Reaction Mechanism 481

-------

[G-1)]
Electrophilic Substitution Reactions (Aromatic)
1. Which of the
han benzene following
toward ring compounds is more where
electrophilic aromatic
bromination ? reactive 5. Identify the site
substitution takes place ?
OH
NH CH,
(a
(b) b
(d) d
(b) b (c) c
(a) a
Identify the site where electrophilic aromatic
6.
substitution takes place ?
CH, H-N

(C

b
2. Compare rate of EAS (d) d
(a) a (b) b (c) c
O Na OH Which of the following represents the best reagent(s)
NH, 7.
for the electrophilic nitration of benzene?
? -NO,
(a) (b) (C) (a)
(a) a> b>c>d (a) NO2 (b) HNO 2
(b) a>c> b> d
(c) c> a> b> d (c) HNO, (d) H,SO4, HNO 3
(d) c> b> a>d
8. Predict the major product of the following reaction.
CH3 NO,
FeBra
Br2
3. (a) o-bromonitrobenzene and p-bromonitrobenzene
b
(b) m-bromonitrobenzene
(c) o-bromoaniline and p-bromoaniline
Identify the position where EAS (Electrophilic (d) m-bromoaniline
Aromatic Substitution) reaction takes place:
9. Predict the major product of the following reaction.
(a) a (b) b (c) c (d) d OH
4. Compare rate of EAS (Electrophilic Aromatic
HNO.
Substitution): H,SO,

CI Ç-OCH, CCH, NO,

(a) 2,4-dinitrophenol (b) 3,4-dinitrophenol
(c) 2,4,6-trinitrophenol (d) 3,4,5-trinitrophenol
CH,
(a) (b) C) ()
(b) b> a>c>d
10. ’ ortho-complex (r);
(a) a > b>c>d
(c) d >b>c>a (d) d > b >a>c
 NCERT Chemistry Booster-XI
482
CH, (a) i (b) ii
(c) ii (d) iand iiequally
meta-complex (r,).Rate of reaction is: (e) i and ii equally
product that results when
(a) r >a (b) r, > 14. What is the major organic
1-chlorobutane and Alci,?
benzene is treated with (b) Isobutylbenzene
(c) r, =
11, Which of the following structures is the most (a) Ethyibenzene
(d) sec-butylbenzene
(c) Butylbenzene
important contributor to the resonance hybrid
formed when toluene undergoes para-nitration ? (e) sec-butylbenzene
following compounds undergoes
ÇH, CH, 15. Which one of the ring (electrophiljc
brominatíon of its aromatic
fastest rate ?
the
aromatic substitution) at
(1) (i) e
H NO, NO, (b)
(a)

ÇH3 ÇH, H

(C
(d)
(ii) (iv) NH NH
H NO, H NO2
(a) i (b) ii (c) ii (d) iv
reaction,
12. Which of the following structure is the most 16. The compound X in the
important contributor to the resonance hybrid + ICI anhydrous AlGl3, Xis :
formed when anisole undergoes obromination ?
OCH, OCH,
Br Br

(i) H (iü) H (b)

(a

OCH, eOCH, Br
Br
(iii) H (iv) H
(d) |
C
(b) ii (c) iii (d) iv
(a) i
reaction ?
13. What is the major product of the following 17. What is the major product of the following
reaction ?
CH3 OH
FeBrg
+Br, ?
HNO3 ’?
H,S04 CH,
CH, NO, CH, OH OH

(i1) (a) CH, (b)

Br cICH,
NO,
OCI Br
CH,
(c) ()
(iii) CH CH
NO,
Reaction Mechanism 483
OH
C
(e)
CH Br
(iii) +CH,NO2

18. Cumene NO, NO,

Dis prepared by: CH,
(iv)
CH,
(a) | +
AlCla (b) ii
(a) i
(d) iv
(c) iii
(b) + Alcl,. (e) no reaction

(c) H+ ’(A),
22. AlCl

Product (A) is :
(d) All of these
19. Which of the following is the electrophile that attacks
the aromatic ring during Friedel-Crafts acylation ?
O=0
(a) R-C-CI (b) R-C=0 =0
(a) (b)

