Aromatic Hydrocarbon & EAS

1. Which of the following compounds is / are aromatic (i to x)

(i). (A) (B) (C) (D)

(ii). (A) (B) (C) (D)

(iii). (A) (B) (C) (D)

(iv). (A) (B) (C) (D)

(v). (A) (B) (C) (D)

(vi). (A) (B) (C) (D)

(vii). (A) (B) (C) (D)

(viii). (I) (II) (III) (IV)

(A) I, II (B) I, IV (C) I, II, III (D) I, II, III, IV

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(ix). (A) (B) (C) (D)

(x). (A) (B) (C) (D)

(xi). (A) (B) (C) (D)

2. Which of the following compounds is / are not aromatic : (i - iii)

(i). (A) (B) (C) (D)

(ii). (A) (B) (C) (D)

(iii). (A) (B) (C) (D)

(iv) Electrophilic addition of Br2 has been observed in,

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

3. Which of the following is/are antiaromatic

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

4. Which of the following cyclic species disobeys rule.

(A) C20H20+2 (B) C12H12+2 (C) C12H12 (D) C12H122–

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 Br / Fe
2
5.      __________
monobro mination

(A) (B)

(C) (D)

Br2 / Fe
6.  
(1 eq.)

(A) (B)

(C) (D)

Br
2
7.   ____________
CHCl 3

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

8. The most stable carbocation is formed when the electrophile ( E ) attacks upon position

E


(A) 1 (B) 2 (C) 3 (D) 4 (E) 5

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9. Which of the following C6H6 structure give only one C6H5 Br isomer ?

(A) 1, 2, 5 (B) all (C) 1, 5 (D) 1, 4, 5

10. Three dibromobenzenes X, Y, Z melt at 87°, 6° and – 7°C respectively. Number of mononitration
products obtained by X, Y and Z are respectively.
(A) 3, 2 and 1 (B) 1, 2 and 3 (C) 2, 3 and 4 (D) 1, 3 and 2

11. The number of monochloro derivatives of following compounds are respectively

(A) 1, 2, 3, 4 (B) 1, 3, 4, 5 (C) 1, 2, 4, 5 (D) 1, 2, 3, 5

12. The majoro product ‘p’ of the following reaction is


H
 p

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

13. The most probable major product of following reaction is at position

(A) 2 (B) 4 (C) 5 (D) 7

aq. KOH , Cyclisation mononitration

14.   (A)      (B)
HNO / H SO3 2 4

The product ‘B’ is

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

15. Which one of the following compounds will be most radily attacked by an electrophile ?
(A) Chlorobenzene (B) Benzene (C) Phenol (D) Toluene

16. Benzene reacts with acetyl chloride in presence of anhydrous aluminium chloride to form :
(A) acetophenone (B) phenyl acetate (C) chlorobenzene (D) benzoic acid

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17. In Friedel-Crafts reaction the electrophilic reagent is :
 
(A) AlCl3 (B) R C O (C) R C O Cl (D) none of these

18. A

A can be :

(A) (B) (C) (D) no EAS is possible

19. Phenol reacts with Br2 in CS2 at low temp. to give

(A) m-bromophenol (B) o and p-bromophenol
(C) p-bromophenol (D) 2, 4, 6-tribromophenol

20. The reaction of biphenyl with HOCl in presence of a strong acid gives (Major)

(A) (B)

(C) (D)

21. A B
(B) is

(A) (B) (C) (D) all of these

22. Which of the following structures correspond to the product expected when excess of C6H6 react
with CH2Cl2 in presence of anh. AlCl3

(A) (B)

(C) (D)

23. The ortho-para (o/p) ratio of the percentage yield of product isomers formed on mononitration is
minimum with

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

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24. In the following reactions mention the observations as follows :
Substitution : ortho = o meta = m para = p
Rate with respect to benzene slower = s faster = f

(I)

(II)

(III)

(IV)

The correct observation is

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

(A) p, f m, s m, s o, f

(B) m, s m, s m, s p, f
(C) m, s p, f m, s p, f
(D) p, s m, f m, f p, s

25. o/p ratio of the products formed during nitration of alkylbenzene will be nearly one when the alkyl
group attached to benzene ring is
(A) – CH3 (B) – CH2Me (C) – CHMe2 (D) – CMe3

(i ) Cl / Fe
26.  2  Identify the product
( ii) H O, , H
2

Br Br
Cl Br
Cl Cl Cl
(A) (B) (C) (D)

