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Question Bank
Target IIT JEE-2020
Rank Boosting Course (RBC)

GOC
1. Determine the inductive effect of phenyl ring on attached group in the (a) and (b) molecules respectively
O

(a) (b)
(a) a : + I, b : + I (b) a : – I , b : + I (c) a : + I , b : – I (d) a : – I , b : – I

2. Which is the least stable resonating structure of the given molecule?

O

O O O O

(a) (b) (c)  (d)
 

3. Identify the resonance hybrid of the given ion :

O
S O
O
O
–1/4 –1/2 –3/4 –1
O O O O
–1/4 –1/2 –3/4 –1
(a) –1/4 S O (b) –1/2 S O (c) –3/4 S O (d) –1 O S O
O O O
–1/2
O–1/4 O O–3/4 –1
O

4. Which of the following is the most stable?

(a) (b) (c) (d)

5. Which of the following has minimum heat of hydrogenation?

(a) (b) (c) (d)

6. The decreasing order of bond dissociation energies amongst the C–H bonds labelled x, y, z (in homolysis)
is:
H H
z x

y
H

(a) x > y > z (b) x > z > y (c) z > x > y (d) y > z > x
7. Determine the stability order of given intermediates.
Me OMe Me
 OMe H2C  OMe

 H2C — OMe
Me (IV)
(I) (II) (III)

(a) I > II > III > IV (b) I > II > IV > III (c) IV > I > II > III (d) III > I > II > IV
8. Rank the following reactions in DECREASING order of heat of hydrogenation.
2H2 2H2
(a) (b)

2H2
(c)
(a) a>c>b (b) c>a>b (c) a>b>c (d) b>c>a

9 Which of the following bonds is the longest ?

O
(a) (b) (c) (d)
NH2 NH2 CH2 = NH NH2
(a) a (b) b (c) c (d) d

10. What is the correct order of stability among the given carbocations?
CH2
CH2

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

(a) II > I > IV > III (b) II > I > III > IV (c) I > II > IV > III (d) I > II > III > IV

11. Which of the following are not resonating structures of each other?
(a) CH3 – N = C = S & CH3 – S – C  N
 
(b) CH 3  C  O & CH 3  C  O
O O
(c) CH3–C–OH & CH 3–C=O–H
(d) CH2 = CH – C  N & CH2–CH=C=N

12. Find correct order of resonance energy for

(I) OCH3 (II) (III) OCH 3
OCH 3
(a) III > I > II (b) II > I > III (c) I > II > III (d) III > II > I

13. Which of the following substituents will decrease the acidic strength of phenol?
(a) – NO2 (b) – CN (c) – CH3 (d) – CHO
14. Correct order of stability of carbocations:

CH 3 CH 3
| |
(i) CH 3  CH 2  CH 2 (ii) CH 3  CH  CH 2 CH
(iii) 3  C  CH 2
|
CH 3

(a) (iii) > (ii) > (i) (b) (ii) > (iii) > (i) (c) (i) > (iii) > (ii) (d) (i) > (ii) > (iii)

15. Which of the following is an aromatic specie?

O
(a) (b) (c) (d)

16. Which is not a valid resonating structure of H2C = CH – CH = CH – O – CH3 ?

(a) H2C–CH=CH–CH=O–CH3 (b) H2C=CH–O=CH–CH–CH3
(c) H2C=CH–CH–CH=O–CH3 (d) H3C–O–CH–CH=CH–CH2

17. What is C – O bond order for H 3C–CH 2–C–O ?

O
(a) 2 (b) 1.5 (c) 0.5 (d) 1

18. Solubility order in H2O for the following compounds is :

(I) H2C – CH – CH – CH2 (II) H3C – CH2 – CH2 – CH2
OH OH OH OH OH
(III) H3C – CH2 – CH2 – CH3
(a) I > III > II (b) I > II > III (c) II > III > I (d) III > II > I

19. Which of the following alkene has minimum heat of hydrogenation.

(a) (b) (c) (d)

20. Which is more stable?

 
(I) CH 3  C  CH 3 (II) CD3  C  CD3
| |
CH 3 CD3
(a) I > II (b) II > I (c) I = II (d) Stability can't be predicted
21. Which of the isomer of C4H8 is most stable?