(c) R-C AlCl, (d) R-C-C|Cl

CI
20. In electrophilic aromatic substitution reactions a
chlorine substituent:
(a) is a deactivator and a m-director
(b) is a deactivator and an o, p-director
(c) is an activator and a m-director =0
(d) is an activator and an o, p-director
(d) PhC-Ph
21. What is/are the product(s) from the following
reaction?
NO2
Cl
CH,C1’ ?
ACi, CH¡
NO2 NO2 23. +
CHyÇ-CH,Cl AlCl3
CH3 CHg
Major product of the reaction is:
H,
(a t
NO2
(d)
(i)
~CHg
 NCERT Chemistry Booster.y
484)
NHCOPh
(d)
24. 0 ACh(A),Product (A) is:
CHg
26. In Reimer-Tiemann reaction molecular weight of
OH phenol increases by:
(a) Ph (c) 30 (d) 31
(a) 28 (b) 29
OH

NaOH >(A); Product (A) ig:

OH 27. + CHCI, +

(b) OH
QH
CHO
(b
(a
CHO

(C) OH
OH

(d co,H
(c)

(a)
o,H
28. Which of the following compound give:
Reimer-Teimann reaction ?

25. Give the major product of the following reaction: NO,

CH,Cl, AlCl,
NHPh

OH NO,
OMe
NHPh
(a) (d)
H,C

29. Which of the following compound will not undergo

NHPh
Reimer-Tiemann reaction?
(b)
NO2
CHs (a) (b
-NHCOPh
ÇHO
(c)
H,C"
(c) (d) All of these
 geaction Mechanism 485
30. Electrophile in

(a) Ci,
Reimer-Tiemann reaction is: QH

(b) CH,Cl, OH
(c) CHCI,
(d) ¿ccl, (b)
(a) NH,
OH
LOMe NH,
31. () KOH, CHC3,p',
(i) H,0® OH
Major product (P) of the reaction is:
OH
QH
OMe (c) (d)
(a)H

OH
OMe OH N=NCI
H
(b)
33.

OH OCH3
Product of the reaction is:
OMe
OH
(c)
(a)
H
ÖCH3
QH
(b)
(d) CH,0

OMe
OH
32. Consider the reaction;
OH N,+CI
OH
’X;here X is:
ÒCH3
NH,

(d)
HO
 486
NCERT Chemistry Booster-X
OH

OH QH
(e)

(a) (b)
ÖCH,
34. Which of the following is o/p director for EAS CHg CH,
(Electrophilic Aromatic Substitution) ?
OH OH OH
NH CH,
-NH-CH,
(d)
(a) (b) co,H
CHg CH3

CHg NO, +CHCI, + KOHA); Product (A) is:

(c) 36.

OH

QH
35. +CHCl, +NaOHA); Product (A) is:
2H®
(a)
CHg

Answers

1. (a) (b), 3. (b) 4. (d) 5. (c) 6. (b) 7. (d) 8. (b) 9. (a) 10. (a)
11. (a) 12. (d) 13. (c) 14. d) 13. (b) 16. (b) 17. (e) 18. (d) 19. (b) 20. (b)
21. (e) 22. () 23. (b) 24. (a) 25. (c) 26. (b) 27. (a) 28. (c) 29. (d) 30.
31. (c) 32. (a) 33, (c) 34. (a) 35. (b) 36. (b)
Reaction M
Mechanism 487
[G-2]|
Electrophilic Substitution Reactions (Aromnatic)
1. The major
product of the following reaction is

(a)
H,SO4,
(a) a (b) b
(c) c (d) d
6. Electrophile used in coupling reaction is :
(c)
(d) (b)
RN
(a)
2. A
dichlorobenzene
mononitro which
derivative is : on nitration gives only
one CH,G,
C1 (c) (d) None of these

(a)
(b) 7. The most appropriate solvent for Friedel-Crafts
reaction is :
NH2
(a)
(a)
Cl CI NO2 ÇH3
3. The attacking electrophile during nitration of (c) (d)
aromaticcompound in case of mixed acid is :
(a) NO 8. The major product obtained from the following
(b) NO;-OH2 reaction is

(c) NO 2 (d) NO2 Anhy.

