12 AMINES

01
AMINES
AMINES 1

Previous Year Questions

character. Reactions of amines are governed by
availability of the unshared pair of electrons on
1. Arrange the following compounds as directed: (any
nitrogen. Influence of the number of hydrogen atoms at
Two)
nitrogen atom on the type of reactions and nature of
(i) In decreasing order of basic strength in aqueous
products is responsible for identification and distinction
solution :
between primary, secondary and tertiary amines.
C2H5NH2, (C2H5)2 NH, (C2H5)3 N Reactivity of aromatic amines can be controlled by
(ii) In increasing order of solubility in water: acylation process.
(C2H5)2 NH, C2H5NH2, C6H5 NH2 (i) Why does aniline not give Friedel-Crafts reaction?
(iii) In decreasing order of their pKb values : (ii) Arrange the following in the increasing order of their
C6H5 NH2, C2H5NH2, NH3 pKb values :

[CBSE-56-1-1-(2022)] C6H5NH2, NH3, C2H5NH2, (CH3)3N

2. (a) Illustrate the following reactions giving suitable (iii) How can you distinguish between CH3CH2NH2 and
example in each case: (CH3CH2)2NH by Hinsberg test?

(i) Gabriel phthalimide synthesis. (iv) (a) Write the structures of A and B in the following

(ii) Carbylamine reaction. reactions:

(iii) Hoffmann bromamide degradation reaction. (I)

OR

(b) Write the structures of A, B and C in the following

reactions:
(II) CH3CH2 CONH2 ⎯⎯⎯⎯⎯
Br2 /alc.KOH
→ A ⎯⎯⎯⎯
CH3 COCl
→B
(i) CH3CH2 Cl ⎯⎯⎯ → A ⎯⎯⎯ → B ⎯⎯⎯ →C
KCN LiAlH4 HNO2 Pyridine
0o C

OR
( )
(ii) CH3COOH ⎯⎯⎯ → A ⎯⎯⎯⎯
( b ) H2 O → B ⎯⎯⎯⎯→ C
NH3 a LiAlH
4 C6 H5SO2 Cl

(b) How will you convert the following:
[CBSE-56-1-1-(2022)] (I) Benzoic acid to aniline
3. Read the following passage and answer the questions (II) Aniline to p-bromoaniline
that follow: [CBSE-56-2-1-(2022)]
Amines constitute an important class of organic 4. An Organic compound (A) with molecular formula
compounds derived by replacing one or more hydrogen C3H7NO on heating with Br2 and KOH forms a
atoms of ammonia molecule by alkyl/aryl groups. compound (B). Compound (B) on heating with CHCl3
Amines are usually formed from nitro compounds, and alcoholic KOH produces a foul smelling compound
halides, amides, etc. They exhibit hydrogen bonding (C) and on reacting with C6H5SO2Cl forms a compound
which influences their physical properties. Alkyl amines (D) which is soluble in alkali. Write the structures of
are found to be stronger bases than ammonia. In (A), (B), (C) and (D).
aromatic amines, electron releasing and withdrawing
[CBSE-56-3-1-(2022)]
groups, respectively increase and decrease their basic
 2 AMINES

5. Give reasons : 8. (a) Account for the following:

(i) Ammonolysis of alkyl halides is not a good method (i) pkb of aniline is more than that of methylamine.
to prepare pure primary amines. (ii) Aniline does not undergo Friedel-Crafts reaction.
(ii) Aniline does not give Friedel-Crafts reaction. (iii) Primary amines have higher boiling points than
(iii) Although -NH2 group is o/p directing in tertiary amines.
electrophilic substitution reactions, yet aniline on OR
nitration gives good yield of m-nitroaniline.
(b) (i) Arrange the following compounds in the
[CBSE-56-3-1-(2022)] increasing order of their basic strength in aqueous
6. (a) Write reasons for the following: solution :

(i) Ethylamine is soluble in water whereas aniline is CH3 NH2, (CH3)3 N, (CH3)2NH
insoluble. (ii) What is Hinsberg's reagent?
(ii) Amino group is o- and p-directing in aromatic (iii) What is the role of pyridine in the acylation reaction
electrophilic substitution reactions, but aniline on of amines?
nitration gives a substantial amount of m-nitroaniline.
[CBSE-56-5-1-(2022)]
(iii) Amines behave as nucleophiles.
9. A compound 'A' on reduction with iron scrap and
OR hydrochloric acid gives compound 'B' with molecular
(b) How will you carry out the following conversions: formula C6H7N. Compound 'B' on reaction with CHCl3

