (II)
O
26. Among the following, the least stable resonance
structur is
(III) (IV)
O
O
(A) N (A) II > IV > I > III (B) I > II > III > IV
(C) II > I > IV > III (D) I > III > II > IV
O
30. The correct acidity order of the following is
OH OH
O
(B) N
(I) (II)
O
Cl
GOC Page # 65
COOH 35. The molecule(s) that will have dipole moment is/are
COOH
(A) 2, 2 dimethyl propane (B) trans 2-pentene
(III) (IV) (C) cis 3-hexene

(D) 2, 2, 3, 3-tetramethyl butane
CH3
Sol.
(A) III > IV > II > I (B) IV > III > I > II
(C) III > II > I > IV (D) II > III > IV > I
31. The correct stability order of the following resonance 36. An aromatic molecule will:
structures is
(A) have 4n π electrons
+ –
(I) H C = N (II) H C+ – (B) have (4n +2) π electrons
2 =N 2 –N=N
– + – + (C) be planar (D) be cyclic
(III) H 2C –N=N (IV) H 2C –N=N
Subjective
(A) I > II > IV > III (B) I > III > II > IV
(C) II > I > III > IV (D) III > I > IV > II 37. The total number of basic group in the following form
of lysine is
32. In the following carbocation; H/CH3 that is most likely
to migrate to the positively charged carbon is
O
+
H H NH3 – CH2 – CH2 – CH2 – CH2 – CH – C
–
1 2 + 4 5 O
H3C – C – C – C –CH3 NH2
3
OH H CH3 Sol.
(A) CH3 at C-4 (B) H at C-4

(C) CH3 at C-2 (D) H at C-2
33. Among the following compounds, the most acidic is:
(A) p-nitrophenol 38. The total number of contrubting structure showing
(B) p-hydroxybenzoic acid hyperconjugation (involving C-H bonds) for the follow-
(C) o-hydroxybenzoic acid ing carbocation is
(D) p-toluic acid
CH3 CH2CH3
Sol.
Multiple Choice Questions:

34. Phenol is less acidic than
(A) acetic acid (B) p-methoxy phenol
(C) p-nitrophenol (D) ethanol
Sol.
Page # 66 GOC
Exercise - IV(B)
1. Among the given catins, .................is most stable.

(sec-butyl carbonium ion, tert-butyl carbonium ion,
n-butyl carbonium ion) 13. Out of anhydrous AlCl3 and hydrous AlCl3 which is
more soluble in diethyleither ? Explain with reason.
2
2. T h e c o m p o u n d h a v in ghybridised
b o t h s p a n d s p
carbon atom is ......... (propene, propane, Sol.

propadiene)
3. In acidic medium, ......... behaves as the strongest
base. (nitrobenzene, aniline, phenol)
4. ......... ring is most strained. (cyclopropane,
cyclobutane, cyclopentane)
5. The terminal carbon atom in butane is .......... 14. Match Ka values with suitable acid:
hybridised. Ka Acid
6. A ............. diol has two hydroxyl groups on
.............. carbon atoms. (i) 3.3 × 10–5 (A) COOH
7. Arrange the following in the orer of their increasing

basicity.
(ii) 4.2 × 10–5 (B) Me COOH
p-toluidine, N, N-dimethyl-p-toluidine, p-nitroaniline,
aniline.
(iii) 6.3 × 10–5 (C) Cl COOH
8. The shape of ( C H3) is ...............
9. The bond dissociation energy needed to form the
benzyl radical from toluene is ............. than the (iv) 6.4 × 10–5 (D) MeO COOH
formation of th methyl radical from methane.
10. The kind of delocalisation involving sigma bond
orbitals is called ................. (v) 30.6 × 10–5 (E) O2N COOH
11. Give reasons for the following in one or two sen- Sol.
tences. The central carbon-carbon bond in 1, 3-
butadiene is shorter than that of n-butane.
Sol.
12. Give reasons for the following CH2 = CH– is more

basic than HC ≡ C–.
Sol.
GOC Page # 67
15. Give resonating structures of following compound:
OH
Sol.
16. Which of the following is more acidic and why ?
NH3 NH3 F
Sol.
17. Predict whether the following molecules are iso struc-