(a) (b) (c) (d)

22. Which one of the following will have the longest C=C bond length?

(a) (b) (c) (d)

23. In which of the following, the 2nd structure has more resonance energy.

(a) vs (b) vs
O N
H CH3

(c) CH2=CH–CH=CH– CH2 vs (d) All

24. Which compound has identical C–C bond length?

(a) (b) (c) (d)

O

25. Which compound is most basic among the following?

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

(a) I (b) II (c) III (d) IV

26. What is bond length order ?

a b
c
d
(a) d > b > a = c (b) d > a = b = c (c) b = d > a = c (d) d < a = b = c

27. Increasing order of stability of following resonating structures is :

 
N  N  N
C C C
(I) O (II) O (III)
O
(a) I < II < III (b) III < II < I (c) II < III < I (d) II < I < III

28. Which group has greater +M effect than —N ?

(a) –NH2 (b) –NH–C–Me (c)  O (d) –OH

O
29. Which of the following will have lowest dissociation constant (Ka) ?
NO2
COOH COOH
(a) (b)

Cl
COOH COOH
(c) (d)

30. Select the one which is most basic among the following:

Me
(a) N–H (b) N (c) O N–H (d) O
Me

31. Which of the following pair having same functional group?

(a) CH3–CH2 – NH2 , CH3 – CH – NH2

CH3
OH OH

(b)
,

(c) CH3 – C – O – CH3 , CH3 – C – CH2 – CH2– O – CH3

O O
(d) CH3 – CH2 – C – H , CH3 – C – CH3

O O

32. Which of the following is not + I group?

(a) –SiMe3 (b) –CMe3 (c) –COO¯ (d) None of these

33. The correct order of decreasing basicity of the compounds is:

(I) Et  N  Et (II) (III) (IV)

| N
N N
Et H
(a) I > II > III > IV (b) III > I > II > IV (c) I > III > II > IV (d) I > III > IV > II
34. Which compound has lesser C–O bond length in comparison to C–O bond length in
O

O OH O O

(a) (b) (c) (d)

N

H
 OH OH COOH COOH

35. Ka value order for will be

(I) (II) NO2 (IV)
(III)

(a) III > II > IV > I (b) IV > III > II > I
(c) III > IV > II > I (d) III < IV < II < I

36. Which of the following is not aromatic compound /ion?

OH NH2

(a) (b) (c) (d)

O

37. Which of the following reaction is most favourable?


(a) CH3–C CH + NaOH  CH3 – C  C Na + H2O

(b) CH4 + NaOH  CH3Na + H2O
OH 
ONa

(c) + NaHCO3  + H2O + CO2

(d) EtONa + H2O  EtOH + NaOH

38. Arrange the following compounds in order of increasing basic strength.

CH2–NH2
NH2

N N
H (IV)
(III)
(I) (II)
(a) III > II > I > IV (b) III > IV > II > I
(c) IV > III > II > I (d) IV > II > III > I

39. Correct increasing order of (C–C) bond length is

NH2 CH3

(y) (z)
(x)
CHO
CHO CHO
(a) x < z < y (b) y < z < x (c) z < y < x (d) x < y < z

40. Which among following is correct order of –M strength?

O O
|| ||
(a) – CHO < <
 C  OR  C  NH 2
(b) –CN > –CH = NH > –CHO
 (c) –Ph < NO2 < NH2

O O O
|| || ||
(d)  C  NH  C 2 H 5 <  C  OCH 3 < CH

41. 1 mol of which compound can release maximum heat when it reacts with air?
(a) E-cyclo decene (b) Z–cyclo decene
(c) E–cyclo pentadecene (d) Z– cyclo pentadecene
42. Which of the following is a +I group?
O O O O
(a) –C–H (b) –C–Me (c) –C–NH2 (d) –C–O

43. Which of the following statement is correct?

(a) The relative order of + I groups is
–O > NH > –CH2
(b) The relative order of – I groups is
  
– NF3 > – NH 3 >  N Me3 > –NO2
(c) The relative order of basic strength in aqueous solution is
NH3 < MeNH2 < Me2NH < Me3N
(d) None of these