SO3H OH SO3H

Cl2 / Fe HNO3 HNO3 HNO

 (D) HSO

  (E)
NaOH 3
27.   (A)   (B)  
  (C)  
H2SO4 H2SO4  2 4

The compound (E) is :

Cl Cl OH

O2N NO2 OH NO2 Cl

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

NO2

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 O O
|| ||
2 PhLi HC C H
28. + 2Ph3 P   
    X (C16H10 ) ,product X is

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

O
||

29. + Cl  C  Cl   X

(A) (B)

(C) (D)

140C
30. + CH3CH2CH2CH2NH2  X

(A) X is (B) X is

(C) X is (D) X is

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31. The relative rate of electrophilic substitution at ortho, meta and para positions in the following
compound would be

(A) m > p > o (B) p > o > m

(C) o > p > m (D) o > m > p

32. Nitration of the following compound

gives :

(A) (B)

(C) (D)

33. The product of the following reactions is

(A) (B)

(C) (D)

34. The given product can not be formed by which set of reactants in the presence of AlCl3 catalyst.

(A) + (B)

(C) (D) All of these

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35. The product of the following reaction is

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

36. Compound Y, C7H8O is insoluble in water, dil HCl and aqueous NaHCO3. It dissolves in dilute
NaOH. When Y is treated with bromine water it is converted rapidly into a compound of formula
C7H5OBr3. Identify the structure of Y

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

37. X Y

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38. In which case the percentage of meta electrophillic substition product is 100%.

(A) ArCCl3 (B) (C) (D) ArCHCl2

39. Observe the following reaction carefully. Select the correct answer regarding the major product
formed and the relative reactivity of compound X with respect to ethene for the following reaction.

Br (1eq.) / CCl
X= 2   
4


(A) ; much less reactive than ethene

(B) ; much more reactive than ethene

(C) ; much more reactive than ethene

(D) ; much less reactive than ethene

40. when brominated (Br2 / FeBr3) bromination takes place in :

(A) 2 (B) 1 (C) 3 (D) none of these

41. Which of the following is not the correct route to prepare compound 'X'

X =

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 (A) + 

(B)

(C) +

(D)

42. The major product of the following reaction has substitution at position

Br / Fe
2

(A) 1 (B) 2 (C) 3 (D) 4

43. The highest value of o / p ratio for mononitration will be observed in reaction with

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

44. n-propyl benzene will be the final major product in the reaction.

(A) + CH3CH2CH2OH / HF 

(B) + CH3CH2CH2Cl

(C)

(D)

45. The correct order of decreasing reactivity towards an electrophilic reagent is :

Ph - COOEt Ph - NMe2 PhOCOEt Ph

   V
(A)  >  >  > V (B) V >  >  >  (C)  > V >  >  (D)  >  >  > V

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46. Compound A (C10H6) liberates 2 moles of CH4 when treated with Methyl magnesium bromide. On
heating with KMnO4 solution, A produces Benzene dicarboxylic acid which on mononitration
produces only one product and no other isomers. A can be :

(A) (B)

(C) (D)

47. Give the product of the reaction of p-Xylene with NBS

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

48. Major product of the reaction given is

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

49. Which is not the product of the following reaction]

HNO
3
 
H2SO4

(A) (B)

(C) (D)

50. The product of the following reactions is

(A) (B)

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 (C) (D)

51. Product of the following reaction is

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

52. Which will be the correct path to synthesize from

(A)

(B)

(C)

(D)

53. Major product formed by SE reaction in disubstituted benzene has been given. Which is not the
correct formation ?

(A) (B)

(C) (D)

54. Nitration of the following compounds will be in order

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

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 :

55. Consider following -complex of SE reaction on the benzene and its compounds.

+ E+ 

+ E+ 

+ E+ 

Potential energy diagram of the above SE reaction is :

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

56. SE reaction product has been given in each case. In which case orientation is incorrect ?

(A) +

(B)

(C)

(D)

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Passage-1 ( For Question No. 57 to 59)

In SE (electrophilic substitution), aromatic ion (a  complex) is formed in a rate-determining step.



Free energy change associated with addition product and electrophilic substitution has been given
in the diagram. Answer the questions based on this :

57. Which is not the resonance structure of -complex ?

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

58. Which step is not favourable ?

(A) (B)

(C) both the above (D) none of the above

59.