tural or not. Justify your answer.
(i) NMe(3 (ii) N(SiMe3)3
Sol.
GOC Page # 68
Answers
Exercise-I
1. A 2. C 3. B 4. C 5. D 6. C 7. B
8. D 9. B 10. C 11. D 12. A 13. C 14. C
15. D 16. A 17. C 18. B 19. C 20. B 21. C
22. D 23. B 24. B 25. D 26. C 27. A 28. C
29. B 30. B 31. C 32. D 33. B 34. A 35. A
36. C 37. A 38. D 39. C 40. B 41. C 42. C
43. A 44. B 45. B 46. B 47. A 48. A 49. C
50. B 51. A 52. C 53. B 54. C 55. C 56. C
57. A 58. A 59. D 60. A 61. A 62. C 63. B
64. A 65. D 66. D 67. B 68. D 69. B 70. C
71. B 72. C 73. D 74. A 75. C 76. B 77. B
78. B 79. D 80. C 81. A 82. A 83. B 84. A
85. B 86. A 87. B 88. D 89. C 90. B,D
91. a,b,c,d,f 92. c,f 93. b,d,e 94. b,d,e 95. A,B,D 96. A,B,C
Sol.56 Formation of (i) Aromatic, (ii) Antiaromatic
Sol.57 1-bromotripycohe is 1023 times less reactive than Ph3C–Br which is 1011 times less reactive than
tropolium bromide+
Sol.58 Reactivity of R–X incrases with decrease in BD. E. of RX & increase in stability of carbocation
formed.
N N N H
Sol.59 (A) (B) N H (C) (D) N H
N N H
(8 πe–) (8 πe–) (8 πe–) (6 πe–)
Page # 69 GOC
Sol.60 (I) Two benzenoid RS & Two α H
(II) Two benzenoid RS & But zero α H
(III) Only one benzenoid RS zero α H
Sol.61 (A) + M of – OMe is stablising carbocation.
Me CH2 Me – O =CH2
Sol.62 < Me – O – CH2
+I (6 electron) (8 electron)
Resonance Stabilized.
H H
KH
Sol.96 (A) + H2 6 πe– aromatic
O OH
(B) H–Br 6 πe– aromatic
HI
(C) 6 πe– aromatic
O O H
(D) H Br 4 πe– aromatic
GOC Page # 70
Exercise-II
1. B, E, I 2. B, D
3. a = Resonance form, b = A, c = C, d = A & B, e = B & C, f = 0, g = B, h = B
4. (a) is resonance form; (b) is not resonance form due to different number of .p. and b. p.
(c) is not resoanance form due to different no. of .p. and b.p.
5. (A) sp2, (B) sp2, (C) sp2, (D) sp2
6. HC ≡ C – C ≡ CH in it all carbon are sp hybridized C – C σ-bond is shorter than both CH3CH3 & CH2=CH –
CH = CH
7. (a) I, (b) I, (c) II, (d) II
O— O—
8. (a) CH3 C CH2 (b) H C CH CH CH2
CH2 CH2 CH2 CH2 CH2
(c)
—
(d) (e) O O O O
(f) NH (g) (h)

