Answers: Exercise-I

AROMATIC COMPOUNDS Page # 45
Answers
Exercise-I
1. A 2. D 3. B 4. B 5.D 6. D 7. D
8. B 9. B 10. A 11. A 12. C 13. B 14. B
15. B 16. C 17. B 18. A 19. D 20. D 21. B
22. C 23. B 24. B 25. A 26. D 27. C 28. D
29. B 30. B 31. D 32. C 33. A 34. B 35. D
36. A 37. D 38. A 39. B 40. B 41. A 42. B
43. B 44. B 45. D 46. B 47. C 48. C 49. D
50. C 51. D 52. A 53. D 54. C 55. D 56. D
57. A 58. B 59. A 60. A 61. C 62. B 63. B
64. B 65. D 66. A 67. C 68. A 69. D 70. C
71. A 72. B 73. B 74. A 75. C 76. D 77. A
78. A 79. C 80. C 81. A 82. D 83. C 84. B
85. D 86. C 87. C 88. A 89. B 90. A 91. A
92. C 93. C 94. A 95. D 96. D 97. D 98. B
99. B 100. B 101. A 102. C 103. B 104. A 105. B
106. B
Exercise-II
1. A,B,C,D 2. A,C 3. A,B,D 4. A,B,C,D 5. A,B 6. A,B,C

7. A,B,C 8. A,B,D 9. A,B 10. A 11. C,D 12. B
13. C 14. C 15. B,C,D 16. B 17. B,D 18. C,D
394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
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Page # 46 AROMATIC COMPOUNDSE
Exercise-III
1. 2.
O
CH(Me)2
3. (A) (B)
Ph Ph
Cl
Cl
4. (i) + AlCl
 3  (ii) + AlCl
 3 
5.
OCH3
OCH3
6. (1) + (b)
7. o , p - directing
CF3
8. (A) (o/p) Br NH (B) (meta)
Br
C(Me)3
N+(Me)3
(C) (meta) (D)
Br(o/p)
Br

O
(E)
Br(o/p)
9. Due to effecive delocalization of 2p-2p in comparison to 2p-3p, that’s why anisole is more reactive
towards nitration.
Mix
10. – NMe2 group is + M effecting group 11. Benzene
AlCl3 HNO3+H 2SO4
12. (a) No reaction. (b) NO2(o/p) (c) SO 3H(o/p)
(d) (o/p) (e) Me(o/p) (f) Br(o/p)
NO2 NO2
13. (1) (B) (C) No reaction
Cl NO2
14.
C6H5CH2S H2NNH CF3
NO2 NO2
15. (i) (ii) (iii) (iv)

O2N
CH3 NO2 OCH3
Cl Br
Br OCH3
(v)
CH 2SCH 3
OCH2CH3 SCH2C6H5
NO2 NO2
(vi) (vii)
NO2 NO2
16. (a) CH2 CH 2 (b)
(c)
OMe
+
Br NO2
(d) (e) Fe+2 (f)

NO2
(o,p)
+ SO3H
OH OH
Br Br OH
Br
17. and
Br Br
Cl
Cl
18. and
Cl
(1) (B)
Exercise - IV (Matrix)
1. A  P , R ; B  P, R ; C  P , R ; D  P , S
2. A  Q , S ; B  P , R ; C  R ; D  P
3. A  P ,R ; B  P , R ; C  P , R ; D  P , R
4. A  P ,R ,S ; B  P , R ; C  Q ,S D  Q, R, S
5. A P ; B  Q ; C  R ; D  S
6. A  Q;B  P  ;C  Q;D  Q
7. A  P,Q ; B  Q , S ; C  P ; D  R
8. A  P ; B  P, ; C  Q, ; D  R , S
9. A  P, R B  P, R, S ; C  Q, R ; D  P , R
10. A  P , S ; B  P, R, ; C  P ,Q ;  D,,  T
11. C 12. D 13. C
Exercise-V
1. C 2. D 3. D 4. A 5. D 6. B 7. A
8. D 9. C 10. A 11. C 12. A 13. B 14. B
15. D 16 A 17. D 18 D 19. C 20. B 21. D
22. C 23. C 24. C 25. C 26. B 27. B 28. D
29. C 30.D 31. C 32. C 33. A,B 34. B,D 35. B,C,D
36. A,C 37. A,C
Exercise-VI
NO2 NH2
1. HNO
3  Sn

H 2SO 4 HCl
2. Pi - bonds of benzene are involved in aromaticity, not open for electrophilic addition reaction. Rather, it
undergo electorphilic substitution reaction.
3. CH3CH2OH + PCl5  POCl3 + HCl + CH3CH2Cl

C6H6 + CH3 CH2Cl AlCl
 3  C6H5 – CH2CH3
Friedel - Crafts reaction
H H
4. It has 12 sigma and 3 pi-bonds.

