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13.3 Nomenclature 10. Write the structures of A and B in the

following reaction :
VSA (1 mark) CH3COOH
NH3
A
NaOBr
B
D
1. Write IUPAC name of the following (1/5, 2020)
compound : (CH3CH2)2NCH3 11. Carry out the following conversion :
(Delhi 2017) Benzoic acid to aniline. (1/5, AI 2019)
2. Write the structure of 12. Write the chemical equation involved in the
2, 4-dinitrochlorobenzene. (Delhi 2017) following reaction :
Hofmann bromamide degradation reaction
3. Write the IUPAC name of the following
(AI 2019, 1/5, 2018, 1/2, AI 2016, 2012,
compound : 1/3, Foreign 2011)
CH3NHCH(CH3)2 (Delhi 2017)
13. State and illustrate the following :
4. Write IUPAC name of the following compound: Gabriel synthesis (1/5, 2018, 1/2, AI 2013C,
(CH3)2N — CH2CH3 (Delhi 2017) 1/3, Foreign 2011)
5. Write the IUPAC name of the given 14. How do you convert the following :
compound : Ethanenitrile to ethanamine (1/3, AI 2015)
NH2 15. Write chemical equation for the following
Br Br conversion :
Benzyl chloride to 2-phenylethanamine.
(1/3, Delhi 2012)
Br (Delhi 2016) 16. Why cannot primary aromatic amines be
prepared by Gabriel phthalimide synthesis?
6. Write the structure of N-methylethanamine. (1/2, AI 2011C)
(AI 2013)
7. Write the structure of 2-aminotoluene. SA (2 marks)
(AI 2013) 17. How will you convert the following :
(i) Nitrobenzene into aniline
SA (2 marks) (ii) Ethanoic acid into methanamine
8. Give IUPAC names of the following (2/3, Delhi 2014)
compounds : 18. How are the following conversions carried out?
(a) CH2 CH CH NH2 (i) CH3CH2Cl to CH3CH2CH2NH2
CH3 (ii) Benzene to aniline (Delhi 2012C)
O
13.5 Physical Properties
NH C CH3
VSA (1 mark)
(b) (Delhi 2012C) 19. Out of CH3NH2 and CH3OH, which has
higher boiling point?(2020)
13.4 Preparation of Amines 20. Arrange the following compounds in
VSA (1 mark) decreasing order of their boiling points :
Butanol, Butanamine, Butane (1/3, 2020)
9. Ammonolysis of alkyl halides is not a good
method to prepare pure primary amines. 21. Propanamine and N, N-dimethylmethanamine
(1/5, 2020) contain the same number of carbon atoms,
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even though propanamine has higher boiling

point than N, N-dimethylmethanamine. Why? (c) CH2CN
(AI 2019)
22. Give reasons for the following : (d) CH2Cl (2020)
Primary amines have higher boiling point
than tertiary amines. 30. Arrange the following compounds as
(1/3, AI 2016, 2014, 2011) directed :
23. Arrange the following in the increasing order In decreasing order of basic strength in
of their boiling points : aqueous solution :
C2H5NH2, C2H5OH, (CH3)3N (CH3)3N, (CH3)2NH, CH3NH2 (1/3, 2020)
(1/5, Delhi 2015) 31. Give the structures of A and B in the
24. Arrange the following compounds in following sequence of reactions :
increasing order of solubility in water : Fe/HCl2 NaNO +HCl
C6H5NH2, (C2H5)2NH, C2H5NH2 C 6 H5 NO2 
→ A →B
0°−5°C
(Delhi 2014, AI 2011C) (2/3, 2020)
25. Out of CH3NH2 and (CH3)3N, which one has 32. Arrange the following in increasing order of
higher boiling point? (Delhi 2014C) base strength in gas phase.
