AROMATIC COMPOUNDSE

(Only one option is correct)

Single Choice Questions :
NO2 NH2
NO2
Nitrating
(A) (B)
1. Mixture

Given reaction is an example of

CF3
(A) Substitution electrophilic aromatic (SEAr)
(B) Substitution nucleophilic aromatic (SNAr) (C) (D) All of these
(C) Electrophilic addition reaction (EAR)
(D) Bi molecular nucleophilic substution (SN2)

6. Most reactive towards nitration reaction (Sub-

stitution electrophilic aromatic)
E – Nu
2.
NH2

Name of intermediate produced during given (A) (B)

reaction will be
(A) Arenium ion
(B) -complex/wheeland intermediate O
(C) Nonaromatic cyclohexa dienyl carbocation
NH N
(D) All of these

(C) (D)
3. Which of the following reagent is best when
friedel craft Halogenation takes place
(A) HO–
(C) AlCl3 (hydrated) (D) All of these
7. Which of the following compound gives ben-
zoic acid when it reacts with hot KMnO4 fol-
4. WHat is the name of electrophile when ben- lowed by acidification.
zene goes nitration
(A) Nitrosonium ion (B) Nitronium ion
(C) Halonium ion (D) Alkyl carbocation (A)

O H
5. Which of the following compound gives poor CH 3
yield in friedel-craft reaction
(B) (C)

(D) All of these

 AROMATIC COMPOUNDS Page # 7

CF3 O
Conc. HNO 3
8. + Major product 11. + AlCl3
O  
Conc.H2SO4

CF3 CF3 O

NO2 Zn(Hg)
(A) HCl
  (B) 
conc.H2SO4
   (C) (Major prod-
(A) (B)
uct)
NO2 C will be :
CF3

(A) (B)
(C) (D) A and C both

O
NO2

OCH3
(C) (D)
O
9. Nitration Major product

12. How many  electron are there in the follow-

F ing speices :
OCH3
OCH3

NO2
(A) (B)
NO2
(A) 2 (B) 4
F (C) 6 (D) 8
(C) Mixture A and B F of these
(D) None

13. Ease of ionization to produce carbocation and

NH2 bromide ion under the treatment of Ag will be
maximum in ?
NaNO2 H 2O
10. (A) (B)
2HCl Boil O

Product (B) will be : (A) (B)

OH
Br
Br
(A) (B)

+ –
N2Cl Cl (C) (D)

(C) (D) Br Br
 Page # 8 AROMATIC COMPOUNDSE


Cl In which cases N O2 will attack at meta posi-
14. 2SbCl5 tion
   P ; P will be
Cl
(A) II and IV (B) I, II and III
(C) II and IV (D) I only

(A) 2– (B) 2+ 2SbCl6–

18. Increasing order of the following for electrophile
substitution reaction as -

(C) (D) Mixture of A & B

(I) CH3 (II)

15. Which order is correct for the decreasing re- (III) COOH
activity to ring monobromination of the fol-
lowing compounds : (A) I > II > III (B) III > II > I
(I) C6H5CH3 (II) C6H5COOH (C) II > III > I (D) I > III > II
(III) C6H6 (IV) C6H5NO2
(A) I > II > III > IV (B) I > III > II > IV 19. Which of the following will form tri-bromo de-
(C) II > III > IV > I (D) III > I > II > IV rivative of phenol ?

OH OH
16. Which of the following order is correct for the
decreasing reactivity to ring monobromination Br2 Br2
(A)   (B)  
of the following compounds : HO 2 H2O

CH 3 COOH

(I) (II) OH OH

Br2 Br2
(C)   (D)  
COOH NO2 CS 2 H2O

(III)

Ph
(A) I > II > III > IV (B) II > III > IV > I
(C) I > III > II > IV (D) III > I > II > IV HBF4
20. O–Ph   Product of this

 Ph
17. Electrophile N O2 attacks the following : reaction is :

CCl3 NO2 OH
Ph
(I) (II)
(A) Ph H+

CHO O Ph

(III) (IV)
 AROMATIC COMPOUNDS Page # 9

OH 23. Benzene reacts with n-propyl chloride in the

Ph presence of anhydrous AlCl3 to give predomi-
nantly :
(B) + Ph OH
(A) n-Propylbenzene
(B) Isopropylbenzene
Ph
(C) 3-Propyl-1-Chlorobenzene
Ph
(D) No reaction
(C) Ph OH +
24. In the sulphonation, acetylation and formylation
Ph of benzene the group of effective electrophiles
Ph would be :