44. Which of the following compound is least basic?

O O O O

(a) N (b) (c) N (d) N

H N
H H
H

45. Which of the following is least stable carbanion?

OCH2 OCH2 OCH2

(a) CH 3  OCH 3 (b) (c) (d)

NO2 CN OCH3

46. Arrange the following in decreasing order of acidic strength.

COOH COOH COOH
COOH

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

NO2 SO3H CH3

(a) I > II > III > IV (b) II > III > IV > I
(c) III > II > I > IV (d) III > I > II > IV
47. Find the number of sp2 hybridised atoms in the following compound.
C N

CH=CH–CH=CH2

(a) 12 (b) 14 (c) 15 (d) 11

48. Which of the following resonating structure is most stable?

 
 
(a) CH  O  CH  CH  CH (b) CH 3  O  CH  CH  CH 2
3  2

    
(c) CH 3  O  CH  CH  CH 2 (d) CH 3  O  CH  CH  CH 2

49. Which of the following can show resonance with the alkene?
O
CN COOH

(a) (b) (c) (d)

50. Which of the following is non-aromatic?

(a) (b) (c) (d)

N

51. In the following compounds:

OH OH OH OH

NO2
(I) (III) NO2
CH3
(II) (IV)

The order of acidity is:

(a) III > IV > I > II (b) I > IV > III > II (c) II > I > III > IV (d) IV > III > I > II

52. Which of the following compound is most basic?

O NH NH O
(a) CH3– C – NH2 (b) H2N– C – NH2 (c) CH3– C – NH2 (d) Ph – C – NH2

53. Select the incorrect statement for

(a) 4 electrons are participating in resonance (b) Compound is anti aromatic
(c) It is a Homocyclic compound (d) Compound is non aromatic
54. Which of the following is most basic?
NH2 NH NH2 NH2
OCH
(a) (b) (c) (d)
NO2
OCH

55. What is correct order for bond length for mentioned bonds?
a
b CH
H—C—O— 3
c

(a) a = b = c (b) c > a > b (c) b > c > a (d) b > a > c

56. Which specie is aromatic?

O
(a) (b) (c) (d)
: :

O N O
O
H

57. Most stable carbocation amongst the following is :

CH
 
CH2
CH 2
CH2 2

(a) (b) (c) (d)

OCH3 NO2
CH3 OCH3

58. Least stable carbanion amongst the following is :

CH2 CH2 CH2 CH2

(a) (b) (c) (d)

CH3 CN
NO2

59. Consider following compounds:

a b c

Which bond is strongest?

(a) a (b) b (c) c (d) Can not be predicted
60. Which compound has highest electron density in benzene ring?
CH3 NO2 OH NH2

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

(a) I (b) III (c) IV (d) II
61. Which of the following is most basic compound ?
(a) H3C – C  N (b) H3C – CH = NH (c) H3C – C = N (d) H2C = C = N
62. Which of the following compound has least value of pKa?

OH HO
(a) (b) (c) (d)
O O O OH O
OH

63. In which pairs, specie-I is more stable than specie-II?

O O
(a) H–C–CH2–O , CH3–C–O
O O O O
(b) CH3–C–CH–CH2–C–CH3, CH3–C–CH–C–CH3
O O
(c) CH3–CH–CH2–C–CH3, CH3–CH2–CH–C–CH3
O
O
(d) N , N

64. Which of the following is least acidic compound ?

COOH OH OH SH

(a) (b) (c) (d)

NO2

CH2

65. Which resonating structure is most stable for ?


N
O O

CH2 CH2 CH2 CH2

(a) (b) (c) (d)

N N N N
O  O   
O O O O O O

66. Which of the following alkene is least stable ?

(a) (b) (c) (d)

67. Heat of combustion is be maximum for

(a) (b) (c) (d)

68. Which of the following has the highest heat of hydrogenation ?

(a) (b) (c) (d)

69. Which of the following carbanion is most stable ?

(a) (b) (c) (d)

O O O
O

70. C 6 H12 1

mole

(A) H2

Which isomer of A has maximum heat of combustion?

(a) (b) (c) (d)

71. Which of the following pairs are resonance structures of each other?
O OH
C
H3C CH3 H3C CH2
(I) (II)

 
(III) (IV)
(a) I, II, III, IV (b) I, IV (c) I, II, III (d) I, III, IV

72. ‘y’ = Number of compound having –I group directly attached to benzene.

