Nitrogen Containing Compounds 1393

Assertion & Reason 4. (b) CH 3  CO  NH 2  2 NaOH / Br

 CH 3  NH 2
Hofmann' s bromamide (1c)
(2c)
1 a 2 a 3 b 4 d 5 b Na  C 2 H 5 OH
5. (b) CH 3 C  N  4[H ]    CH 3 CH 2 NH 2
6 c 7 a 8 c 9 c 10 b Reduction

11 c 12 b 13 e 14 c 15 a
6. (b) CH 3  CH 2  CO  NH 2  Br2  4 KOH 
Propionami de
16 a 17 d 18 b 19 d 20 d CH 3 CH 2 NH 2  K 2 CO 3  2 KBr  2 H 2 O
21 a 7. (c) C 2 H 5 I  NH 3  HI  C 2 H 5  NH 2
C 2 H 5 OH  NH 3  H 2 O  C 2 H 5  NH 2

9. (c) CH 3  CH 2  NO 2  6 [H ]  
Sn / HCl

Nitro ethane

CH 3  CH 2  NH 2  2 H 2O
Ethyl amine

NH CH I
11. (d) CH 3 I 
3
 CH 3 NH 2 
3
 (CH 3 )2 NH
 Methyl amine Dimethyl amine
Introduction of Nitrogen Containing Compounds CH 3 I

 (CH 3 )3 N
Trimetyhlamine
4. (d) C 3 H 9 N can form all the 3 amines. NH 2 NH  CO  CH 3
CH 3 CH 2 CH 2  NH 2 , CH 3  CH 2  NH  CH 3
CH 3  CO
O
o o
1 amine 2 amine 12. (d) + + CH 3 COOH
CH 3  CO
CH 3  N  CH 3 Aceticanhydride Acetanilide
|
Aniline
CH 3
o
3 amine 
16. (c) CH 3  N  C  4 [H ]    CH 3  NH  CH 3
Reduction
5. (c) (CH 3 ) 2 C  O  H .CH 2  COCH 3  NH 3 o
2 amine

(CH 3 )2 C CH 2 COCH 3 17. (a) CH 3 NO 2  3Cl 2  3 NaOH 
| Nitromethane
NH 2
diacetonea mine CCl 3  NO 2  3 NaCl  3 H 2 O.
 (chloropicrin)
8. (d) Allyl isocyanide. CH 2  CH  CH 2  N  C Reduction
18. (b) R  CH 2  NH 2
9. (c) NH 2 [H] 1 o amine
NH 2
1o
R C  N
Nitrile
Hydrolysis
NH 2 R  COOH  NH 3
o  acid
1 amine H3O
19. (a) C 2 H 5 OH  NH 3  C 2 H 5 NH 2  H 2 O .
alumina
12. (b) CH 3 CH 2  O  N  O is a nitrite derivative, hence it

is not a nitro derivative. H O/H
20. (c) R  CN  H 2 O 2 RCOOH  NH 3
13. (b) CH 3 CN is called acetonitrile....
It yield amine when reduced as –
15. (b) Four 1 o amines are possible R  CN  H 2  R  CH 2  NH 2
CH 3 CH 2 CH 2 CH 2 NH 2 , (CH 3 )2 CHCH 2 NH 2 ,
PO
CH 3 CH (NH 2 )CH 2 CH 3 , (CH 3 )3 CNH 2 21. (b) CH 3 CONH 2  CH 3 CN 
2 5
 CH 3 CH 2 NH 2
4H

O
||
Preparation of Nitrogen Containing Compounds 22. (a) CH 3  CH 2  N  O  3 H 2  CH 3 CH 2 NH 2  2 H 2 O .

1. (c) Hofmann’s bromamide reaction 23. (a) CH 3 NH 2 

2 NO
 CH 3 OH  N 2  H 2 O
CH 3  CO  NH 2  Br2  4 KOH  H 2O Methyl amine

Acetamide 24. (a) R  NH 2  CHCl 3  3 KOH  R  NC  3 KCl  3 HO

CH 3 NH 2  K 2 CO 3  2 KBr  2 H 2 O 1 o  amine
Methyl amine
NH 2 N 2Cl
2. (d) CH 3 CONH 2   CH 3 NH 2 .
NaOBr

3. (b) CH 3 CONH 2  Br2  4 NaOH  25. (b)