O
O
(i) CH3— C H—CH=CH—CH=CH—CH3 (j) CH3— CH—CH=CH—CH=CH2
O
(k) H2 C – CH = CH – CH = CH2 (l) (m) Me–CH= Cl
Page # 71 GOC
O
O
9. (A) (Me)2C=NH2 (Me)2C NH2 (B)
NH NH
O O O
12. (a) II, (b) II, (c) II, CH3 – C – CH – CH = C – CH3 (d) II, CH3–CH=CH – CH = N
O
NH2
(e) II, CH3 – CH2 – C – NH2
13. (a) ii, (b) ii, (c) ii, (d) i, (e) i
14. (a) I, (b) I, (c) I, (d) II, (e) II
15. (a) I, (b) II, (c) II, (d) II, (e) I
16. (a), (c), (d), (g), (j), (l), (m)
17. (a), (b)
18. (a), (b), (c), (f)
19. (a) II, (b) I, (c) I, (d) I, (e) I
20. (a) II, (b) I, (c) I, (d) II
21. (a) II, (b) I, (c) II, (d) II, (e) II
22. (a) II, (b) II, (c) II, (d) II
23. (a) I, (b) II, (c) II, (d) I (e) I
24. (a) II, (b) I, (c) I, (d) I, (e) II
25. (a) I, (b) I, (c) II (d) II (e) I (f) II
26. iii > ii > i
27. (a) ii < Iv < i < iii (b) iii < ii < i
28. (a) A, (b) A, (c) N. A. (d) A, (e) A, (f) N.A. (g) A
GOC Page # 72
nC3H7
29.
nC3H7
One of the R. S. is having both ring aromatic.
30. A>B
O OH O O— O O—
+ +
–H –H
31. H
—
O OH O O O O
R-stablized & intra H-bonding 4 Eq. R.S.
32. (a) 4658, (b) 4638, (c) 4632, (d) 4656 (e) 5293
33. (a) i, (b) i, (c) ii
34. A
35. (a) (i) D > C > B > A (ii) E > C > D > B > A (b) 2 > 1 (c) 2 < 1 (d) 1 < 2 (e) 1 > 2
36. (A) (I) iv > iii > ii > i, (II) i > ii > iii > iv
(B) (I) iii > ii > i (II) i > ii > iii
37. (a) I, (b) I, (c) II, (d) I
38. (a) Due to resonance H2C CH Cl CH2 CH Cl+
(b) In CH2=CH–OCH3, there is single bond character due to resonance
H2C CH OCH3 CH2 CH O+ CH3
(c) Conjugate base of CH3SH ie, CH3 S is more stable than conjugate base of CH3OH, ie CH3O–
+
(d) In CH2=CH–NH2 lone pair of N is delocalized H2C CH NH2 CH2 CH NH2
39. (i) c > b > a (ii) c > b > a (iii) b > c > a (iv) c > b > a
(v) c > b > a (vi) b > c > a (vii) a > b > c (viii) a > b > c
Page # 73 GOC
(ix) a > c > b (x) d > c > b > a (xi) a > b > c (xii) c > b > a
40. (i) b > c > a (ii) b > c > a > d (iii) c > a > b (iv) a < b
(v) a > b (vi) a > b > c (vii) a > b > c (viii) a > b > c
(ix) a > b (x) c > b > a > d (xi) a > c > b (xii) c > a > b
(xiii) a > b > c > d
41. (i) b > a (ii) a > b > d > c (iii) a > b > c > d > e (iv) b > c > a
(v) a > b > c (vi) a > b > c (vii) b > a (viii) b > a
42. (i) c > b > a (ii) a > b > c > d (iii) a > b (iv) c > b > a
43. d<f<b<c<a<e
On the basis of stability of free radical formed after removal of H .
44. 2 C2H5OH + 2Na (46g) → 2 C2H5ONa + H2
46 ⇒ 2 mole Na 1 mole H2 generate

23
It means 2g H2 gas
45. Anthracene is 14 π e's system
i.e. there are 7 π bonds
Expected (theoretical) heat of hydrogen = – 28.6×7 = – 200.2 kcal/mol
Observed (experimental) heat of hydrogen = –116.2
∴ R. E. = – 166.2 – (–200.2)
= 84 kcal/mol
46. (A) Second ; (B) First
GOC Page # 74
Exercise-III
1. (A) P, R; (B) Q, S; (c) P, R; (D) P, R 2. (A) P, R, T; (B) P, R (C) S ; (D) P, Q, R
3. (A) P, R; (B) P, R; (C) R, S; (D) P, R 4. (A) Q, R, S; (B) Q, R; (C) P, R; (D) P, R
Exercise-IV(A)
1. C 2. D 3. C 4. B 5. C 6. A 7. C
8. D 9. D 10. D 11. D 12. C 13. B 14. D
15. B 16. B 17. C 18. A 19. D 20. A 21. D
22. C 23. C 24. D 25. C 26. A 27. D 28. B
29. D 30. A 31. B 32. D 33. C 34. AC 35. BC
36. BCD 37. 2 38. 6
Exercise-IV(B)
1. tert-butyl carbonium ion 2. propadiene 3. aniline
4. cyclopropane 5. sp3
6. gem, same or vicinal, adjacent
7. p-Nitro aniline < Aniline < p-Toluidine < N, N-dimethyl-p-toluidine
Page # 75 GOC
8. Trigonal planar
9. Less
10. Hyperconjugation
11. Delocalisation of π-electron takes place in 1,3-butadiene that's why each carbon-carbon ond acuires
the character of partical double bond. Whereas in n-butane resonance is absent that's why the bond
between carbon is pure single bond.
12. CH ≡ CH is more acidic than CH2 = CH2 so that conjugate base of CH ≡ CH is less basic than CH2 = CH2.
13. Anhydroush AlCl3 is more soluble in diethyl ether
Cl
Et Et
O Al O AlCl3
Et Cl Cl Et
Lewis Lewis Adduct
Base Acid
(anhydrous
AlCl3)
Cl
H H
O + Al O AlCl3
H Cl Cl H
Hygrous AlCl3
(Octet complete)
14. (i) d (ii) b (iii) a (iv) c (v) e
Page # 76 GOC
15.
OH OH OH
NH3
NH3
16. is more acidi than due to –I effect of fluorine.
SiMe3
N N
17. Me Me SiMe3 SiMe3
Me
(Pyramidical)
Given componds are not isostrucutral
Delocalised of l.p. of nitrogen in vacant d-orbital of sillcon makes compound planar.