SO3H CN COOH NO2

CH3 CF3 OH

Find the value of ‘y’?

(a) 5 (b) 6 (c) 7 (d) 8

73. Which of the following is not an aromatic compound?

O
(a) S
(b) (c) (d)
B
H
74. In which of the following pair Ist compound has more resonance energy than IInd compound?

(a) (b) SH
(I) (II) S
(I) (II)

(c) (d) O
(I) (I) (II)
(II)

75. Correct order of acidic strength among the following compounds is

OH OH OH OH

NO2
NO2
(I) (II) (III) (IV)
(a) I > II > III > IV (b) II > III > IV > I (c) II > III > I > IV (d) III > II > IV > I

76. Correct order of Basic Strength (Kb order) is :

NH2 NH2

NH2 NH CH3 NH H2N NH

1 2 3 4
(a) 4 > 3 > 2 > 1 (b) 1 > 2 > 3 > 4 (c) 4 > 3 > 1 > 2 (d) 1 > 4 > 3 > 2

77. In which of the following molecules, all atoms are coplanar?

CH3 CN
(a) (b) (c) C=C (d)
CH3 CN

H3C CH3 H3C CH2 H2C CH2

78.
CH3 CH3 CH2
(I) (II) (III)
The enthalpy of hydrogenation of these compounds will be in the order as
(a) I > II > III (b) III > II > I (c) II > III > I (d) II > I > III
79. Which among the given resonance structures is the most stable ?

N N N N
C C C C
(a) (b) (c) (d)
O O O O
80. Determine the correct order of acidity of the following compounds.
O
O
HO O

O HO O
O
(i) (ii) (iii)

(a) i > ii > iii (b) ii > iii > i (c) iii > i > ii (d) iii > ii > i

81. Which of the following is most stable resonance structure?

 
(a) CH 2  CH  C OH (b) CH 2  CH  C  OH
| |
CH CH
|| ||
CH  NH 2 CH  NH 2


(c) C H 2  CH  C  OH (d) CH 2  CH  C  OH
| ||
CH CH
|| |
CH  NH 2 CH

||
NH 2

82. Compare rotational energy barrier about indicated C = C between given compounds.
n-C3H7 n-C3H7 CHO n-C3H7
(I) (II) (III)
n-C3H7 n-C3H7 n-C3H7
CHO CHO
(a) I > II > III (b) III > II > I (c) III > I > II (d) I = II = III

83. Which of the following is correct order of – I ?

(a) –F > – NO2 > – CN > Br (b) –NH3 > NO2 > –CN > –C–H
O
(c) –NH3 > –NH2Me > – NHMe2 > – NMe3 (d) –NH2 > – OH > –Cl > –Br

84. Compare bond length of the indicated bond.

NH–Me NH–Me
(i) (ii) (iii) (iv)
CN
(a) (i) > (ii) > (iii) > (iv) (b) (iv) > (iii) > (ii) > (i)
(c) (iv) > (ii) > (iii) > (i) (d) (i) > (iii) > (ii) > (iv)
85. Which amongst the following has the most extensive hydrogen bonding in aqueous medium?
(a) Ethanol (b) Acetaldehyde (c) Acetone (d) Acetic acid

86. Compare acidic strength among the given compounds.

H Cl Cl H
Cl H
H Cl

(I) (II)
COOH COOH
(a) I > II (b) II > I (c) I = II (d) Can not be compared

87. Which of the order is incorrect?

(a) Acidic strength : O – C – C – OH < O – C – C – OH

O O O O
F F

F C –OH
(b) Acidic strength : > C –OH
F F O O



< <

(c) Stability order : N N N
CH3 CH3 CH3

(d) Basic Strength order : Et2NH > Et3N > Et–NH2 > NH3 (In H2O)

88. The correct order of basic strength for the following bases is / are :
(a) CH3 > NH2 > OH > F
NH2 NH2 NH2
CH3
(b)
CH3
CH3

(c) Both are correct

(d) Both are incorrect

89. Which of the following has highest heat of hydrogenation?

(a) (b)

(c) (d)
90. Which of the following is aromatic ?
H H
B B
(a) (b) (c) (d)

91. Which of the following statement is incorrect?

(a) p-nitro phenol is more acidic than p-flouro phenol.
 