C1 AlCl3
4. The most favourable site for attack in the
compound towards
following
electrophilic aromatic
substitution is (a) (b)

(c) (d) Both (b) and (c)

(a) p (b) q 9. The most appropriate site for

electrophilic attack is
(c) r (d) s CH
5. The most appropriate site for electrophilic
substitution in compound is
(a) p (b) q
(c) r (d) s
488 NCERT Chemistry Booster-XI
10. The major product obtained in the following reaction
is
OH
(II)
()NaOH () (II)
+ CHCI, (ii) Slight H+ (b) I> III> II
(a) I> II> III
(d) Il> I>II
OH (c) II> l>I
correct order of
CHO ÇOOH 14. Among the given compounds the aromatic
HO, OH decreasing reactivity towards electrophilic
substitution is :
(a) (b)
CH,
OH HO» (1)
OH OH
()
CHO
OCHg CF3
(c) (d) (IV)
(III)
C
OH OH (b) II> I> II>V
(a) II> I> III> V
11. The major product obtained during the reaction is (d) I> I> II> V
(c) IV> I> II> III
H* 15. The electrophilic aromatic substitution of a
mainly a meta
compound CeH,Y produces following, which
disubstituted product. Among the
Y?
HO" one could be the substituent
(a) -NH, (b) -CH,
(d) -ci
(c) -COOH
(a) of benzene
16. The correct order of increasing reactivity towards
(), anisole (I1) and chlorobenzene (II)
nitration is :
(a) II<I<II (b) III<I<II
(d
(c) I<II<II (d) II< II<I
17. Consider the following compounds I to IV for their
12. The final organic product obtained is reactivity towards aromatic substitution with a given
CHs electrophile. The order of decreasing reactivity is :
CHO
N(CH)2
() (I)
() HNO,/H,SO4
(i) Sn/HCI
CI
CH,
(III) (I)

(a) CH3 (b
(a)III> I>II> V (b) I> II> V>II
(c) I> II> II> V (d) II> IIl> I>V
NH, NH,
18. Among the following compounds, the one which can
OH be most readily sulphonated in the ring is :
NH, CN NO,
(d) (b)
NH,
CH,
13. Arrange the following in decreasing order of rate of (c) (a)|
eletrophilic aromatic substitution.
Reaction Mechanism
19. Which of 489
the
elthenectrbenzene following compounds
ophilic aromatic
(a)
substitution at a slower
CH3under identical undergrateoes
conditionsNH,? (c)
(d)

H H
(b
is most reactive
towards
OH 25. The compound whichsubstitution is :
electrophilicaromatic
(b) Phenyl benzoate
(a) Benzophenone
(d) Benzoic acid
20. The order of (c) Ethylbenzoate
decreasing reactivity of the
towards an electrophilic 26. The fastest rate of electrophilic
aromatic substitution
compounds
identical conditions is : aromatic substitution under
is observed in :
CI

() OCOCH3 (1) NMe, (a) (b)

(I)
NH,CI
(IV)
(C)
(a) II>I> III> V
(b) II> I> IV>III
(c) I> III> II> V
(d) II> V >I> III 27. The most favourable site for electrophilic aromatic
21. Bromination of
benzene must be
presence of reagent'X.'X is : carried out in the substitution is in compound
Br

X
+ Br,
pz
(a) CCl4 (b) NaBr (c) FeBrg (d) HBr CH,
22. The compound in which'p' site is more reactive than (a) P (b) Q (c) R (d) S
'd site towards electrophilic aromatic substitution 28. The product obtained in the following reaction is
reaction is :
+ CCIA Anhy.AlCl3

(b) (Excess)

(a) Ph -CCl, (b) Ph CCi,

(c) Ph,CCl (d) PhC
(c) ()
29. In the given compound, during bromination
electrophile attacks at position
H b
23. The electrophilic aromatic substitution is mainly
observed in the following compound is at site