NaNO
2

/ HCl
+ 2 H 2O .
Acetamide o o
0 5 C
CH 3 NH 2  Na 2 CO 3  2 NaBr  2 H 2 O Aniline Benzene diazonium chloride
Methyl amine
 1394 Nitrogen Containing Compounds
SOCl 51. (c) Secondary amines gives oily nitrosomine with nitrous
26. (b) CH 3 CH 2 COOH 
2
 CH 3 CH 2 COCl  SO 2  HCl acid.
CH 3 CH 2 COCl  NH 3  CH 3 CH 2 CONH 2  HCl (CH 3 CH 2 )2 NH  HONO  (CH 3 CH 2 )2 N . NO  H 2 O
oily
CH 3 CH 2 CONH 2  Br2 / NaOH  CH 3 CH 2 NH 2  CO 2
Ethyl amine 52. (a) When aniline is treated with HNO 2 at 0–5°C then
PCl5 NH 3 diazonium salt is formed and by the coupling of
27. (c) CH 3 COOH  CH 3 COCl  CH 3 CONH 2
diazonium salt and phenol azo dyes are prepared.
  CH 3 NH 2
NaOBr
NH 2 N   NCl 
NH 2 NH 2 N 2 Cl
Br Br Br Br NaNO 2  HCl
   
Br2 NaNO 2 0 5 C
28. (d) 
 
HCl
Aniline Benzene
Br Br diazonium chloride
Br Br
 
Boiling
OH
C 2 H 5 OH
N   NCl 

Br
29.
LiAlH4
(c) CH 3  N  C   CH 3  NH  CH 3 +  
coupling

sec. amine weakly alkaline,OH 

Phenol
Na  ROH
32. (a) CH 3 CONH 2    CH 3 CH 2 OH  H 2 O

NH 2 N C HO N N
N
Azo dye
33. (a)  CHCl 3  3 KOH   3 KCl  3 H 2 O . 54. (a) p-nitrobenzene from p-nitroaniline.

35. (c) Methyl amine is the strongest base. NO2 NO2 NO2
pt / H
36. (c) C6 H 5 NO 2  6 H 
2
 C6 H 5 NH 2  2 H 2 O
Nitrobenzene Aniline
 o 
NaNO 2


KI
HCl , 0  5 C
38. (a) C2 H 5 NH 2  CS 2  HgCl2  C2 H 5 NCS  2 HCl  HgS .
NH2 N2+Cl– I
39.
NaNO 3
(d) C6 H 5 NH 2  C6 H 5 N 2 Cl 
H 2O p-nitroiodobenzene
HCl p-nitroaniline
C6 H 5 OH  N 2  HCl 55. (b) C 2 H 5 Br  KCN   C 2 H 5 CN  KBr
alcohol

H O
41. (d) 2C6 H 5 Cl  2 NH 3 2

chlorobenzene in xylene 570 o K
Properties of Nitrogen Containing Compounds
C6 H 5 NH 2  Cu 2 Cl 2  H 2 O
(Aniline)

44. (c) C6 H 5 NH 2  HCl  NaNO 2  C6 H 5 N 2Cl 1. (d) Tertiary amine does not react with nitrous acid
Sn  HCl
because in it -H atom is absent.
46. (b) C6 H 5 NO 2  6 H   C6 H 5  NH 2  2 H 2 O 2. (d) Due to +ve I.E. of alkyl group, N-atom of amines
NaNO 2  HCl 0 C
o acquires patrial –ve charge and thus electron pair is
47. (b) C6 H 5 NH 2 
 C6 H 5 N 2 Cl easily donated.
Sn 3. (b) CH 3  C H  COOH
48. (a) CH 3 NO 2  6 H 
 CH 3 NH 2  2 H 2 O |
HCl
NH 2
 C6 H 5 N 2 Cl  
NaNO / HCl HNO
49. (c) C6 H 5 NH 2 2 
2
 The compounds in which both amino ( NH 2 ) as well
o o
0 C 5 C (X) H 2O
as acidic (–COOH) group is present is called amino
C6 H 5 NO 2  N 2  HCl acid.
(Y)
4. (b)
  
50. (a) Halogen have –I and +M effect by which its electron
delocalized in benzene ring by resonance & due to its ON O O  N  O : O  N  O : O  N  O :
  
–I effect its bonded with benzene ring and cannot be +
+
substitute by CN  & show the inertness against
KCN while other option gives Aromatic nitrile +
ArN2  CuCN  ArCN  N 2  Cu  Presence of  NO 2 group decreases electron density
at o- and p- positions. Hence, incoming electrophile
ArCONH 2   ArCN
P2 O5
goes to m position. Therefore it is m-directing group.
 H 2O