(b) – N F3 is stronger – I group than – N H3
(c) Acidity order : o-nitrobenzoic acid > p-nitrobenzoic acid > m-nitrobenzoic acid
O
||
(d) Acidity order : H3C – COOH > H  C  OH

92. Among the following, the least stable canonical structure is :

O O
(a) N (b) N
O O

O O
(c) N (d) N

O O

93. Find the correct acidic strength order :

NH3 (c)

NH3
(a)
N
H (b)
(a) a > b > c (b) c > b > a (c) b > c > a (d) c > a > b

94. The correct order of basic strength of the following compounds is

H2N NH H2N NH
O
O
NH
(1) (2) (3) NH2 (4)
O
OCH3 CN

(a) 1 > 2 > 3 > 4 (b) 2 > 1 >3 > 4 (c) 3 > 4 > 1 > 2 (d) 1 > 3 > 2 > 4
 OH

2 moles
NaNH
95. HOOC SO3H  
2  X

NO2
OH

The product X will be

OH OH

(a) HOOC SO3 (b) OOC SO3

NO2 NO2
O OH

OH O

(c) OOC SO3H (d) OOC SO3

NO2 NO2
O O

96. Identify the compound having highest basic strength.

OCH3 CHO
NH2 CH3
(a) (b) (c) (d)
H2N NH H2N NH
NH NH

NH2 H2N NH
97. Which of the following compounds will have highest thermodynamic acidic strength?
SO3H

(a) (b) p-nitro phenol

(c) p-Sulpho Benzoic acid (d) 2,4-Dinitro phenol

98. Arrange the compounds in decreasing acidic strength order:

O O O
|| || ||
(I) CH 3  C  CH 2  C  CH 3 (II) CH 3  C  CH 3
(III) CHCH (IV) CH3–CHO
(a) I > IV> III > II (b) I > IV > II >III (c) III > I > IV > II (d) II > IV > I > III

99. The correct basic strength order of the following bases is:
O
NH C CH3 C NH CH3
(I) (II)
O
O O
C CH2 NH2 H2N C CH3
(III) (IV)

(a) I > II > IV > III (b) IV > III > II > I
(c) III > II > IV > I (d) III > IV > II > I

100. Which of the following hydrocarbon is most acidic ?

(a) (b) (c) (d)

 ANSWER AND SOLUTION

1. (b)

+I O –I

Sol. –I
+I

(a) (b)

2. (c)
O

Sol. has negative charge on carbon atom which is less stable than negative charge on oxygen

atom in option A, B & D.

3. (b)
Sol. The molecule has four resonating structures and each oxygen atom has negative charge in 2 out of 4
1
resonating structures. Thus each oxygen atom has average of charge.
2
4. (b)
Sol. (b) and (d) have resonance, thus more stable than (a) and (c). (b) is more stable than (d) because of
more hyperconjugation (more –H).
5. (d)
Sol. c has highest HOH because of most -bonds. (d) has least HOH because of more hyperconjugation
(more –H) thus more stable -bond than a and b.

6. (c)
Sol. Free radical formed at y is most stable because of resonance thus it has least bond dissociation energy.
Free radical formed at z is vinyl free radical, thus least stable.

7. (b)
Sol. I, II and IV carbocations are resonance stabilised and can be compared on the basis of degree of
carbocations. In III only the – I effect of O operates thus it is least stable.
8. (d)
Sol. (a) and (c) Dienes are resonance stabilised while (b) is not. (a) is more stable than (c) because of
greater hyperconjugation. Heat of hydrogenation is inversely proportional to stability for isomers.

9 (d)
Sol. (d) has the lowest % double bond character.
10. (c)

 2
vacant sp


Sol. Carbocation stability : > >  >>
(2RS)
(-bond resonance) (5RS) (unstable)
(Dancing resonance)
(Aryl carbocation)

11. (a)
Sol. First pair is not resonating structure because the position of atoms is not same.

12. (c)
Sol. The order of resonance energy is I > II > III greater the resonance, greater will be resonance energy
and thus III has the lowest resonance energy then I(Extended resonance) > II(cross resonance).