CH=CH-C OH

(b) q (c) r,p (d) s

(a) p,q
24. Which compound is aromatic ? (a) a (b) b (c) c (d) d
(b)
(490
NCERT Chemistry Booster-KI
30.
During the following reaction, which intermediate is 33. Which of the following CoH, structures
does e
dominantly appeared? have anyrbond ?
CH,
Anhy. AlCl,
(a)
H,c CH2

(c)

34. Consider the following reaction

:
(a) OMe

reaction is :
Ph
The major product formed in the OMe
OMe
31. On reaction of (phenyl benzoate)
(a)
with Br,, the major product obtained is : OMe OMe
(c) (a)
Ph
(a) (b) 35. p-Nitrotoluene on further nitration gives :
Br (a) 3,4-dinitrotoluene
Br (b) 2,4- initrotoluene
(c) 2,6-dinitrotoluene
Ph Ph (d) 2,4-dinitrobenzoic acid
(c) (d) 36. The major product 'R' obtained in the following
Br reaction is:
Br CH,C1 HNO,
Anhy.
+AC,P Anhy Ald, s0,
32. The major product obtained in the following reaction
is
QH NO,
b)
NO2
OH QH NO2
Br Br Br NO2
(a) (b) (d)

Br Br

OH QH 37. The major product obtained in the following reaction

is
Br Br
(c) (a) OCH,
HNO,
Br Br H,SO4
Reaction Mechanism 491
OCH, OH
OCHg (d)
reaction is
product of the following
NO, NO,
42. The final
() Anhy. AlCl,
|+ CH-C=N+ HCI () H,0,
OCH, CN
(c) CH,
(d) None of
these (b)
(a
38. The most reactive
electrophilicaromatic aromatic
substitutioncompound
is : towards CH,
Cl
(a) (b)
(d)
H

43. In the given reaction

q9, Benzene 1s converted in (CH-C0);0A ACla2 BH0C the product

reagents
para-nitrophenol by using Pyridine
) dil. NaOH () HNO,/H,SO4 (C) will be:
(II) Br,/Fe NH, NH,
The most suitable sequence of these reagents are
respectively (a) (b)
(a) I, II, II (b) I, II, I
(c) II, I, I CH, CH,
(d) III, II, I
40. The final major organic product is HNCI NH,
Br,
(d)

Br Br CH,CI CH,CI
(a)
44. Rank the following compounds in order of decreasing
reactivity for nitration.
Br Br

(d
Br

41. Picric acid is obtained in good yield in reaction:

OH (ii) -OCH3
(a dil.
HNO,

OH
(ii) Br- HO-coct,
conc.
(b conc.
H,S0, HNO,
(iv)
H,C -CH¡
OH
conc.
HNO3 Select the correct answer from the following:
 (492 NCERT Chemistry Booster.X
(a) iv > ii>i> ii
(b) ii> iv> ii>i
COCI COOH -------.
(c) ii> iv > i> iii
(d) i> ii> iii > 0v
t . The major product [Xlof the given (a)
reaction is : Br
O,N -OCH, + CH CIAeg[xJ OCH3
CH, (CH3),C=CH,/H
48. ’ Major product is :
(a) O,N -OCH, CH

CH, OCH3 OCH,

C(CHJ)3
(b) H,C0 -NO, (a) (b)
C(CH),
CH, CH3 CH,
(c) O,N -OCHg
H,C. OCH, CH(CH,)2 Q CH,
(d)
CHg
c) (d)
46. In the given reaction sequence, identify (B)
anhy.AlCl3
A, (A) CH3
CçH,+Cl CH,O-CH,
(Excess)
Cl. CH,
NBS/hv ’(B)
49. Nitration of the compound CH
(a)
H,C¡
gives
Br
Br, NO,
(b) O - O -CH, (a) CH3
Br H,C
NO,
(c) CçHs-CH, CH C6H,
(b) CH3
(d) Br -CiH,O-c-O -Br
H,C¡