Ph OH (A) SO3+, CH3C  O+, H C O
(D)

Ph 
(B) SO3, CH3 –C  O+, H C O

(C) SO3, CH3CHO, CO + HCl

NO2 (D) HSO3, CH3CO, HCO

(1)NaOH
21.   
 (A), Product (A) is
(2)H3O 25. p-Nitrotoluene on further nitration gives :
I

Br CH3
CH3
NO2
NO2
NO2
(A) (B)

NO2
(A) (B) NO2
OH NO2
I
Br
OH
OH NO2 CH2OH CH3

OH NO2 NO2
(C) (D)
(C) (D)
I I O2N

Br Br NO2

22. For preparing monoalkyl benzene, acylation

process is preferred than direct alkylation be- 26. The major product formed on monobromination
cause of phenylbenzoate is :

(A) In alkylation, a poisonous gas is evolved

Br
(B) In alkylation, large amount of heat is evolved
(C) In alkylation, pollyalkylated product is O
formed (A)
O
(D) Alkylation is very costly
 Page # 10 AROMATIC COMPOUNDSE

28. The major product formed in the reaction is :

OMe
3 AlCl
O + (CH3)2 CHCH2Br 
Br
(B)
O
OMe

(A)
CH 2CH(CH 3) 2
Br
OMe
O
(B)
(C) (CH3 )2CHCH2
O
OMe

(C)
C(CH 3) 3
OMe
O
(D) (D)
O (CH3 )3 C
Br

29. In the sulhponation of benzene, the active elec-

27. The major product formed in the reaction is : trophilic species is :
(A) SO2 (B) SO3
+ (C) SO42– (D) HSO4–
OCH3 + E
(electrophile)
30. Which one of the following compounds under-
goes bromination of its aromatic ring at the
(A) OCH3 fastest rate ?

E
(A) (B)
(B) E OCH3
N
|
H
OCH3
(C)
E NH
(C) (D)
NH
OCH3 O
(D)
E 31. In the reaction the major product formed is :
O

Br2 (1mole)
N    
Fe
 AROMATIC COMPOUNDS Page # 11

O 33. Increasing order of rate of reaction with Br2/

Br AlBr3 is :
(A) N OCH3 OCH3

O
(I) (II)

N
(B)
O OCH3
Br
O
O
(III) (IV)

N
(C)
(A) III < I < II < IV (B) III < II < I < IV
(C) II < IV < III < I (D) IV < II < III < I
Br
O
34. What combiantion of acid chloride or anhy-
(D) N Br dride and arene would you choose to prepare
given compound ?

32. HNO / H SO
 3 
2 4

  (A) Ma-

MeO C–CH2–CH2–CO2H
jor product : O

NO2

NO2 O O
(A) AlCl3
(A) + Cl–C–CH2–CH–C–Cl
MeO
CH3
NO2
(B)
O
MeO

(B) + AlCl3
O  
NO2
(C) O
MeO

O
(D)
NO2 (C) + AlCl3
MeO O  

O
 Page # 12 AROMATIC COMPOUNDSE

37. Which of the following is most reactive toward

O SNAr :

(D) + AlCl3
  Cl Cl
NO2
O
(A) (B)

NO2 NO2
35. Which position will be attacked most rapidly
+
by the nitronium ion (NO2 ) when the com-
pound undergoes nitration with HNO3/H2SO4 :
Cl
(I) (II) (III) (IV) Cl
O2N NO2
H 2C
OCH3 (C) (D)
H3 C
NO2
NO2
(A) I (B) II
(C) III (D) IV

Cl
36. Identify (C) in the reaction(s)

HNO3 CH3ONa
CH3 38.   (A)   (B) Major,,
 

NaNO2 / HCl

H O, 
  (A) 2 Cl
0C Product (B) is

Cl Cl
NH2

(i)CHCl ,KOH, 
(B)   3   (C) (A)
NO2
(B)
(ii)[Link] OCH3
OCH3 Cl
CH3 CH3 OCH3 Cl
H3
CHO OC
(A) (B)
(C) (D)
CHO NO2 NO2
OH OH Cl Cl

CH3 39. The major product formed in the reaction is :

(C) (D) None of these

CHO
conc.H2SO4
+ HNO3    
Cl
 AROMATIC COMPOUNDS Page # 13

(A) Lindane (B) DDT

NO2 (C) Caprolactum (D) Nylon-6

(A) (B)
NO2 AlCl3
43. C6H6 + A   C6H5CONH2

A in the above reaction is :