13. (c)
Sol. Acidic strength of phenol will decrease when electron releasing group will be substituted.
14. (d)
Sol. Greater the number of hyperconjugation greater will be the stability of carbocation.

15. (a)

Sol. is an aromatic compound since it is cylic planar, conjugated system and follow Huckel’s rule. It
has (4n + 2)  - electron where n = 1

16. (b)
Sol. Structure can not be changed in resonance.
17. (b)
H3C–CH2–C–O CH3–CH2–C=O
Sol.
O O
Number of bonds between atoms 3
Bond order =  = 1.5
Resonating structures 2

18. (b)
Sol. More the hydroxy groups, more is H-bonding with solvent water and thus more is the solubility.
19. (c)
1
Sol. HOHhyd. 
stability
(1) 3  H (2) 6  H (3) 10  H (4) 4  H
HOH (1 > 4 > 2 > 3)
20. (a)
Sol. (I) 9  H (II) 9  D
Bond strength order : C – D > C–H
+H order : C – D < C–H

21. (d)

H
H H H
Sol. H H

6 H 6H

+ +
H H H
H H H

CH2

Hyperconjugation structures of isobutene and trans-2- butene respectively have 1° anion and 2° anion,
1° anion is more stable than 2° anion.

22. (c)

Sol. more -hydrogen, more will be the hyperconjugation, more will be the [C=C] bond length.i.e.
it will have more single bond character

23. (d)
Sol. In (a) N is better donor than O due to lesser electronegativity. In (b) and (c), the second compound is
aromatic.

24. (d)

Sol. Compound has identical C – C bond length as the negative charge participates in resonance
and molecule is aromatic.
25. (b)
Sol. (b) It is most base as the lone pair of N is not delocalised and also the N atom is sp3 hybridised.

26. (a)
Sol. Partial double bond character appears in bond b due to resonance while there will be pure
predomindently double bond character single bond character in d bond.

27. (d)

 
Sol. N  N  N
C C C
(I) O (II) O (III)
O
Octet incomplete Increased polarity
decreases stability Octet complete

28. (c)
Sol.  O has greater (+M) effect due to greater charge density..
29. (c)
COOH
Sol. is weakest acid among given acids & weakest acid will have lowest Ka value.

30. (a)
Sol. (a) is the most basic due to highest electron density availability for donation.

31. (a)
Sol. In structure (a) 1°-amine is present. So both figures are same.

32. (d)
Sol. All the groups show +I effect.

33. (b)
Sol. In (III), lone pair present in sp3 hybridisation 'N' atom so not delocalised.
In (I), bulky group present on sp3 hybridisation 'N' atom.
In (II), lone pair present on sp2 hybridisation 'N' atom.
In (IV), lone pair present in aromatic compound so least basic.

34. (a)
Sol. (a) has shorter C–O bond length due to pure double bond.
35. (c)
Sol. III and IV are carboxylic acids, thus more acidic than I and II.
I and II
III > IV due to –M of –NO2 in III
II > I due to resonance stabilised phenoxide ion.
36. (c)

Sol.  Incomplete cyclic conjugation.

O

37. (d)
Sol. Strong acid + Strong base l weak conjugate acid + weak conjugate base. For forward direction
reaction conjugate acid-base should be weaker be than acid- base on left hand side.

(a) CH3–C CH + NaOH CH3 – C  C Na + H2O
Acid Base Conjugate base Conjugate acid

Acidic strength CH3 – C  CH < H2O


Basic strength : NaOH < CH3 C C Na
Spontaneous in backward direction
(b) Acidic strength CH4 < H2O in (Reaction backward direction)
(c) Acidic strength Ph–OH < H2CO3 (Reaction in backward direction)
(d) Acidic strength H2O > EtOH (Reaction in forward direction)

38. (d)

Sol. (I) N Lone pair is in resonance as part of aromaticity

H

(II)
N

(More Electronegativity
& localized lone pair)

NH2

(III)  lone pair is delocalised

CH2NH2

(IV) Lone pair is localised

39. (a)
Sol. As –CHO group is –M, the +M group will decrease C–C bond length, by increasing the double bond
character.
40. (d)
Sol. –M strength order
O O O
|| ||
(a) – C – H >  C  OR >  C  NH 2
(b) –CN > > –CHO > –CH = NH

(c) NO2 > –Ph > NH 2

O O O
|| || ||
(d)  C  H >  C  OCH 3 >  C  NH  C 2 H 5

41. (d)
Sol. HOC  number of CH2 units
1

stability
Also for ring size greater than 11, cis form is less stable than trans.