ArCONH 2  SOCl 2  ArCN  SO 2  2 HCl 6. (c) R  C  N  2 H 2 O    R  COOH  NH 3

Hydrolysis

NH 2 N  NCl

Benzene diazonium
Aniline
chloride
 Nitrogen Containing Compounds 1395
CH NH
23. (b) Red 
3

2
 Blue
0o C (Litmus paper)
7. (c) + HNO 2  HCl  + 2 H 2O
Diazotization This litmus paper test shows basic nature of amine.
24. (c) Presence of alkyl group increases electron density on
nitrogen atom due to +I effect. Thus basic nature
increases.
9. (b) R  C  N  R  Mg  X  R  C  N  Mg  Br 25. (a) Mustard oil reaction
Alkylcyanide |
HgCl
R CH 3  CH 2  NH 2  CS 2 
2

Hydrolysis Ethyl amine

Br CH 3  CH 2  N  C  S  H 2 S
R  CO  R  NH 3  Mg Ethyl isothiocyanate
Ketone OH
NO 2 NO 2

10. (c) + 3 NHO 3  + 3 H 2O 28. (c)  

Nitration
fuming
NO 2 NO 2 NO 2 NO 2
sym-trinitro benzene 1, 3, 5-trinitrobenzene
KMnO
11. (c) CH 3  CH 2  NH 2 
4
 CH 3  CH  NH 3- nitro group can be introduced.
Ethylamine [O ] Aldimine
HNO
 34. (a) R  CH 2  NO 2 
2
 R  C  NO 2
H 3O

 CH 3  CHO o ||
1 nitro
Acetaldehyde N  OH
Nitroloic acid
12. (b) Only primary aromatic amines can undergo
diazotisation.   R  C  NO 2
NaOH

(b) R  CH 2  NH 2  O  CH  R 
||
13.
o
aldehyde N  O  Na 
1 amine (Blood red)
R  CH 2  N  CH  R  H 2O HNO 2
Aldimine 35. (b) (R)2 CH  NO 2 
(R)2 C  NO 2
|
14. (c) CH 3  CO  NH 2  HNO 2  CH 3 COOH  N 2   H 2O N O
Acetamide Acetic acid

  Blue colour.

NaOH

NO2 NO2 PO
37. (b) CH 3 CONH 2  CH 3  C  N  H 2 O .
2 5
conc. H 2 SO 4
15. (c) + HNO 3 
 Acetamide Acetonitrile
conc. NO2 38. (b) CHCl 3  C2 H 5 NH 2  3 KOH 
Nitrobenzene m-dinitrobenzene 
C2 H 5 N  C  3 KCl  3 H 2 O
 NO 2 group is meta directing group. Ethyl isocyanide

39. (d) CH 3  C  N  2 H 2 O  CH 3 COOH  NH 3

16. (a) R  O  N  O  6 [H ]   ROH  NH 3  H 2 O
Sn / HCl
Methyl cyanide Aceticacid
Alkyl nitrite Alcohol
40. (c) CH 3 CONH 2  Br2  4 KOH 
17. (d) CH 3  CH 2  NH 2  HCl  CH 3 CH 2  NH 3 Cl  (2c )
Ethyl ammonium chloride
Amines are basic in nature they react with acid to form CH 3 NH 2  K 2 CO 3  3 KBr  2 H 2 O
(1c)
salt.
 41. (a) (C2 H 5 )2 NH  (aq.) HONO  (C2 H 5 )2 N  N  O  H 2 O
18. (a) (CH 3 ) 2 NH  CH 3 NH 2  (CH 3 ) 3 N  N H 3 Diethyl nitrosoami ne
2 o amine is 1 o amine o Ammonia is Na  EtOH
most basic
3 amine least basic 42. (c) CH 3  C  N    CH 3  CH 2  NH 2
Reduction