(C2H5)3N, C2H5NH2, (C2H5)2NH
26. Account for the following :
(Delhi 2019)
Ethylamine is soluble in water whereas aniline
is not. (1/3, Delhi 2014C, AI 2011) 33. Carry out the following conversion :
Bromomethane to ethanol. (1/5, AI 2019)
SA (2 marks) 34. Give reason :
27. Arrange the following compounds as (CH3)2NH is more basic than (CH3)3N in an
directed : aqueous solution. (1/5, 2018)
(i) In increasing order of solubility in water : 35. Arrange the following in the decreasing order
(CH3)2NH, CH3NH2, C6H5NH2 of their basic strength in aqueous solutions :
CH3NH2, (CH3)2NH, (CH3)3N and NH3
(ii) In increasing order of boiling point :
(1/3, 2018C, Delhi 2012)
(C2H5)2NH, (C2H5)3N, C2H5NH2
36. Describe the following by giving the relevant
(2/3, 2020)
chemical equation :
Carbylamine reaction
13.6 Chemical Reactions (Amines) (1/3, 2018C, 1/2, AI 2012)
VSA (1 mark) 37. Give a simple chemical test to distinguish
between the following pair of compounds :
28. Out of the following, the strongest base in (CH3)2NH and (CH3)3N (1/5, Delhi 2015)
aqueous solution is 38. Arrange the following in increasing order of
(a) methylamine (b) dimethylamine basic strength :
(c) trimethylamine (d) aniline.(2020) Aniline, p-nitroaniline and p-toluidine
(1/2, AI 2015, AI 2015C)
29. CH2 NH2 on heating with
39. Arrange the following in increasing order of
CHCl3 and alcoholic KOH gives foul smell of basic strength :
C6H5NH2, C6H5NHCH3, C6H5CH2NH2
(a) (1/2, AI 2015, Delhi 2014)
CH2OH
40. How will you convert the following :
Aniline into N-phenylethanamide
(b) CH2NC (Write the chemical equations involved.)
(1/3, Delhi 2014)
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41. Arrange the following in increasing order of yet aniline, on nitration gives good yield
basic strength : of m-nitroaniline.
C6H5NH2, C6H5NHCH3, C6H5N(CH3)2 (ii) (CH3)2NH is more basic than (CH3)3N
(Delhi 2014) in an aqueous solution. (2/5, 2020)
42. Which of the two is more basic and why? 55. Write the structures of the main products of
CH3NH2 or NH3 (Foreign 2014) the following reactions :
43. Which of the two is more basic and why? NH2
NH2 NH2
(CH3CO)2O
(i)
and Pyridine

(CH3)2NH
CH3 (ii) SO2Cl
(Foreign 2014)
44. Which of the two is more basic and why? (2/5, 2018)
NH2 56. (a) Give a simple chemical test to
distinguish between aniline and
CH3NH2 or (Foreign 2014) N, N-dimethylaniline.
(b) Arrange the following in the increasing
45. Arrange the following in increasing order of
order of their pKb values :
their basic strength in aqueous solution :
C6H5NH2, C2H5NH2, C6H5NHCH3
CH3NH2, (CH3)3N, (CH3)2NH (Delhi 2013)
(2/5, 2018)
46. Complete the following reaction equation :
57. Give reasons for the following :
C6H5NH2 + Br2(aq) → (1/2, AI 2012)
(i) Aniline does not undergo Friedel–
47. Rearrange the following in an increasing Crafts reaction.
order of their basic strengths : (ii) (CH3)2NH is more basic than (CH3)3N
C6H5NH2, C6H5N(CH3)2, (C6H5)2NH and in an aqueous solution.