42. (d)
Sol. (a), (b), (c) have –I effect. In 'd' due to strong +I of –O–, it has + I effect.

43. (d)
Sol. (a) The relative order of +I groups is CH2 > –NH > –O
(b) The relative order of – I groups is
  
NF3 >  N Me3 > – NH 3 > –NO2
(c) The relative order of basic strength in aqueous solution is
Me2NH > MeNH2 > Me3N > NH3

44. (d)
Sol. It is least basic due to maximum –I effect.
45. (a)
Sol. In first compound the negative charge is not in resonance.
46. (c)
COOH COOH

Sol. is more acidic than because of highly acidic –SO3H group.

SO3H
NO2
47. (a)
C N

Sol.

CH=CH–CH=CH2

48. (d)
Sol. (d) Complete octet RS

49. (c)
Sol. Only in (c) the alkene is in conjugation.

50. (c)
Sol. (c) Cyclooctatetraene is non-aromatic due to non-planar tub shape.

51. (d)
Sol. II : (+I) and (+H) of CH3, III : (–I) of NO2, IV : (–M) and (–I) of NO2.

52. (b)
O O
|| 
Sol. (1) CH3 – C – NH2 
 CH3 – C = NH2

NH NH NH
 
(2) NH2– C – NH2 
 NH2 – C = NH2 
 NH2 = C – NH2
More basic due to 3 equivalent RS in conjugat acid.
NH NH
|| 
(3) CH 3  C  NH 2 
 CH3 – C = NH2

O O
..
(4) Ph – C – NH2 
 Ph – C = NH2

53. (b)
Sol. as the compound is not completely conjugated, therefore it is non aromatic.

54. (c)
Sol. (c) has (+M) equal (+M) effect of OCH3 as (b) but user (–I) effect due to greater distance. Mesomeric
effect is distance indendent while inductive effect is distance dependent.
Thus (c) has maximum electron density and is most basic.
55. (d)
a 
Sol. b
H —C — O— CH3 H — C = O — CH3
c
O O
Because of resonance single bond converts to double bond and vice versa. Hence the order of bond
length is b > a > c

56. (c)

Sol.  aromatic
N  N
H H

57. (c)
Sol. Greater the + M greater the stability

58. (c)
1
Sol. Stability of carbanion   EWG
EDG

59. (c)
Sol. The bond which has highest double bond character will be strongest and double bond character
decreases with increase in hyperconjugation.

60. (c)
Sol. Greater the +M effect greater the electron density in the ring.
Order of + M effect : – NH2 > –OH > –CH3 > NO2

61. (c)
Sol. Greater the availability of electrons greater will be the basicity.

62. (c)

–H
Sol.
O OH O O O O O O

[– ve charge is delocalised on both oxygen and thus charge is more stable]

63. (d)
Sol. Greater the resonance greater will be the stability of negative charge.

64. (b)
Sol. The order of acidic strength of the following:
COOH OH SH OH

> > >

NO2
65. (c)
Sol. (c) is most stable due to –ve charge on more electronegative O atom.

66. (c)

Sol. is least stable because double bond at bridge head is unstable. (Bredt's rule)

67. (c)
Sol. Greater the number of carbon atoms in a molecule, greater will be the heat of combustion.

68. (c)
1
HOH 
Sol. Stability of alkene (where no. of -bonds are same)

69. (a)
Sol. Greater the conjugation, greater will be the stability.

70. (c)
1
Sol. Heat of combustion 
Stability

R.S.
71. (I)
O OH

(II) C
H3C C–H2–H H3C CH2
H-atom migrating not possible in resonance

(III) Number of unpaired e–s are not same.

2 unpaired
electrons

(IV)



72. (c)
–I
SO3H–I CN –I COOH –I NO2 –I
Sol.

