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SHEET – 2 – EAS
ELECTROPHILIC AROMATIC SUBSTITUTION
1. Chlorination of toluene in the presence of light and heat followed by treatment with aqueous NaOH
gives
(a) ocresol (b) pcresol
(c) 2, 4dihydroxytoluene (d) benzoic acid

2. For the electrophilic substitution reaction involving nitration, which of the following sequence
regarding the rate of reaction is true?
(a) k C 6H6  k C 6D6  k C 6T6 (b) k C 6H6  k C 6D 6  k C 6T6
(c) k C 6H6  k C6D 6  k C 6T6 (d) k C 6H6  k C6D 6  k C 6T6

3. Which of the following statement made on FriedelCrafts reaction is false?

(a) Friedel Crafts alkylation and acylation leads to new carboncarbon bond formation.
(b) Alcohol/acid combination can be used as reagent for FriedelCrafts alkylation.
(c) When benzene and nitrobenzene, both liquids, are mixed and treated with
CH3COCl/AlCl3 under proper reaction conditions, the products obtained are macetyl
nitrobenzene and acetophenone.
(d) npropylbenzene can be made in good yield from benzene using npropyl chloride and
anhydrous AlCl 3 combination as reagent at low temperature.

4. The halide that will not react with benzene in the presence of anhydrous AlCl 3 is
(a) CH3CHClCH3 (b) C6H5CH2Cl
(c) C6H5Cl (d) CH3CH2CH2Cl

5. Which of the following species is expected to have maximum enthalpy in an electrophilic aromatic
substitution reaction?

H E+ H E +
H E E
+ +
+ E+ +

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

(a) Species (II) (b) Species (III)
(c) Species (IV) (d) Species (V)

6. The relative reactivities of benzene, aniline, nitrobenzene and toluene are

(a) benzene > toluene > aniline > nitrobenzene
(b) nitrobenzene > aniline > toluene > benzene
(c) toluene > aniline > nitrobenzene > benzene
(d) aniline > toluene > benzene > nitrobenzene

7. During electrophilic substitution the major product in the following reaction will be

FeCl3
+ Cl2 ?
N
H
Cl

(a) Cl (b) (c) (d) both (a) & (b)

N N N
H H Cl

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8. Electrophile NO 2 attacks the following aromatic species.

CCl3 NO2 N H3 O

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

In which cases NO 2 will be at meta position?

(a) (II) and (IV) (b) (I), (II) and (III)
(c) (II) and (III) only (d) (I) only

9. Which one of the following aromatic compounds fails to undergo FriedelCrafts reactions?
(a) C6H5CH3 (b) C6D6
(c) C6H5NO2 (d) C6H5Cl

10. Phenol reacts with bromine in carbon disulphide at low temperature to give
(a) mbromophenol (b) o and pbromophenol
(c) pbromophenol (d) 2,4,6tribromophenol

11. Benzene on reaction with conc. HNO3 in presence of conc. H2SO4 followed by the treatment of Cl2
in presence of FeCl3, gives
(a) 2chloro1nitrobenzene
(b) 3chloro1nitrobenzene
(c) 4chloro1nitrobenzene
(d) a mixture of 2chloro and 4chloro1nitro benzene

12. The major product formed on nitration of N, Ndimethylaniline with conc. H2SO4/HNO3 mixture is
NMe2 NMe2 NMe2 NMe2
NO2 NO2
(a) (b) (c) (d)
NO2
NO2 NO2

13. Which of the following triad of group activates the benzene ring and directs the electrophile to o
and pposition for substitution?
(a) NO2, CHO, COOH (b) OH, O, CH3
(c) OH, SO2OH, NO2 (d) NH2, CHO, SO2OH
O Anhydrous
AlCl3
14. + CH3CH2CCl (X)

The structure of (X) would be

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

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CCl3

Cl2, Fe
15. X. What is X as a main product?