NO2 (A) NH2CONH2 (B) ClCONH2
(C) CH3CONH2 (D) CH2(Cl)CONH2

(C) (D)
CH3COCl ZnHg
NO2 44. C6H6 AlCl
  A    B
3 HCl

The end product in the above sequence is :

40. CrO2Cl2
C6H5CH3  H2O
  A   B
 (A) Toluene (B) Ethyl benzene
The functional group present in B and name of (C) Both the above (D) None
the reaction would be
(A) –CHO, Gattermann aldehyde synthesis
(B) –CHO, Etard reaction
45. AlCl3
+ CH3–CH2–CH2–CH2–Cl 
(C) –COCH3, Fridel Crafts reaction 
(D) –CHO, Oxo reaction
hydrocarbon (X) major product X is
41. Which chloroderivative of benzene among the
following would undergo-hydrolysis most
readily with aq. NaOH to furnish the corre- (A) CH2CH–CH3
sponding hydroxy derivative.
CH3
NO2
CH3
(A) O2N Cl
(B) C–CH3
NO2
CH3

(B) O 2N Cl

(C) CH2CH2CH2CH3

(C) Me2N Cl (D) None of correct

46. Reaction of SO3 is easier in :

(D) Cl
(A) Benzene (B) Toluene
(C) Nitrobenzene (D) chlorobenzene

Cl conc.H SO4
47. The mixture of the following four aromatic com-
42. Chloral +   2   prod- pounds on oxidation by strong oxidising agent
gives :
uct. The produt is :
 Page # 14 AROMATIC COMPOUNDSE

CH3 C2H5
Ni,High temp.
52. + H2      (A). Which of
high pressure

the following can be isolated as the product

of this reaction.
CH2 OH CHO

and (A) (B)

(A) Mixture of C6H5CH2OH+C6H5COOH

(B) Mixture of C6H5CHO + C6H5COOH (C) (D)
(C) C6H5COOH
(D) None of the above
53. Which of the following is/are produced when a
mixture of benzene vapour and oxygen is
48. Methyl group attached to benzene can be passed over V2O5 catalyst at 775 K ?
oxidised to carboxyl group by reacting with :
(A) Oxalic acid (B) Glyoxal
(A) Fe2O3 (B) AgNO3 (C) Fumaric acid (D) Maleic anhydride
(C) KMnO4 (D) CrO3

54. Which of the following is the least reactive in

CH=CH2 the case of bromination ?
(A) Phenol (B) Aniline
Br2 (C) Nitrobenzene (D) Anisole
49. A 
CCl
KMnO4 / 
   B
4

Compound A and B respectively are : F

55. Above compound undergoes
(A) o-Bromostyrene, benzoic acid
(B) p-Bromostyrene, benzaldehyde NO2

(C) m-Bromostyrene, benzaldehyde

(A) SN1
(D) Styrene dibromide, benzoic acid
(B) SN2
(C) Elimination
50. The number of benzylic hydrogen atoms in (D) Nucleophilic aromatic substitution
ethylbenzene is :
(A) 3 (B) 5
56. Benzene on reaction with ‘A’ forms
(C) 2 (D) 7
O

51. The highest yield of m-product is possible by

the electrophilic substitution of the which on reaction with
following :
(A) C6H5CH3
(B) C6H5CH2COOC2H5
(C) C6H5CH(COOC2H5)2 ‘B’ forms ‘A’ and ‘B’ are:
(D) C6H5C(COOC2H5)3
 AROMATIC COMPOUNDS Page # 15

61. Ring nitration of dimethyl benzene results in

O
the formation of only one nitro dimethyl ben-
(A) Zn (Hg) + conc. HCl, zene. The dimethyl benzene is :
Cl
O CH3
(B) , LiAlH4 CH3
Cl (A) (B)
CH3
CH3
O
(C) , NaBH4 CH3
Cl
O (C) (D) None of these
(D) , Zn(Hg) + [Link]
Cl
CH3
+ AlCl3
62. if p-methoxy toluene is nitrated, the major
57. In a reaction of C6H5Y, the major product product is :
(>60%) is m-isomer, so the group Y is : CH3 CH3
(A) –COOH (B) –Cl
(C) –OH (D) –NH2 NO2