Exercise - I: (Only One Option Is Correct)

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Exercise - I: (Only One Option Is Correct)

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GOC Page # 27

Exercise - I (Only one option is correct)

1. Bond formation is: 4. In which of the following molecules – NO2 group is

(C) sp2-sp overlap (D) sp2-sp2 overlap Sol.

(A) I > II > III (B) III > I > II

11. (I) CH2 = CH – CH = CH – OCH3

8. (I) CH2 = CH – CH = CH2 (II) CH2 – CH = CH – CH = OCH3

(II) CH2 – CH = CH – CH2 (III) CH2 = CH – CH – CH – OCH3

(II) CH2 – CH = CH – CH2 (IV) CH2 = CH – CH – CH – OCH3

(A) (B) Sol.

(C) (D) All haveequal stability

Among these canonical structures of pyridiine, the

(I) (II) (III)

In phenol, π-electron-density is maximum on 4

(C) meta and pera positions (D) none of these

25. In which of the following pairs, first species is

Among these compounds, the correct order of 29. 3 3 3

(III) CH3 – CH – CH3 (IV) C6H5 – CH – CH3

(V) CH3CH CHCH2 CH2

(A) I > II > IV > VI > III > V (A) (B)

NH2 34. In which of the following molecules resonance

(C) C2H4 > C2H6 > C2H2 > C6H6

38. Which of the following compouds is not aromatic

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

41. Which of the following statements would be true

The most stable canonical structure of this mol- 1 3

N=N (C) Cl – N and C3 – N bonds are of same length

40. 42. Ease of ionization to produce carbocation and bro-

mum in whichof the following compounds ?

(C) mixture of (A) & (B) (D) none of these

43. Ease of ionization to produce carbocation and bro- Sol.

46. (I) (II) (III)

The barrier for rotation about the indicated bonds

47. (I) (II) (III)

48. Find out the hybridisation state of carbon atoms

(D) sp3 sp sp sp2 sp sp2 sp sp sp3

50. Writecorrect order of stability of following

51. The abstraction of proton will be fastest, in which

52. Number of π-electron in (C4H4)2– is

(III) CMe2 (A) 2 (B) 4

(C) (D) 56. Which one of the following statements is True:

(A) PhLi adds to both compound with equal ease

57. Correct order of rate of hydrolysis or rate of re-

(I) (II) (III)

60. Arrange the following carbocations in the increas-

(A) I > II > III (B) I > II = III

58. Write correct order of reactivity of following halo-

(C) V > I > IV > III > II

62. Statement-1: Me – CH is more stable than MeO

59. Which of the following heterocyclic compounds – CH2

66. Which of the following is the strongest base

63. When – CH3, CH3 – CH – and CH3 – C – groups NH2 NHCH3

are introduced on benzene ring then correct or-

(A) CH3 – > CH3 – CH – > CH3 – C – Sol.

(C) CH3 – CH – > CH3 > CH3 – C –

(A) NH3 < CH3NH2 < (CH3)2NH

70. Which one of the following is the strongest base

(I) CH3CH2 (II)

74. Rank thefollowing radicals in order of decreasing

80. (I) (II) (III) 82. Cl

Which of the following choice is the correct (A) ClO4 (B) Ag

83. Which can lose a proton more readily, a methyl

(I) CH3 (II) CH3