UNIT 09

AMINES

1 MARK QUESTIONS:

1) Arrange the following compounds in an increasing order of boiling point:

(C2H5)2NH, (C2H5)3N, C2H5NH2 AI 2020
2) Arrange the following compounds in an increasing order of their solubility in
water.
C6H5NH2, (C2H5)2NH, C2H5NH2 AI 2020, 2014 2011C, 2008; Delhi 2011
3) Arrange the following compounds in an increasing order of their basic strength
in aqueous solution: CH3NH2, (CH3)3N, (CH3)2NH AI 2020; Delhi 2013
4) Write the reaction involved in the Hofmann bromamide degradation reaction.
AI 2019
5) Propanamine and N,N-dimethylmethanamine contain the same amount of
carbon atoms, even though propanamine has higher boiling point than N,N-
dimethylmethanamine. Why? AI 2019
6) Arrange the following compounds in an increasing order of basic strength in gas
phase:
(C2H5)3N, C2H5NH2, (C2H5)2NH Delhi 2019
7) Write the IUPAC name of the following compound: (CH3)2N─CH2CH3 Delhi 2017
8) Write the IUPAC name of the following compound: (CH3CH2)2NCH3 Delhi 2017
9) Write the IUPAC name of the following compound: CH3NHCH(CH3)2 Delhi 2017
10) Arrange the following compounds in an increasing order of basic strength:
Aniline, p-nitroaniline, p-toluidine AI 2015C; Foreign 2008
11) Which of the two is more basic and why?

or Foreign 2014
12) Which of the two is more basic and why? CH3NH2 or NH3. Foreign 2014
13) Which of the two is more basic and why?

CH3NH2 or Foreign 2014

14) Out of CH3─NH2 and (CH3)3 N, which one has higher boiling point?
Delhi 2014C
15) Write the IUPAC name of the following compound:

AI 2014
 16) Arrange the following compounds in an increasing order of basic strength
C6H5NH2, C6H5NHCH3, C6H5CH2NH2 AI 2014
17) Arrange the following compounds in an increasing order of basic strength
C6H5NH2, C6H5NHCH3, C6H5N(CH3)2 AI 2014
18) Why does NH3 act as a Lewis base? Delhi 2014
19) Draw the structure of prop-2-en-1-amine. AI 2013
20) Draw the structure of N-methylethanamine. AI 2013
21) Draw the structure of 2-aminotoluene. AI 2013
22) Arrange the following compounds in an decreasing order of basic strength in
their aqueous solutions: NH3, CH3NH2, (CH3)2NH, (CH3)3N Delhi 2012
23) Rearrange the following compounds in an increasing order of their basic
strength:
C6H5NH2, C6H5N (CH3)2, (C2H5)2NH and CH3NH2 AI 2011
24) Give IUPAC name of H2N─CH2─CH2─CH=CH2. Delhi 2010
25) Write the isomer of C3H9N which gives foul smell of isocyanide when treated
with chloroform and ethanolic NaOH. AI 2020
26) Write the IUPAC name of the following:

Delhi 2013C
27) Complete the following reaction: C6H5N2Cl + H3PO2 + H2O → Delhi 2015C
28) How is the following conversion carried out:
Aniline to p-hydroxyazobenzene Delhi 2012C
29) Write one reaction that can be used as a test for primary amines.
Foreign 2011
30) Give a chemical test to distinguish between ethylamine and aniline.
AI 2011, 2010, 2009C
31) Give a chemical test to distinguish between aniline and N-methylaniline.
AI 2020
32) Why electrophilic substitution takes place more readily in aromatic amines
than benzene? Delhi 2010C

2 MARK QUESTIONS:

1) (i) Arrange the following compounds in an increasing order of basic strength:

C6H5NH2, C6H5N (CH3)2, (C2H5)2NH and CH3NH2
(ii) Arrange the following compounds in a decreasing order of pKb values:
C2H5NH2, C6H5NHCH3, (C2H5)2NH and C6H5NH2 AI 2014C
2) Give reasons:
(i) Aniline is a weaker base than cyclohexyl amine.
(ii) It is difficult to prepare primary amines by ammonolysis of alkyl halides.
All India 2013C
3) Write equations for
(i) Gabriel phthalimide reaction
(ii) Hofmann bromamide reaction Foreign 2011
4) Give a chemical test to distinguish between each of the following pairs of
compounds:
(i) Ethylamine and aniline.
(ii) Aniline and benzylamine. AI 2014C
5) Give a chemical test to distinguish between each of the following pairs of
compounds:
(i) Aniline and ethylamine
(ii) Ethylamine and dimethylamine Delhi 2013C
6) Complete the following reaction equations:
(i) C6H5N2Cl + H3PO2 + H2O →
(ii) C6H5NH2 + Br2 (aq) → All India 2012
7) Illustrate the following with an example of reaction in each case:
(i) Sandmeyer’s reaction
(ii) Coupling reaction. Delhi 2011C
8) Convert
(i) Nitrobenzene to phenol.
(ii) aniline to chlorobenzene Delhi 2015C
9) How will you convert
(i) aniline to benzonitrile?
(ii) ethanamine to ethanoic acid? Delhi 2011C
10) How will you bring about the following conversions?
(i) Methylamine into iodomethane
(ii) Chlorobenzene into p-chloroaniline Delhi 2011C
11) Give a chemical test to distinguish between
(i) Methylamine and dimethylamine
(ii) Aniline and n-methylaniline Delhi 2010
12) Explain the following reactions
(i) Gabriel phthalimide reaction
(ii) Coupling reaction Delhi 2013C
13) Describe the following giving the relevant chemical equation in each case:
(i) Carbylamine reaction.
(ii) Hofmann bromamide reaction All India 2012; Delhi 2012
14) How will you convert
(i) nitrobenzene to aniline?
(ii) aniline to iodobenzene Delhi 2011
15) Account for the following:
(i) Diazonium salts of aromatic amines are more stable than those of aliphatic
amines.
 (ii) Amines are more basic than alcohols of comparable molecular masses.
All India 2011C
16) (i) Why aniline does not undergo Friedel-Crafts reaction?
(ii) Why can primary aromatic amines be not prepared by Gabriel phthalimide
synthesis? All India 2011C
17) Identify A and B in each of the following processes:

(i)

(ii) All India 2010

18) Write one chemical reaction each to illustrate the following:
(i) Acetylation
(ii) Gabriel phthalimide synthesis Delhi 2010C

3 MARK QUESTIONS:

1) Give reason:
(i) Ammonolysis of alkyl halides is not a good method to prepare pure primary
amines.
(ii) Aniline does not give Friedel-Crafts reaction.
(iii) Although ─NH2 group is o/p directing in electrophilic substitution reactions,
yet aniline on nitration gives good yield of m-nitroaniline. 2022 (Term II)
2) Give reason:
(i) Aniline does not give Friedel-Crafts reaction.
(ii) Aromatic primary amines cannot be prepared by Gabriel’s phthalimide
synthesis.
(iii) Aliphatic amines are stronger bases than ammonia. Delhi 2020
3) State reasons for the following:
(i) pKb value of aniline is more than that of methylamine.
(ii) Ethylamine is soluble in water, whereas aniline is not soluble in water.
(iii) Primary amines have higher boiling points than tertiary amines.
All India 2011; Foreign 2010
4) An organic compound (A) with molecular formula C3H7NO on heating with Br2
and KOH forms a compound (B). Compound (B) on heating with CHCl 3 and
alcoholic KOH produces a foul smelling compound (C) and on reacting with
C6H5SO2Cl forms a compound (D) which is soluble in alkali. Write the
structures of (A), (B), (C) and (D). 2022 (Term II)
5) (i) Give one chemical test of distinguish between the compounds of the following
pairs:
a) CH3NH2 and (CH3)2NH
b) Aniline and ethanamine
(ii) Why aniline does not undergo Friedel-Crafts reaction? All India CBSE 2019
6) An aromatic compound ‘A’ on treatment with aqueous ammonia and heating
forms compound ‘B’ which on heating with Br2 and KOH forms a compound ‘C’
of molecular formula C6H7N. Write the structure and IUPAC names of
compounds A, B and C. Delhi 2015C
7) Give the structures of A, B and C in the following reactions:

(i)

(ii) All India 2014

8) How will you convert the following?
(i) Nitrobenzene into aniline
(ii) Ethanoic acid into methanamine
(iii) Aniline into n-phenylethanamide. (Write the chemical equations involved.)
All India 2014
9) Complete the following reactions:
(i) CH3CH2NH2 + CHCl3 + alc. KOH →

(ii)

(iii) All India 2013

10) Write the main products of the following reactions:

(i)

(ii)

(iii) All India 2013

11) Give the structures of A, B and C in the following reactions:

(i)

(ii) Delhi 2013

12) Write chemical equations for the following conversions:
(i) Nitrobenzene to benzoic acid
(ii) Benzyl chloride to 2-phenylethanamine
(iii) Aniline to benzyl alcohol. Delhi 2012
13) Give one chemical test each to distinguish between the compounds in the
following pairs:
(i) Methylamine and dimethylamine
 (ii) Aniline and benzylamine
(iii) Ethylamine and aniline All India 2011, 2010
14) Complete the following reactions:
(i) C6H5N2Cl + C6H5NH2 →
(ii) C6H5N2Cl + CH3CH2OH →
(iii) RNH2 + CHCl3 + KOH → Delhi 2010; Foreign 2010
15) An organic compound (A) on heating with Br2 and KOH forms a compound (B)
of molecular formula C6H7N which on reacting with CHCl3 and alcoholic KOH
produces a foul smelling compound (C). Write the structures and IUPAC names
of (A), (B) and (C). Delhi 2019
16) Do as directed:
(i) Arrange the following compounds in the increasing order of their basic
strength in aqueous solution: CH3NH2, (CH3)3N, (CH3)2NH
(ii) Identify ‘A’ and ‘B’:

2018C
(iii) Write equation of carbylamine reaction.
17) Write the structure of compounds A, B and C in the following reactions:

(i)

(ii)
All India 2017
18) Give reasons for the following:
(i) Acetylation of aniline reduces its activation effect.
(ii) CH3NH2 is more basic than C6H5NH2.
(iii) Although ─NH2 is o/p directing group, yet aniline on nitration gives a
significant amount of m-nitroaniline. Delhi 2017; All India 2017
19) Write the structure of A, B and C in the following:

(i)
(ii) Delhi 2016
20) Give the reasons for the following:
(i) aniline does not undergo Friedel-Crafts reaction
(ii) (CH3)2NH is more basic than (CH3)3N in an aqueous solution
(iii) Primary amines have higher boiling point than tertiary amines.
All India 2016, 2014
21) Write major product(s) in the following reactions:
(i)

(ii) All India 2016

 (iii) Delhi 2016C
22) Write the products A and B in the following:

(i)

(ii)
(iii) All India 2016C
23) Describe the method for the identification of primary, secondary and tertiary
amines. Also write chemical equations of the reaction involved.
24) Give the structures of A, B and C in the following reactions:

(i)

(ii) Delhi 2014

25) Account for the following:
(i) Aniline does not undergo Friedel-Crafts reaction.
(ii) Ethylamine is soluble in water, whereas aniline is not.
(iii) pKb of methylamine is less than that of aniline. Delhi 2014C
26) Write major product(s) in the following reactions:
(i)

(ii)

(iii) All India 2013

27) Complete the following reaction equations:

(i)
(ii) C6H5N2Cl + H3PO2 + H2O →
(iii) C6H5NH2 + Br2(aq) → All India 2012
28) Complete the following reaction equations:

(i)
(ii) C6H5𝑁2+Cl− + H3PO2 + H2O →

(iii) Delhi 2011; AI 2010; Foreign 2010

29) (i) Write one chemical reaction for each
a) Carbylamine reaction
 b) Acetylation reaction
(ii) Write structure of N,N-ethylmethylethanamide Delhi 2010C

5 MARK QUESTIONS:

1) (i) Write the reactions involved in the following:

a) Hofmann bromamide degradation reaction
b) Diazotization
c) Gabriel phthalimide synthesis
(ii) Give reasons:
a) (CH3)2NH is more basic than (CH3)3N in an aqueous solution.
b) Aromatic diazonium salts are more stable than aliphatic diazonium salts.
All India 2016C
2) (i) Write the structures of the main products of the following reactions:

a)

b)

c)
(ii) Give a simple chemical test to distinguish between aniline and
N, N- Dimethylaniline.
(iii) Arrange the following in the increasing order of their pKb values :
C6H5NH2, C2H5NH2, C6H5NHCH3
3) An aromatic compound ‘A’ of molecular formula C7H6O2 undergoes a series of
reactions as shown below. Write the structures of A, B, C, D and E in the
following reactions.

All India 2015

4) (i) Write the structures of main products when benzene diazonium chloride
reacts with the following reagents:
 a) H3PO2 + H2O b) CuCN/KCN c) H2O
(ii) Arrange the following in the increasing order of their basic character in an
aqueous solution: C2H5NH2, (C2H5)2NH, (C2H5)3N
(iii) Give a simple chemical test to distinguish between the following pair of
compounds: C6H5─NH2 and C6H5─NH─CH3 All India 2015
5) An aromatic compound ‘A’ of molecular formula C7H7ON undergoes a series of
reactions as shown below. Write the structures of A, B, C, D and E in the
following reactions:

Delhi 2015
6) (i) Write the structures of main products when aniline reacts with the following
reagents: a) Br2 water b) HCl c) (CH3CO)2O/pyridine
(ii) Arrange the following in the increasing order of their boiling point:
C2H5NH2, C2H5OH, (CH3)3N
(iii) Give a simple chemical test to distinguish between the following pair of
compounds: (CH3)2NH, (CH3)3N Delhi 2015
7) (i) Illustrate the following reactions giving suitable example in each case:
a) Ammonolysis
b) Coupling reaction
c) Acetylation of amines
(ii) Describe Hinsberg method for the identification of primary, secondary and
tertiary amines. Also, write the chemical equations of the reactions
involved. Foreign 2015
8) (i) Write the structures of main products when benzene diazonium chloride
(C6H5N2+Cl-) reacts with the following reagents:
a) HBF4/∆ b) Cu/HBr
(ii) Write the structures of A, B and C in the following reactions:

a)

b) Foreign 2015