(A) (B) NO2

58. Which of the following will undergo sulphonation
at fastest rate ? OCH3 OCH3
CH3NO2

(A) (B) (C) (D) No reaction

OCH3

63. An aromatic compound of molecular formula

(C) (D) C6H4Br2 was nitrated which gives three iso-
mers of formula C6H3Br2NO2 were obtained. The
original compound is :
59. Which of the following is most reactive to- (A) o-dibromobenzene
wards sulphonation ?
(B) m-dibromobenzene
(A) m-Xylene (B) o-Xylene
(C) p-dibromobenzene
(C) Toluene (D) p-Xylene (D) both A and C

60. When sulphonilic acid (p-H2NC 6H4SO 3H) is N

treated with excess of bromine water the prod-
uct is: 64. + Ph – N2+Cl–  (A) major product A
(A) tribromo product
(B) dibromo product will be
(C) monobromo product
(D) tetrabromo product
 Page # 16 AROMATIC COMPOUNDSE

67. For the electrophilic substitution reaction in-

N
N volving nitration, which of the following se-
quence regarding the rate of reaction is true ?
N = N – Ph
(A) (B) (A) K C6H6  K C6D6  KC6 T6

N = N – Ph (B) K C6H6  KC6D6  K C6 T6

N N
(C) K C6H6  K C6D6  KC6 T6

(D) K C6H6  K C6D6  K C6 T6

(C) (D)

Ph Cl 68. For the electrophilic substitution reaction in-

volving sulphonation, which of the following
seqence regarding the rate of reaction is true
65. Which of the following carbocations is expected
to be most stable ?
(A) K C6H6  K C6D6  KC6 T6
NO2 NO2
(B) K C6H6  KC6D6  K C6 T6
+
(C) K C6H6  K C6D6  KC6 T6
(A) (B)
+
(D) K C6H6  K C6D6  K C6 T6
H Y H Y
NO2 NO2
+ H 69. WHich of the following structures correspond
(C) Y (D) to the product expected, when excess of C6H6
H reacts with CH2Cl2 in presence of anhydrous
+ Y
AlCl3 ?

Cl
66. Which of the following species expected to
have maximum enthalpy in an electrophilic aro- (A) CH
matic substitution reaction ?

H E
(B) CHCl2

(I) + E+  (II) 
Cl
H E H E C
(C)
(III)  (IV)  Cl

(D) CH2
E

(V)
70. Identify the correct order of reactivity in elec-
trophilic substitution reactions of the follow-
(A) Species (II) (B) Species (III) ing compunds:
(C) Species (IV) (D) Species (V)
 AROMATIC COMPOUNDS Page # 17

C2H5 CH3
|
(1)CH3  C H  CH2Cl / AlCl3
(C)         
(2)HNO3  H2SO 4
(I) (II)
(1)HNO  H SO
 CH3 
2 4

 
Cl (D) 3
NO2 |
(2)CH3  C H  CH2Cl / AlCl3
Cl NO2
(III) (IV)
73. Which of most reactive towards nucleophilic
aromatic substitution.
(A) I > II > III > IV (B) IV > III > II > I
(C) II > I > III > IV (D) II > III > I > IV F F

(A) (B)
71. Conjugation of electron withdrawing groups,
O O
CH3 NO2
e.g., –CHO, – C – R , – C – OR , –C  N, –
NO 2 activates nucleophilic attack in Cl I
halobenzene. The order of reactivity of these
group towards nucleophilic aromatic substitu-
tion. (C) (D)

O O O NO2 NO2
(A) –NO2 > –C  N > –C–H > – C – R > – C – OR

O 74. Which is the best synthesis of

O O
(B) –C–H > – C – R > – C – OR > –C  N > –NO2 CH3O NO2 ?

O O O NO2

(C) –C  N > –NO2 > –C–H > – C – R > – C – OR

Br2 HNO3 HNO
3
(A)        
FeBr3 H2SO 4 H2SO 4
O O O
NaOCH
3
   
(D) –C–H > –NO2 > –C  N > – C – OR > – C – R CH3OH

HNO3 HNO
3 Br2
(B)     
72. Choose the best method to prepare given com- H2SO 4 H2SO 4 FeBr3
pound :
NaOCH
3
   
CH3OH
H3C
H3C NO2 HNO Br HNO
3 2 3
(C)         
H3C H2SO 4 FeBr3 H2SO 4

NaOCH
3
   
CH3OH
(1)HNO3  H2SO4
(A)   
(2)Me3CCl / AlCl3
HNO
3 2 3 Br NaOCH
(D)          
H2SO 4 FeBr3 CH3OH
(1)Me3CCl / AlCl3
(B)      

(2)HNO3  H2SO4 HNO
3
  
H2SO 4