CF3 –I OH –I
73. (c)
3
sp
O
Sol. (a) S (b) (c) (d)
B 6e–
6e Non-aromatic
H in one loop
Aromatic Aromatic
6e
–

Aromatic

74. (c)

Sol.

75. (b)

OH O O O

Sol.
(Resonance
in one ring)
NO2
N (Extended (Extended
O O
(–M) resonance resonance only)
(highly extended with (–I) of
resonance) –NO2)

76. (c)
NH2 NH2

Sol. NH2 NH CH3 NH H2N NH

'N' is sp3 'N' is sp2 (+M) Guanidine
hybridised hybridised

77. (a)
Sol. All atoms are sp2 hybridisation, so coplanar.

78. (b)

79. (c)
Sol. (c) is most stable due to negative charge on more electronegative O atom.
80. (c)
OH
O
HO O

Sol. > >

HO O O
OH
Aromatic Antiaromatic

81. (d)
Sol. The octet of every element is complete & the positive charge is on nitrogen is more stable than oxygen.

82. (a)
Sol. The electron with drawing CHO group would further increase the polarisation of H bond by stabilising
the –ve change, then increasing the single bond character and decreasing the rotational barrier.

CHO

83. (b)
Sol. Correct orders are as follws :
(a) – NO2 > –CN > –F > –Br
   
(c) – N Me3 > – NH3 > – NH 2 Me > – NH Me2
(d) – Cl > –Br > –OH > –NH2

84. (c)

Sol. NH–Me
(i) (ii)
(Less Hyperconjugation) (Resonance)

NH–Me
(iv)
(iii)
C N
(More Hyperconjugation) (More Resonance)

85. (d)

86. (b)
87. (c)
O – C – C – OH H – C – OH
Sol. (a) <
O O O
+ I effect
(b) I more acidic due to –I of F.
(c) III (resonance stabilised) > I (Lesser –I) > II (More I).
(d) Order is a combined effect of +I effect of ethylgroup and hydration of conjugate acid.

28. (c)
Sol. In a period, lesser the electronegativity, greater the basic strength.
NH2
CH3
is least basic because of SIP. The para isomer is more basic than meta due to +H effect

of CH3 in para isomer.

89. (c)
Sol. Lesser the stability of alkene, greater will be, the heat of hydrogenation.
(c) is least stable as only two  bonds are in conjugation.

90. (d)
H
B
Sol. is aromatic since the empty P orbital of B completes the cyclic conjugation.

91. (d)
Sol. (a) Stronger (–M) of NO2 than (–I) of F makes p-nitro phenol more acidic.

(b) – N F3 is stronger –I group due to (–I) of F..
COOH COOH COOH
(c)
NO2 NO2
SIR, –M NO2 –M
–I

92. (a)

O
Sol. N Like charges are close and undergo repulsion.
O
Highly unstable
93. (b)
Sol. Acidic strength order is opposite of basic strength order

:
NH3 NH2 (c)

:
NH3 NH2
(a)
N N (b)

:
H Basic strength
a>b>c

94. (a)
Sol. (1) and (2) are highly basic due to (+M) effect of NH2 (1) > (2) due to (+M) of OCH3 as opposed
to (–M) of CN.
(3) > (4) since in (4) the lone pair of N undergoes resonance with two C = O groups and is thus less
available for donation.

95. (b)
Sol. The two most acidic H atoms will be abstracted.

96. (c)
Sol. (c) is Guanidine, one of the strongest organic base.It is highly basic due to 3 equivalent RS in its
conjugate acid.
(b) is less basic than c due to lesser +M of the top NH group.

97. (c)
Sol. Sulphonic acid is more acidic than carboxylic acid (c) is more acidic than (a) due to electron withdrawing
effect of the –COOH group.
98. (b)
O O O O
Sol. (I) CH3– C – CH2– C – CH3 C – C – CH – C – CH3
Most acidic Most stable
O O
(II) CH – C – CH
3 3 CH3– C – CH2

(III) CH  CH CH  C
Least acidic Least stable

(IV) CH3– CHO CH2– C – H

O
99. (d)
Sol. (III) is most basic as the lone pair of N is localised IV > II > I as per extent of involvement of lone pair
of N in resonance. More resonance decreases basic strength due to decreased availability of lone pair
for line is donation.
100. (b)


Sol. H
 

Aromatic