NH 2 N C HNO 2 K Cr O7

 CH 3 CH 2  OH 2 2 
 CH 3 COOH
H 2 SO 4
19. (b) + CHCl 3  3 KOH  + 3 KCl  3 H 2O
HNO PCl
Phenyl isocyanide 43. (b) C 2 H 5 NH 2 
2
 C 2 H 5 OH 
5
 C 2 H 5 Cl
Aniline Ethyl amine Ethyl alcohol
20. (c) Because in tertiary nitroalkanes   H atom is
NH
absent. 
3
 C 2 H 5 NH 2
Ethyl amine
21. (a) Primary amine reacts with CHCl 3 and alc. KOH to
44. (c) CH 3 CH 2  NH 2  HNO 2  CH 3 CH 2  OH  N 2  H 2 O
form isocyanide while secondary and tertiary amines 1
o Alcohol

do not react.
(CH 3 CH 2 )2 NH  HNO 2  (CH 3 CH 2 )2 N  N  O  H 2O
22. (d) Friedel-craft’s reaction is used for the preparation of 2o Nitroso amine
alkyl benzene or acetophenone. It is not a method to 
45. (d) RN  C  2 H 2 O    RNH 2  HCOOH
Hydrolysis
prepare amine. Alkyl Isocyanide o
1 amine
Formic acid
 1396 Nitrogen Containing Compounds
46. (d) CH 3 NH 2  2 HNO 2  CH 3  O  N  O  N 2  2 H 2 O 63. (c) 3 o amine cannot be Acetylated because replacable H-
2CH 3 NH 2  2 HNO 2  CH 3  O  CH 3  2 N 2  3 H 2 O atom is absent.
67. (e) Because
NO 2 NO NHOH N-N dimethyl propanimine
CH 3
47. (d) 
2H

2H |

Zn / NH 4 Cl 2 Zn / NH 4 Cl
CH 3  N  CH 2  CH 2  CH 3
3 o amine
Phenyl hydroxyl amine
NH  CH 3
50. (b) Because the N atom in aniline has a lone pair to
donate and also due to +I effect of  NH 2 group. N-Methyl aniline 
NH 2 o
NH 2 aniline  1 o amine.
2 amine
Br Br
51. (d) + Bromine water  68. (c) Replacable H  is absent.
excess
NO 2 NO NHOH
Br

52. (d) R  NH 2  CHCl 3  3 NaOH  RN  C  3 NaCl  3 H 2O
69. (a)  
Zn / HCl

2H

The unpleasant smell is due to the formation of

Nitro benzene N-phenyl
isocyanide. Nitro benzene
hydroxylamine
53. (c) RNH 2  NaNO 2  HCl  R  OH  NaCl  N 2  H 2 O O
NH 2 Because oxidation of
NH 2 NHCH 3 aniline occur in
70. (c) 
3

HNO absence of making
54. (c) + CH 3  Cl  + CH 3 Cl . effect.
O
P - Benzoquinone
N (CH 3 )2 NO2 NO2 NO2
N  (CH 3 )3
Cl 
72. (c)  
NaNH 2
 
NH 3
+ CHCl 3  
 Br

3, 4-aryne
Quaternary ammonium salt Br NH2
NH 2 73. (a) R 2 NH  RNH 2  R 3 N  NH 3 .

55. (c) + HNO 3 / H 2 SO 4 A black mass. NO2 NH 2

Nitration of aniline without protecting the amino 75. (b) + NH 4 HS 

group is not possible because HNO 3 is a strong NO 2 NO 2
oxidising agent which oxidises aniline. 76. (a) Because of presence of electron withdrawing group -
CH 3  
56. (d) NH and CH 3  NH 2 . NO 2 .
CH 3 77. (a) To supress the concentration of the aniline available
In methyl amine only one electron releasing group is for coupling other rise coupling occurs.
present but in dimethyl amine two electron releasing 78. (b) R  NH 2  HNO 2  R  OH  N 2  H 2 O .
groups are present which increase the basicity higher alcohol

in dienethyl amine. 79. (c) C6 H5 NH 2  (CH 3 )3 N  CH 3 NH 2  (CH 3 )2 NH

57. (d) Nitro compounds are not explosive but stable H O/H


compound. 80. (b) CH 3 CN  CH 3 MgI  (CH 3 ) 2 CNMgI 2

(A)  NH 3
58. (c) CH 3  NH 2  HNO 2  CH 3 OH  N 2  H 2 O
OH
60. (c) R 3 N  HONO  R 3 N . HONO called as Quaternary CH 3 COCH 3  Mg
(B) I
ammonium salt.
NO2 N 2Cl 82. (d) C 6 H 5  NO 2 
 C 6 H 5 NH  NHC 6 H 5  4 H 2 O
10 [ H ]
Zn / NaOH Hydrazo benzene