CH3NH2 (AI 2011) (2/3, AI 2016, 2014)
48. State reasons for the following : 58. How do you convert the following :
pKb value for aniline is more than that for (i) C6H5CONH2 to C6H5NH2
ethylamine. (1/3, AI 2011) (ii) Aniline to phenol
49. How will you differentiate between aniline (2/3, AI 2015)
and ethylamine? (AI 2011) 59. Illustrate the following reactions giving
50. Why is an alkylamine more basic than suitable example in each case :
ammonia? (Foreign 2011) (i) Ammonolysis
51. How will you bring about the following (ii) Acetylation of amines
conversion : (2/5, Foreign 2015)
Ethanamine to ethanoic acid (Delhi 2011C) 60. Give the structures of A, B and C in the
following reactions :
SA (2 marks)
(i) C6H5NO2 A B
52. How will you distinguish between the
following pairs of compounds : C
(i) Aniline and ethanamine (ii) CH3CN A B
(ii) Aniline and N-methylaniline
(2/3, 2020) C
53. Distinguish between the following : (2/3, Delhi, AI 2014)
(i) CH3CH2NH2 and (CH3CH2)2NH 61. Account for the following :
(ii) Aniline and CH3NH2 (2/5, 2020) (i) Aniline does not give Friedel–Crafts
54. Give reasons : reaction.
(i) Although NH2 group is o/p directing (ii) pKb of methylamine is less than that of
in electrophilic substitution reactions, aniline. (2/3, Delhi 2014C)
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62. (i) Arrange the following compounds in an LA I (3 marks)

increasing order of basic strength :
C6H5NH2, C6H5N(CH3)2, (C2H5)2NH 69. (a) Write the chemical reaction of methyl
and CH3NH2 amine with benzoyl chloride and
write the IUPAC name of the product
(ii) Arrange the following compounds in a
obtained.
decreasing order of pKb values :
(b) Arrange
 the following in the increasing
C2H5NH2, C6H5NHCH3, (C2H5)2NH
order of their pKb values :
and C6H5NH2
C6H5NH2, NH3, C2H5NH2, (C2H5)2NH
(Delhi 2014C)
(3/5, 2020)
63. Complete the following reactions :
70. (a) Give one chemical test to distinguish
(i) CH3CH2NH2 + CHCl3 + alc. KOH between the compounds of the
NH2 following pairs :
(i) CH3NH2 and (CH3)2NH
(ii) + HCl(aq) (2/3, AI 2013) (ii) Aniline and ethanamine
(b) Why aniline does not undergo Friedel–
64. Write the main products of the following Crafts reaction? (AI 2019)
reactions : 71. Give reasons :
NH2 (i) Acetylation of aniline reduces its
activation effect.
Br2(aq)
(i) ? (ii) CH3NH2 is more basic than C6H5NH2.
(iii) Although —NH2 is o/p directing
Br2 + NaOH group, yet aniline on nitration gives a
(ii) CH3 C NH2 ? significant amount of m-nitroaniline.
(2/3, AI 2013) (Delhi 2017)
O
65. Give chemical tests to distinguish between 72. Write the structures of A, B and C in the
the following pairs of compounds : following :
Br2/aq. KOH
(i) Aniline and ethylamine (i) C6H5 CONH2 A
(ii) Ethylamine and dimethylamine KI NaNO2 +HCl
(Delhi 2013C) C B
0-5°C
66. Give reasons : KCN LiAlH4
(ii) CH3 Cl A B
(i) Aniline is a weaker base than cyclohexyl
CHCl3 + alc. KOH
amine. C

(ii) It is difficult to prepare pure amines by (Delhi 2016)
ammonolysis of alkyl halides.
73. Write the structures of main products when
(AI 2013C)
aniline reacts with the following reagents :
67. Give reasons :
(i) Br2 water (ii) HCl
(i) Electrophilic substitution in aromatic
(iii) (CH3CO)2O/pyridine (3/5, Delhi 2015)
amines takes place more readily than
benzene. 74. Write the chemical equations involved when
(ii) CH3CONH2 is weaker base than aniline is treated with the following reagents :
CH3CH2NH2. (AI 2013C) (i) Br2 water (ii) CHCl3 + KOH
(iii) HCl (AI 2015)
68. How would you account for the following :
75. Write the structures of A, B and C in the
(i) Aniline is a weaker base than
cyclohexylamine. following reactions :
Sn + HCl NaNO2 + HCl
(ii) Methylamine in aqueous medium gives (i) C6H5NO2 A 273 K B
reddish-brown precipitate with FeCl3. H2O
(AI 2012C) C ∆
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KCN LiAlH4 HNO2 85. How is the following conversion carried out :
(ii) CH3Cl A B 273 K C
Aniline to p-hydroxyazobenzene.