CCl3 CCl3
Cl
(a) (b)
Cl
CCl3 CCl3
Cl Cl
(c) (d)

Cl Cl

16. pNitrotoluene on further nitration gives

CH3 CH3 CH3 CH3
NO2 NO2
(a) (b) (c) (d)
NO2 NO2 O2N
NO2 NO2 NO2

17. The order of reactivity of following compounds

CH3 CH2CH3 CH(CH3)2 C(CH3)3
(I) (II) (III) (IV)
towards electrophilic substitution will be-[where φ = C6H5]
(a) (I) > (II) > (III) > (IV) (b) (IV) > (III) > (II) > (I)
(c) (II) > (I) > (III) > (IV) (d) (III) > (II) > (I) > (IV)

NO2+BF4–
18. CH2 (X). What is the major product (X) in the reaction?
O2N
NO2
NO2
(a) CH2 (b) CH2

O2N O2N

(c) CH2 NO2 (d) both (b) and (c)

O2N

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COCl Anhydrous
19. AlCl3 (X). The major product
+
COCl
H O O
C=O C C
(a) (b)
C=O
H
O O
C C

(c) (d) all of these

O
C Br2/Fe(1eq)
20. N

Br O O
Br

(a) N (b) N

O O Br
C
(c) N Br (d) NH +

21. Which of the following groups are deactivating but o/pdirecting?

(a) Cl (b) CH2Cl
(c) NO2 (d) –NO
22. Which of the following substituted benzenes would furnish three isomeric compounds when one
more substituent is introduced?
Cl Cl Cl Cl
Cl
(a) (b) (c) (d)
Cl

Cl
23. In the given sequence of reaction,
Anhydrous Zn / Hg SOCl2 AlCl3
+ methyl succinic anhydride (A) (B) (C) (D)
AlCl3 Conc. HCl

O O
C CH
2 CHCH3
(a) (A) is (b) (A) is
CH–CH3 CH2
CO2H CO2H
Me
(c) (D) is (d) (D) is
Me
O O

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24. Which of the following are not a suitable method to prepare, PhCH2CH2Ph?
Anhydrous
(a) 2PhH + CH2Cl2   

AlCl 3

Anhydrous
(b) PhH + ClCH2CH2Ph   

AlCl3

Anhydrous
(c) PhH + CH3CHPh   

AlCl 3
Cl
Anhydrous Zn / Hg
(d) PhH + PhCH2CCl   
   
AlCl 3 Conc . HCl
O

25. A chiral compound (A) with molecular formula C10H12 do not decolourize Br2 water but can be
oxidised to phthalic acid. The possible structure of (A) could be
H Me
Me
(a) (b)
H
Me Me
(c) H (d) H
Me H
H Me

SMe2

26. What are the correct statements about the given compound, ?
(a) The compound is more reactive than benzene towards electrophilic substitution.
(b) The compound is less reactive than benzene towards electrophilic substitution.
(c) The incoming electrophile will be directed towards orthopara position.
(d) The incoming electrophile will be directed towards meta position.
27. Which of the following compounds are meta directors?
CH2Cl CCl3

(a) (b)

 
NMe3 CH2NMe3

(c) (d)

HF, 0°C
28. + CH3CH=CH2 (A)

Anhydrous
+ CH2=CHCH2Cl (B)
ZnCl2

Which are correct about (A) and (B)?

CH3
CH CH2CH=CH2
CH3
(a) (A): (b) (B):

CH3
CH2CH=CH2 CH
CH3
(c) (A): (d) (B):

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29. Which of the following statements is correct?
(a) Bromination of toluene occurs faster than that of benzene.
(b) Nitration of toluene is easier than that of nitrobenzene.
(c) The bromonium ion is a good nucleophile.
(d) Effective nitrating agent is nitrate ion.

30. Which of the following combination of reagents or sequence of reactions can give linear alkyl
benzene (LAB)?
Anhydrous
(a) + CH3CH2CH2Cl ?
AlCl3, 

FeCl3
(b) + CH3CH2CH2Cl ?

Anhydrous Zn / Hg
(c) + CH3CCH2Cl ?
AlCl3 Conc. HCl
O
Anhydrous Zn / Hg
(d) + CH3CH2CCl ?
AlCl3 Conc. HCl
O

ANSWER KEY
SHEET – 2 – EAS
ELECTROPHILIC AROMATIC SUBSTITUTION

1. (d) 2. (c) 3. (c) 4. (c) 5. (a)

6. (d) 7. (a) 8. (b) 9. (c) 10. (b)

11. (b) 12. (a) 13. (b) 14. (a) 15. (b)

16. (a) 17. (a) 18. (d) 19. (c) 20. (c)

21. (a, d) 22. (a, c) 23. (b, d) 24. (a, c) 25. (a, d)

26. (b, d) 27. (b, c, d) 28. (a, b) 29. (a, b) 30. (b,c,d)

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