H H
NaNO 2 / HCl
5. C6H5 – NH2    C H N +Cl– CuCl
  C6H5 – Cl
O 6 5 2 heat
C – CH2CH3
6. + CH3CH2COCl  AlCl 3

Friedel - Crafts acylation
7. lntramolecular H - bonding in ortho nitrophenol lowers its boiling point.
O
H
+ O–
N
ortho nitrophenol
No such intramolecular H-bonding is possible with p-nitrophenol and rather it is associated together by
intermolecular H - bonding which increases the boiling point.
8. The compound must contain a hydroxy group on the ring with all three ortho/para positions vacant :
OH
OH
Br Br
+ Br2 water
CH3
CH3
Br
9. Phenol is weaker acid than carbonic acid.
10
OH OH
CHO

H
+ CHCl3 + NaOH 
H 2O
Reimer Tiemann’s reaction
11. (i) Lime is heated with coke at high temperature and then hydrolysed to form acetylene. This acetylene
on passing red hot tube polymerises to form benzene:
CaO + 3C 2000
 C
 CaC2 + CO 
Lime Coke
CaC2 + 2H2O  Ca (OH)2 + C2H2
acetylene
Cu
3C2H2  C6H6

benzene
(ii) – CH3 in toluene is ortho/para directing group first oxidised to – cooH in order to make it meta
directing and then nitrated.
CH3 COOH COOH
K
2 CrO 7
 Conc
 .HNO 3

Conc .H 2SO 4
NO2
12. Both – CH3 and – OCH3 are activating groups but chloro is deactivating group in electrophilic aromatic
substitution reaction.
Also – OCH3 activative more than – CH3 due to resonance effect by the former group. Therefore the
overall order of reactivity is :
Chlorobenzene < benzene < toluene < methoxy benzene
NH2 NH2
Br Br
NaNO 2
13. Fe
+ Br2(excess)   
HCl/0 C
NO2 NO2
N2Cl–
+
Br
Br Br Br Br
CuBr
 Sn
– HCl

NO2 NO2
Br
Br Br Br
Br Br
NaNO 2

HCl H
3 PO 2

NO2
+ –
14.
+ –
The above resonance activate an aromatic ring for electrophilic substitutuion reaction.
15. C6H5 – CH (OAc)2
CH 3 CH(OAc) 2 CHO
CrO
3  H
2O
 
( CH 3CO ) 2 O H
Intermediate
C(CH 3) 3
16.
Br
Br
17. Fe
+ Br2  HNO
3 
H 2SO 4
NO2
18.
C–O HNO
 3 / H 2SO 4
 C–O NO2
mononitration
deactivated ring activated ring
+
+ C
19. R– C  O R– =O
I II
I is more stable resonance structure of acylium ion than II on the following grounds.
(i) it has more convalent bonds.
(ii) It has complete octet of both carbon and oxygen.
CH3
C – CH3
20. (i) + (CH3)2 CHCH2OH  H 2SO 4
CH3
CN
CH2CH3
CH – CH3
i ) Br2 / heat
(ii) ( 
( ii ) NaCN
21.
CH3 CH 3 CHO
AlCl3 CrO3 H
+CH 3Cl (CH 3CO)2O
NO2 NO2
NO2 NH2 CN
22. Zn
HCl
 NaNO
2  CuCN

HCl / 0 C
COOH CONH2
HH
2O

 NH
3 

benzamide
O

23. NH – C – CH3
H
 NH3 NaNO
2  N2Cl–
H 2O HCl / 0 C
NO2
NO2
NaNO
 2 ( aq )
 I2

heat Fe
I I
NH3 N2Cl–
NO2 NO2
(i ) NaNO 2 / HCl
24. 
0 C
 Anisole

NO2 NO2
N=N OCH3
O2N NO2
25. In presence of FeBr3, Br2 produces Br+(an electrophile) which attacks the benzene ring at o - p position
to give p- bromotoluene. In presence of light side chain is attacked to produce benzyl bromide.
OCH3
OCH 3
OCH3
O (i) AlCl3
26. +  
Zn
( Hg
) 
(ii) H 3O HCl
O COOH COOH
Fridel - Crafts
reaction
(1) (B)
NO2 NO2
Br2
27. + conc HNO3 / conc H2SO4  
Fe
Br
.. +
NH2 N2Cl– I
SnCl
2  NaNO
2  KI
(aq )

HCl HCl / 0 C CuI
Br Br Br
m - bromoiodo
benzene
CH 3
CH3 CH3
CH 3 – C – CH 2Br
28. + AlCl
 3 
CH3 – C – CH 3
CH3
CH3
O O O
NH – C – CH3 NH – C – CH3 NH – C – CH3