4 NO 2 Me 
61. (b) 
 83. (a) RCOCl  2 Me 2 NH  RCON  Me 2  N H 2 Cl 
cold Me
4 NO Me = Methyl.
But R  NH 2 
2
 R  OH  N 2  H 2 O 86. (b) Phenol react with aniline to give diazonium salt by
cold


coupling but Methyl amine not react with phenol.
H O/H
62. (a) CH 3 CN 2
 CH 3 COOH  NH 3 87. (b) C6 H 5 SO 2 Cl is called Hinsberg’s reagent they react
with sec amine to form a product in soluble in
 Nitrogen Containing Compounds 1397
alkalies. This reaction used to separate 1 o , 2 o and
3 o amine from their mixture.
88. (b) A mixture of benzene and aniline can be separated by
dil. HCl.
NO2 NO2

89. (b)  HNO 3  

H 2 SO 4
H 2O
NO2
m-dinitrobenzene
NaNO 2  HCl
90. (b) C6 H 5 NH 2 
 C6 H 5 N 2 Cl   C6 H 5 CN
KCN
NH 2 NHCOCH 3 NHCOCH 3 NH 2
o
(A) 0 C (B) (C)
Aniline
H3O Ac O Br
Br
H
 Br
115. (d) 2 
2
 
Hydrolysis
CH 3 COOH
C 6 H 5 COOH
(D) CH 3
CH 3 CH 3 CH 3
91. (c) Methyl isocyanate is industrially prepared by the
action of methyl amine with phosgene. 119. (a) Basicity of amines increase with increase in number
HCl of CH 3 groups (or any group which cause +I
CH3NH2 + COCl2  [CH3NH – CO – Cl]
effect), due to increase in electron density on N atom.

 CH3 – N = C = O As a rule, the basicity of t-amine should be more than
 HCl methyl that of s-amine, but actually it is found to be lesser
92. (d) R  NC  2 Hisocyanate
2 O  RNH 2  HCOOH . than s-amines. This is due to stearic hinderence of
93. (d) CH 3  NC  2 H 2 O  CH 3 NH 2  HCOOH bulkier alkyl groups, which decreases the availability
of lone pair of electron on the N atom of the amino
95. (c) CH 3 NC  4 H  (CH 3 )2 NH .
LiAlH4
group. Hence the correct order of basicity is :
ether
(CH 3 )2 NH  (CH 3 )3 N  CH 3 NH 2
NH2 NH2
120. (b) Amines are basic in nature, hence form salts with
Br Br acid.
99. (b)  3Br2  
Aqueous
2 RNH 2  H 2 SO 4  [RNH 3 ]2 SO 42 
121. (b) We know that
Br
2, 4, 6 tribromo C6 H 5 NH 2  CHCl 3  3 KOH  C6 H 5 NC  3 KCl  3 H 2 O
O aniline Aniline Chloroform phenyl isocyanide
||
H 2  Ni Thus in this reaction phenyl isocyanide is produced.
102. (a) R  C  NH 2  R  CH 2  NH 2
this is called carbylamine reaction.
104. (b) CH 3 CN  2 H 2 O   CH 3 COOH  NH 3
HCl
122. (d) Isocyanides on hydrolysis forms primary amines not
106. (a) CH 3 CH 2 NH 2  CH 3 COClCH 3 CH 2 NHCOCH 3  HCl ammonia
N Ethyl acetanilide 123.(b) C6 H 5 CONH 2  Br2  KOH  C6 H 5 CONHBr  KBr  H 2 O
O
||
 KOH
CH 3 CH 3
107. (a) NH  CH 3 COOH  N  C  CH 3 K2CO 3  C6 H 5 NH 2  

2 KOH
 C6 H 5 NCO  KBr  H 2O
CH 3 CH 3
C6 H 5 NH 2  (CH 3 CO )2 O  CH 3 CONHC 6 H 5  CH 3 COOH
108. (d) Anilinium hydrogen chloride produces chloride ion Acetanilide
which gives white precipitate with AgNO 3 . In fact (antipyretic)
anilium chloride is a part of aniline. O
||
NO 2 NO 2 C  NH 2 CN
124. (d)
Conc. H SO  
POCl 3
 H 2O
109. (b) 
2

4
 
 SO 3 H
Benzonitrile
O
(A) ||
NH2 125. (d) (i) RCNH 2 + Br2 + KOH  RCONHBr
NO 2 NH-OH
+ KBr + H2O
110. (c) 
[H ]

[H ] (ii) RCONHBr + KOH  RNCO + KBr + H2O
Conc. H 2 SO 4 H 2 SO 4 (iii) RNCO + 2KOH  RNH2 + K2CO3
RCONH2 + Br2 + 4KOH  RNH2 + 2KBr + K2CO3
OH +2H2O
Nitrobenzene Phenyl hydroxyl p-amino phenol 126. (b) Aniline reacts with benzaldehyde and forms Schiff's
amine base (benzal aniline) or anils.