The nitration will mainly take place at position

(A) 1 (B) 2 (C) 3 (D) 4

Passage-2 ( For Question No. 60 to 64)

In monosubstituted benzene derivatives, if the substituent group provides electron density to the
ring by its resonance effect, it is always ortho para directing. The arenes (alkyl benzenes) stabilize
the arenium ion by + I and hyperconjugative effect so are also activating and ortho para directing.
If the substituent group withdraws electron density by resonance effect then it is meta directing. In
case of disubstituted benzenes, the strongly activating group dominates over weakly activating or
deactivating groups in deciding the orientation of major product. There is often little substitution
between two group that are meta to each other due to steric crowding.

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60. In the following reaction the monochlorination mainly take place at

(A) ortho position (B) meta position

(C) para position (D) both at ortho and para position

61. ;

The major substitution is taking place at position

(A) 1 (B) 2 (C) 3 (D) 4

62.

The major product is

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

63. Which of the following aromatic ring is most basic with DF / BF3.

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

HCl Br2 / Fe
H 
64. +  
 
(1) ( 2) (3)

The major product is

(A) (B)

(C) (D)

65. The major monochlorination product of following compound is:

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 (A) (B)

(C) (D)

66. The major product of the following reaction sequence will be

(A) (B)

(C) (D)

67. Which of the following structures correspond to the product expected when excess of C6H6 react
with CH2Cl2 in presence of anh. AlCl3

(A) (B)

(C) (D)

68. 4-Chloro-3-nitro-benzoic is best synthesized by the sequence.

(A) Benzene

(B) Benzene

(C) Benzene

(D) Benzene

69. + CO + HCl

C or D cannot be

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

70. A B
(B) is

(A) (B) (C) (D) all of these

71. A

‘A’ is

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

72. Observe the following reactions

The main factor for such observation with different halogens can be
(A) Polar factor (B) Steric factor
(C) Ionisation of X2 (D) Ionisation of phenol

73. Three dibromobenzenes X, Y, Z melt at 87°, 6° and – 7°C respectively. Number of mononitration
products obtained by X, Y and Z are respectively.
(A) 3, 2 and 1 (B) 1, 2 and 3 (C) 2, 3 and 4 (D) 1, 3 and 2

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74. The most activated benzene ring (which has maximum electron density) is,

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

75. The most stable and the least stable resonating structures are respectively

(A) I and IV (B) I and III (C) II and III (D) III and II

76. Which statement is true for the following reaction

(A) C6H6 and C6D6 react with almost same rate for most of the electrophiles
(B) II is an aromatic species
(C) rate of first step (r1) is faster than rate of second step (r2) in most of aromatic electrophilic
substitution reactions
(D) Electrophilic addition is more favoured than electrophilic substitution in benzene

77. The correct order of resonance energy of the following compounds would be

(A)  >  >  > V (B) V >  >  >  (C)  >  >  > V (D)  >  >  > V

78. Which of the following reactions is least favoured.

(A) (B)

(C) (D)

79. Where the nitration will take place in the following compound ?

(A) 1 (B) 2 (C) 3 (D) 4

80. 1, 2, 4-Tribromo benzene on nitration gives all possible isomers mono nitration products
(A) 1 (B) 2 (C) 3 (D) 4

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 Answers
1. (i) C (ii) A, B, D (iii) A (iv) D (v) C
(vi) A, C (vii) C (viiii) D (ix) B, C (x) A, C, D
(xi) A
.
2. (i) A, D (ii) C, D (iii) D (iv) C

3. C, D 4. C

5. A 6. B 7. B 8. A

9. D 10. B 11. D 12. B

13. D 14. B 15. C 16. A

17. B 18. A, B 19. B 20. C

21. C 22. D 23. C 24. C

25. B 26. C 27. D 28. C

29. D 30. C 31. B 32. C

33. D 34. C 35. B 36. B

37. C 38. B 39. B 40. A

41. A 42. B 43. B 44. C

45. D 46. B 47. D 48. C

37. C 38. B 39. B 40. A

41. A 42. B 43. B 44. C

45. D 46. B 47. D 48. C

49. C 50. D 51. D 52. C

53. D 54. B 55. C 56. A

57. D 58. A 59. D 60. B

61. B 62. A 63. D 64. D

65. D 66. B 67. D 68. D

69. C 70. C 71. C 72. B

73. B 74. D 75. C 76. A

77. C 78. B 79. A 80. C

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