Br2
29.  +
Fe
Br Br
Et
COOH
O 
30. (a)  Soda
 lim e

Cl CN COOH
CH2CH3
CH – CH3 CHCH3 CHCH 3
Cl 2
(b) 
hv KCN
 HOH

31. C6H5CH = CHC6H5

(Cis and trans forms )
32. Nitro group is a very strong deactivating group the very slow Friedel- Crafts reaction does not takes
place in presence of nitro groop.
NHCOCH3 NHCOCH3 NHCOCH 3
33. Br / Fe
2   +
Br Br
34. lntramolecular H - bonding in ortho hydroxy benzaldehyde is responsible for decrease in melting and
boiling points.
O
H
H
intramolecular
H - bonding
p- hydroxy benzaldhehyde molecules are associated by intermolecular H-bonds has higher metting and
boilling points.
F OCH3
35. CH
3ONa

 + NaF
heat
NO2 NO2
Nucleophilic aromatic substitution occur which is assisted by electron withdrawing – NO2 group from para
position.
36. C6H5NH2 NaNO

2  C6H5N+2Cl– CuCN C6H5CN LIAlH
4  C6H5 – CH2NH2
HCl /  C or H 2 . Ni
N Br2
37.  N Br
Fe
(activated)
(deactivated)
CH3
C – CH 3
38. (i) + KMnO4 No oxidation takes place
CH3
tert butyl benzene

(no. a – H)
(ii) Pi - electrons of double bonds are involved in aromatic delocalisation (aromaticity). However
electrophilic addition do not ocour as it would distroy aromatic stability however electrophilic substitution do
not destroy asomaticity
OMe
Br ONa OMe
NaOH

39. high Pr essure
( Benzyne mech )
MeSO4
(SN2) conc
 . H 2SO 4
 NaOH

SO3H
OMe OMe

H
3O

ONa OH
Alternative rout
Br Br Br
Br
conc
 .H 2SO 4
 NaOH
 

Me 2SO 4
SO3H ONa OMe
OMe OMe
NaOH
 
 high Pr essure H

3O

ONa OH
C
C CH2CH2CH3
CH 2CH 2CH 3 Cl 2
40. 
FeCl 3
Cl
Cl
Cl
NO2
CH 2CH2CH 2CH 3
CH2CH2CH2CH3
A Na
Hg
 Cl HNO
3 
HCl H 2SO 4
Cl
Cl
Cl
NO2 NO2
H
2 C  CH – CH 2 ONa
  Cl H
2 / Pd / C
 Cl
O – CH2 – CH = CH2 O – CH2CH2CH3
OH O– OH
–
COO COOH
NaOH H
41. (i) CO2 
Kolbe’s reaction
OCOCH3
COOH
CH CO  O
3 
2

heat
aspirin
COOH COOH COOH
(ii) HNO
3  Sn
/ HCl
 NaNO
 2  HCl

H 2SO 4 HBF4 
NO2 NH2
COOH
F
meta - fluorobenzoic acid
42.
+ –
COOH COOH HOOC NH3Cl(aq)
aq. HCl
+
OH NH 2 HO COOH
(ether layer)
dissolve in diethyl ether
COOH COOH NC
aq. FeCl3 violet + CHCl3

colouration +KOH
OH NH2 COOK
foul smell
43. II is more acidic due to – I effect of F.
NO2 NO2
HNO3 NH4HS
44. H2SO4
heat NO2
NO2 NO2 NO2
NaNO2 NaOH
HCl/0ºC H2O
—
NH2heat N2Cl OH
Fill in the Blanks
45. Aniline 46. Phenoxide ion 47. Nucleophilic 48. Phenoxide ion
49. Ortho-nitrophenol 50. Zwitter ionic

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AROMATIC COMPOUNDS Page # 45

1. A,B,C,D 2. A,C 3. A,B,D 4. A,B,C,D 5. A,B 6. A,B,C

12. (a) No reaction. (b) NO2(o/p) (c) SO 3H(o/p)

(d) (o/p) (e) Me(o/p) (f) Br(o/p)

13. (1) (B) (C) No reaction

C6H5CH2S H2NNH CF3

15. (i) (ii) (iii) (iv)

CH3 NO2 OCH3

16. (a) CH2 CH 2 (b)

(d) (e) Fe+2 (f)

11. C 12. D 13. C

3. CH3CH2OH + PCl5  POCl3 + HCl + CH3CH2Cl

4. It has 12 sigma and 3 pi-bonds.

Friedel - Crafts acylation

7. lntramolecular H - bonding in ortho nitrophenol lowers its boiling point.

9. Phenol is weaker acid than carbonic acid.

Reimer Tiemann’s reaction

CH3 COOH COOH

15. C6H5 – CH (OAc)2

NH – C – CH3 NH – C – CH3 NH – C – CH3

31. C6H5CH = CHC6H5

NHCOCH3 NHCOCH3 NHCOCH 3

36. C6H5NH2 NaNO

tert butyl benzene

SO3H ONa OMe

 high Pr essure H

O – CH2 – CH = CH2 O – CH2CH2CH3

COOH COOH COOH

dissolve in diethyl ether

aq. FeCl3 violet + CHCl3

43. II is more acidic due to – I effect of F.

NO2 NO2 NO2

Fill in the Blanks

49. Ortho-nitrophenol 50. Zwitter ionic

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