CH 3 C6 H 5  NH 2  O  CHC 6 H 5  C6 H 5 N  CHC 6 H 5
H 2O
H N
CH 3 Benzylidine aniline
113. (c) C6 H 5 CH  O 
CH 3
H N
CH 3

Anyhydrons
ZnCl 2

CH 3
N
CH 3
 1398 Nitrogen Containing Compounds
127. (d) CH 3 CONH 2  Br2  4 KOH  
2H O   CH 3 CHO
Boiling H 2 O
2
Acetamide Acetaldeyde
CH 3 NH 2  2 KBr  2 K 2 CO 3 CH 3
(Methyl amine)
138. (b) N
128. (b) N is most basic
| CH 3
H
 
139. (b) N-alkyl formamides when dehydrated with POCl3 in
130. (d) NH 2 N 2 Cl CN presence of pyridine give isocyanides.
140. (c) Pollutants which are formed by reaction amongst the
 
NaNO 2 primary pollutants (persist in the environment in the
2 

H / Ni
HCl  
CuCN
form they are passed into it) are called as secondary
DIAZOTISATION
A B pollutants. e.g. peroxyacyl nitrates (PAN) are formed
CH 2  NH 2 CH 2 OH through reaction between nitrogen oxides and
hydrocarbons in the presence of sunlight.
 
HNO 2 NH2 NH2 NH2 NH2
Nitrous acid
NO2
NO 2 NH 2 C D 141. (d)  
HNO 3
+ +
H 2 SO 4
NO2
131. (a) 
Weakly
acidic medium Aniline NO2
p-nitro aniline m-nitro o-nitro aniline
132. (d) C 6 H 5 NH 2 is least basic compound due to resonance aniline (47%) (2%)
(51%)
by which the Lone pair of nitrogen takes part in The reason for this is that, in acidic condition
resonance & due to unavailability of lone pair on N protonation of  NH 2 group gives anilinium ion
Aniline become less basic. The Lone pair of N is
delocalized into benzene ring by resonance ( NH 3 ) , which is of deactivating nature and of m-
.. + + + directive nature.
NH2 NH2 NH2 NH2
OH OH OH OH NH2 N2Cl
.–. .–.
142. (b) diazotizat
  
ion

NaNO 2  HCl / 0 5 o C
..
– Br Br Br Br
133. (b) Carbylamine (or isocyanides) give secondary amine
Br Br
on reduction. 3,4,5-Tribromoaniline
RN   C   R  NH  CH 3
Ni / H 2

3  
Carbylamine H PO
2
Secondary amine
134. (a) Azo dye is prepared by the coupling of phenol and Br Br
diazonium chloride.
Br
NH 2 N   NCl  143. (a) Basicity order is 1,2,3-Tribromobenzene

C4 H5 NH 2  (CH 3 )3 N  CH 3 NH 2  (CH 3 )2 NH
NaNO 2  HCl
    (CH 3 )3 N is less basic due to steric effect while
0 5 C
C4 H 5 NH 2 is less basic due to resonance.
Benzene
OH diazonium chloride
Tests for Nitrogen Containing Compounds
+ 
coupling
WeaklyalkalineMedium
1. (c) CH 3 CONH 2  Br2  4 NaOH 
Phenol Acetamide

CH 3 NH 2  Na 2 CO 3  2 NaBr  2 H 2 O
OH N N Methyl amine
N
p-hydroxyazobenzene NH 2
is a type of 1 o amine
C6 H 5 NH 2 2
 C6 H 5 N 2 Cl
NaNO / HCl
135. (b) CH 3 and hence gives +ve
(X )
5. (b) carbyl test
H 2O / H 