(3/5, Foreign 2015)
(1/2, Delhi 2012C)
76. An aromatic compound ‘A’ on treatment with
aqueous ammonia and heating forms compound 86. How will you bring about the following
‘B’ which on heating with Br2 and KOH forms conversion :
a compound ‘C’ of molecular formula C6H7N. Nitrobenzene to phenol (1/2, Delhi 2011C)
Write the structures and IUPAC names of
87. How will you bring about the following
compounds A, B and C. (Delhi 2015C)
conversion : Aniline to chlorobenzene
77. Give the structures of products A, B and C in
Write the chemical equation involved.
the following reactions :
LiAlH4 HNO2
(1/2, Delhi 2011C)
KCN
(i) CH3CH2Br A B 0°C C 88. How will you bring about the following
NH3 NaOH + Br2 conversion :
(ii) CH3COOH ∆ A B
CHCl3 + Aniline to benzonitrile. (Delhi 2011C)
Alc. NaOH
C SA (2 marks)
(Delhi 2014, 2013) 89. (a) Write the reaction involved in the following :
13.9 Chemical Reactions Diazotisation
(Diazonium salts) (b) Give reason :
Aromatic
 diazonium salts are more
VSA (1 mark)
stable than aliphatic diazonium salts.
78. Write the structures of A and B in the (2/5, 2018)
following reactions :
CuCN H2O/H+ 90. Write chemical equations for the following
C6H6N+2Cl– A B conversions :
(1/5, 2020) (i) Nitrobenzene to benzoic acid.
79. Carry out the following conversion : (ii) Aniline to benzyl alcohol.
p-nitrotoluene to 2-bromobenzoic acid. (2/3, Delhi 2012)
(1/5, AI 2019)
91. Illustrate the following with an example of
80. Write the structure of the main product of
reaction in each case :
the following reaction :
+ (i) Sandmeyer reaction
N2Cl– CH CH OH (ii) Coupling reaction.
3 2
(1/5, 2018)
(AI 2012C, Delhi 2011C)
81. Complete the following reaction equation : LA I (3 marks)
C6H5N2Cl + H3PO2 + H2O
(Delhi 2015C, AI 2013, 2012) 92. Write the structures of main products when
benzene diazonium chloride reacts with the
82. The conversion of primary aromatic
following reagents :
amines into diazonium salts is known as
(i) CuCN (ii) CH3CH2OH
__________. (AI 2014)
(iii) KI (Delhi 2019)
83. Complete the following reaction :
H2O 93. Write the structures of compounds A, B and
C6H5N2+Cl– (Room temp.)
(1/3, AI 2013) C in the following reactions :
84. State and illustrate the following : NH /D Br2/KOH(aq)
(a) CH3—COOH →
3
A →
Coupling reaction CHCl + alc. KOH
(1/2, AI 2013C, Foreign 2011) B →
3
C
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NaNO /Cu Fe/HCl (C7H7ON) A

(b) C6H5N+2BF–4 →
2
A →
D
CH3COCl/pyridine CH3CH2OH NaNO2 + HCl
B → C C B C6H5NH2
273 K
(AI 2017) CHCl3
KI +
NaOH
94. Give the structure of A, B and C in the
following reactions : E D
(Delhi 2015)
H2O/H + NH3
(i) C6H5N2+Cl– CuCN A B 
C 96. (i) Write the structures of main products
when benzenediazonium chloride
(ii) (C6H5N2+Cl–) reacts with the following
reagents :
(a) HBF4/D (b) Cu/HBr
(ii) Write
 the structures of A, B and C in the
(Delhi 2013) following reactions :
LA II (5 marks) (a)
95. An aromatic compound ‘A’ of molecular
formula C7H7ON undergoes a series of
reactions as shown below. Write the structures KCN LiAlH4 HNO2
(b) CH3Cl A B 273 K C
of A, B, C, D and E in the following reactions :
(Foreign 2015)