47. The final product of the given reaction is

CH, (c) CHg
KMnO4X]
’[X][Y]
H
Bry
Fe H,Co
(Small quantity) NO,
CH, COOH
(d) CH3
C
(a) b H,C
Br
Br
Reaction Mechanism 493
OH
OH
CH,
50. HNO3
H ’ (a) (b)
Major product is :
OH
NO, NO,
(a
(b)
CH,
NO2
53.
Fe/HCI ’(A) HNO3 ,(B).The major product
HSO 4
(c)
-NO, (0) (b) is :
N=0
NO2 (a) (b) NH
51. Product of the reaction is NO,
NH,

¢oOH. HÐ
H0 Product NO, H H

54. In the given reaction

CH, H-CH, -CH, CH,aAIl3,(X)

(a) HO -CH, Zn-Hg/HCl ,(Y): The final product (Y) is :

(a) (b)
HC
H,C

(c) -OH +
CH,
CH HC
(C (d)

55. Give the major product from the following reaction

sequence
OH
Br2 H
FeBr, H,SO, AICl, H,o Major product
CH3 H Br
52, +[A]: [A] is Br

(b)
CHg
SO,H
|494) NCERT Chemistry
Br Br
Booster-X
(c)
(d)
(c) (d)
SO,H
C Cl
56. In the sulphonation, acetylation and formylation of
60. What could be the product the following1
for
benzene the group of effective electrophiles would
be:
OCH,
() AlCl3
() HO
reactiong
(a) So,CH ,C=0,HCO
(b) SO3,CH,C= 0,HCO
(c) SO3, CH ,CHO,CO + HCI OCH, 0
(d) HSO3,CH CO, HCO
57. Most reactive towards nitration is :
D
D OMe
(a) Me OCH,
D
D
D
(b)
Me
OMe
(C) (d)
D
D

58. What could be the product for the following reaction? (c)
(1) Alcl3 OCH,
() HO Products ?
(d)
MeO
(a) (b)

61. What could be the product for the following reacion?

OH N(CH )2 NaNO 2, HCI
’Product ?
(c) (d) |
CI N,
59. What could be the product for the following reaction? (a)

CH,
Zn(Hg) HCI, heating Major product ? N
N(CH3)2 NO
OH (c)
CH,
OH N
62. What is the correct order of decreasing reactvuy
(a) (b) (fastest to slowest) toward electrophilic aromatt
substitution for the following compounds ?
OH
OH
 peaction Mechanism
495
Co,H CH,
(i)
Br, C Zn(H8),
(a) || AlC, HCI
(i)
OCH3 PeBr,

(iv)
Zn (Hg),
(a) i> ii> iii> iv
(b) ii>i>iv>ii
(b) AlCl, Br2
FeBra HCI
(c) ii >ii >iv >i
(d) iv > ii >ii> i
63. Which of the following reaction sequences would be
the best for CI Zn (Hg) Br2
synthesizing
propylbenzene ? the compound,
1-bromo-3
AICl, HCI FeBr3
Br.
Brz
AICl, FeBr3
1-Bromo-3-propylbenzene

Answers

(c) 4. (d) 5. (a) 6. (a) 7. (c) 8. (d) 9. (a) 10. (a)

1. c) 2. C) 3.
13. (b) 14. (b) 15. (c) 16. (b) 17. (b) 18. (c) 19. (d) 20. (b)
11. c 12. (a)
25. (b) 26. (C 27. (C) 28. () 29. (d) 30. (b)
21. C) 22. () 23. C) 24. (b)
35. (b) 36. (C) 37. (a) 38. (b) 39. (d) 40. (b)
31. (C 32. (c) 33. (b) 34. (c)
44. (b) 45. (c) 46. (c) 47. (b) 48. (a) 49. (c) 50. (c)
41, b) 42. 43. (b)
54. (b) 55. (c) 56. (b) 57. (a) 58. (b) 59. (c) 60. (d)
51. b) 52. () 53. (b)
61. (c) 62. C) 63. (b)