 C6 H 5 CN 
 C6 H 5  COOH
Cu 2 (CN ) 2

(Y ) Benzoic acid ( Z ) CH 3
Thus product Z is identified as C6 H 5  COOH
136. (c) This is Hofman-bromide reaction. In this reaction 6. (a) N =N NH 2
one carbon less amines are formed from amides.
Orange Colour
CH 3 CONH 2    CH 3 NH 2
Br2 / KOH
8. (a) Diazo-coupling is useful to prepare some dyes.
137. (c) CH 3 CN  2 H  HC  CH
HCl
Ether
N = N-Cl + H NH 2 
Benzenediazonium
chloride N=N NH 2
p-amino azo benzene (yellow dye)
 Nitrogen Containing Compounds 1399
9. (bc) (1) With NaHCO 3 

NH 3 Cl  NH 2
11. (a) CHCl 3 gives carbylamine test.
  NaHCO 3  + CO 2  NaCl  H 2 O
RNH 2  CHCl 3  3 KOH (alc.) 
Anilinium hydrochloride is an acid salt and liberates
RN C  3 KCl  3 H 2 O
alkyl isocyanide
CO 2 from NaHCO 3 .
But p-chloro aniline is basic not acidic it does not
Critical Thinking Questions liberate CO 2 .
NH 3 Cl 

1. (c) R1  H and R 2  R3  CH 3 (2) With AgNO3   AgNO3 

R1 H NH 3 NO 2  AgCl  (White ppt)

N  R3  N  CH 3
R2 CH 3 p-chloro aniline does not contain ionic chlorine to it
does not give white ppt with AgNO 3
Sec. amine reacts with Nitrous acid to form nitroso
amine yellow liquid. NO 2 NH 2

2. (c) CH 3 CH 2 NH 2  HNO 2  CH 3 CH 2 OH  N 2  H 2 O
Ethyl amine Ethyl alcohol 10. (a) + 6 [H ]  
Sn / HCl
+ 2 H 2O

NH 2 N 2 Cl Nitrobenzene Aniline
11. (a) C 6 H 5  NH 2  CHCl 3  3 KOH 
3. (a) 0 5C
 NaNO 2  2 HCl   C6 H 5 NC  3 KCl  3 H 2O
Phenyl Isocyanide

2 H 2 O  NaCl 12. (b) (CH 3 )2 NH  CH 3 NH 2  (CH 3 )3 N

K b  5.4  10 4 4.5  10 4 0.6  10 4
(CH 3 )2 N H  Cl  N  N  
HCl 13. (c) (CH 3 )2 NCOCH 3  HCl / H 2 O
dimethyl aniline 
(CH 3 )2 NH  CH 3 COOH
(CH 3 )2 N NN 14. (a) Order of basicity of amines
4. (c) Hofmann degradation of amide (i) 2 o  1o  3 o
(ii) R 2 NH  RNH 2  ArCH 2  NH 2  NH 3  ArNH  R 
R  CoNH 2  Br2  4 KOH 
ArNH 2  ArNH  Ar
R  NH 2  2 KBr  K 2 CO 3  2 H 2 O
primary amine NO 2 NO 2 NO 2
OH
NO 2 NH 2 15. (a)  KOH (solid)  
heat
+

5. (b)  
HNO 3 / H 2 SO 4
 
Sn / HCl
OH

Because OH  is nucleophile.
Nitrobenzene Aniline
16. (c) C6 H 5 SO 2 Cl  RNH 2  RNHSO 2 C6 H 5  
KOH

6. (b) The relative basic charecter of 1 o ,2 o and 3 o amines RNKSO 2 C6 H 5

also depends upon the nature of the alkyl group. soluble in KOH

R Relative basic strength 17. (b) When sulphur and nitrogen both are present in
organic compound during Lassaigne's Test, both
CH 3 R 2 NH  R  NH 2  R3 N  NH 3 changes into "sodium thiocyanate". (NaSCN) which
C 2 H 5 R 2 NH  R  NH 2  NH 3  R3 N gives a blood red colouration with Ferric ion.
3 NaCNS  FeCl 3  Fe(CNS )3  3 NaCl
CHMe 2 R  NH 2  NH 3  R 2 NH  R3 N Ferric sulpho cyanide
(Blood red colour)
CMe 3 NH 3  R  NH 2  R 2 NH  R3 N
H
7. (b) The nitrogroup is very firmly linked to the benzene does not have aromaticity by which the Lone
nucleus and does not undergo any displacement pair of electron of Nitrogen does not
18. (c)
reaction. Nitro group deactivates the benzene delocalised in benzene ring so it will be strong
nucleus. N base on other hand rest 3 have aromaticity i.e.,
| they follow the huckel rule so the electron pair
NH 2 N=CH–CH3 H of Nitrogen delocalised in ring by resonance &
resulting they become less basic.
8. (a)  CH 3  CHO  
Trace of an acid..
+H2O
19. (d) Liebermann’s Nitroso reaction.
Anil or Schiff's base
 1400 Nitrogen Containing Compounds
20. (a) CH 3 CONH 2  Br2  4 KOH  
2H O :C  N : :C  N :
2
(c) SO 3 H group being more acidic than CO 2 H group
(Acetamide)
6.
CH 3 NH 2  2 KBr  2 K 2 CO 3
(Methyl amine)
can easily transfer a proton to the amino group.

21. (c) The class of Indigo dye is Indigoid or vat dye. Indigo 
7. (a) HNO 3  2 H 2 SO 4 2 HSO 4  NO 2  H 3 O
dyes are insoluble in water.
 are not taking part in conjugation 8. (c) Only primary aliphatic amines can be prepared by
22. (d) Lone pair of N Gabriel phthalimide reaction.
whereas in other parts lone pairs are taking part in
9. (c) Reaction can be used to prepare 1°, 2°, 3° amines and
conjugation
finally quarternary ammonium salts.
H
CH 2  N 10. (b) Nitroarene cannot be distilled under normal
2
atmospheric pressure. This is because either they
CH 3 H CH 3 decompose or they explode on strong heating.
11. (c) Only 1° amines undergo Hofmann bromamide
23. (a) NO 2 reaction. Since CH 3 CONHCH 3 is a 2° amine
CH 3 O
therefore, it does not undergo Hofmann bromamide
reaction.
H Cl CH 3 12. (b) Nitrobenzene does not undergo Friedel Craft reaction
because nitro group deactivate the ring towards
CH 3 H CH 3 electrophilic substitution and drastic conditions are
needed to carry out the electrophilic substitution
reactions.
  CH 3 O
H 2O
NO 2
 Cl   13. (e) Ammonia is more basic than water. It is because
nitrogen being less electronegative than oxygen has a
–H+
H2O

H CH 3 greater tendency to donate electrons.

14. (c) Condensation of diazonium salt with phenol is
carried out in weakly alkaline medium, (pH  9) .
(Rearrangement

This is due to the fact that in strongly acid medium

the OH of a phenol remains unionised, and an
)

amine forms a salt. Phenol exists as phenoxide ion

and the latter is readily substituted by electrophiles
CH 3 H CH 3
than phenol itself. Thus, in phenol, coupling is
carried out in alkaline medium.
L  
H 2O
CH 3 O NO 2 15. (a) RNH 2  CHCl 3  3 KOH (alc)  R N 
 C  3 KCl
H 
 3 H 2O
H CH 3 17. (d) p-Anisidine is a stronger base than aniline.
OCH 3 group in anisidine exerts +R– effect.
Assertion and Reason 18. (b) Solubility of aldehydes and ketones decrease as the
molecular mass increase.
1. (a) It is true that benzene diazonium chloride does not 20. (d) The nitro group strongly deactivates the benzene
respond Lassaigne test of nitrogen because benzene ring towards electrophilic substitution.
diazonium chloride losses N 2 on Slight heat and thus Nitrobenzene does not undergo Friedel-Craft
it can't react with sodium metal. acylation reaction.
2. (a) Amines are basic due to the presence of a lone pair of 21. (a) In an isocyanide, first an electrophile and then a
electrons on nitrogen atom. The lone pair can be nucleophile add at the carbon to form a species which
easily donated. usually undergoes further transformations.
3. (b) The reason being that the terminal carbon atom in   
isocyanide has electron-deficient carbon having a R N  C  E   R N  CE 
 RN  C(Nu )E
Nu

sexlet of electrons and hence undergoes addition  

reactions with ozone. R N  C  H 2 O  RN  CHOH  RNHCHO
alkylformamide
4. (d) When primary amines are heated with chloroform in
the presence of alcoholic KOH, isocyanides are
formed. This reaction is known as carbylamine
reaction. eg. ethyl amine gives ethyl isocyanide on
treatment with CHCl 3 and alcoholic KOH.

C 2 H 5  NH 2  CHCl 3  3 KOH (alc) 
Ethyl amine Chloroform

C2 H 5  N  C  3 KCl  3 H 2 O
5. (b) Nucleophilic species which have more than one site of
reaction are called ambident nucleophiles.