(i) Nitrobenzene to Aniline and alcoholic KOH produces an obnoxious smell of

carbylamine due to the formation of 'C'. Identify 'A', 'B'
(ii) Ethanamide to Methanamine
and 'C' and write the chemical reactions involved.
(iii) Ethanenitrile to Ethanamine
[CBSE-56-5-1-(2022)]
[CBSE-56-4-1-(2022)]
10. CH3CONH2 on reaction with NaOH and Br2 in alcoholic
7. (a) Write equations involved in the following reactions:
medium gives:
(i) Ethanamine reacts with acetyl chloride.
(a) CH3COONa (c) CH3NH2
(ii) Aniline reacts with bromine water at room
(c) CH3CH2Br (d) CH3CH2NH2
temperature.
[CBSE-56-1-1-(2023)]
(iii) Aniline reacts with chloroform and ethanolic
11. Which of the following is least basic?
potassium hydroxide.
(a) (CH3)2NH (b) NH3
OR

(b) (i) Write the IUPAC name for the following

(c) (d) (CH3)3N
organic compound :
[CBSE-56-1-1-(2023)]
(CH3CH2)2NCH3
12. Assertion (A): –NH2 group is o-and p-directing in
(ii) Write the equations for the following :
electrophilic substitution reactions.
(I) Gabriel phthalimide synthesis
Reason (R): Aniline cannot undergo Friedel-Crafts
(II) Hoffmann bromamide degradation
reaction.
[CBSE-56-4-1-(2022)]
AMINES 1

(a) Both Assertion (A) and Reason (R) are true and
Reason (R) is the correct explanation of the Assertion
(A). (d)
(b) Both Assertion (A) and Reason (R) are true, but
Reason (R) is not the correct explanation of the
Assertion (A).
[CBSE-56-2-1-(2023)]
(c) Assertion (A) is true, but Reason (R) is false.
16. (a) (I) Give reasons :
(d) Assertion (A) is false, but Reason (R) is true.
(i) Aniline on nitration gives good amount of m-
[CBSE-56-1-1-(2023)]
nitroaniline, though - NH2 group is o/p directing in
13. Assertion (A): Acetylation of aniline gives a electrophilic substitution reactions.
monosubstituted product.
(ii) (CH3)2 NH is more basic than (CH3)3N in an aqueous
Reason (R): Activating effect of –NHCOCH3 group is solution.
more than that of amino group.
(iii) Ammonolysis of alkyl halides is not a good method
(a) Both Assertion (A) and Reason (R) are true and to prepare pure primary amines.
Reason (R) is the correct explanation of the Assertion
(II) Write the reaction involved in the following:
(A).
(i) Carbyl amine test
(b) Both Assertion (A) and Reason (R) are true, but
(ii) Gabriel phthalimide synthesis
Reason (R) is not the correct explanation of the
Assertion (A). (b) (I) Write the structures of A, B and C in the
following reactions:
(c) Assertion (A) is true, but Reason (R) is false.
(i)
(d) Assertion (A) is false, but Reason (R) is true.

[CBSE-56-1-1-(2023)]

14. Explain briefly :

(ii)
(a) Carbylamine reaction

(b) Gabriel phthalimide synthesis

[CBSE-56-1-1-(2023)]

15. Among the following, which is the strongest base?

(II) Why aniline does not undergo Friedal-Crafts
(a) reaction?

(Ill) Arrange the following in increasing order of their

boiling point:
(b) C2H5OH, C2H5NH2, (C2H5)3N

[CBSE-56-2-1-(2023)]

17. Among the following, which is the strongest base?

(c) (a)
 2 AMINES

20. The reduction of ethanenitrile with sodium and alcohol

gives :

(b) (a) 1-aminopropane

(b) 1-aminoethane

(c) Ethanoic acid

(d) Ethanamide
(c)
[CBSE-56-4-1-(2023)]

21. Assertion (A): Monobromination of aniline can be

conveniently done by protecting the amino group by
(d)
acetylation.

Reason (R): Acetylation decreases the activating effect

of the amino group.

[CBSE-56-3-1-(2023)] (a) Both Assertion (A) and Reason (R) are true and

18. Write the chemical equation involved in the following Reason (R) is the correct explanation of the Assertion

reactions : (A).

(a) Carbylamine reaction (b) Both Assertion (A) and Reason (R) are true, but
Reason (R) is not the correct explanation of the
(b) Gabriel phthalimide synthesis
Assertion (A).
[CBSE-56-3-1-(2023)]
(c) Assertion (A) is true, but Reason (R) is false.
19. Write the structures of A, B and C in the following
(d) Assertion (A) is false, but Reason (R) is true.
reactions:
[CBSE-56-4-1-(2023)]
(i)
22. Amines are usually formed from nitro compounds,
halides, amides, imides, etc. They exhibit hydrogen
bonding which influences their physical properties. In
alkyl amines, a combination of electron releasing, steric
(ii)
and hydrogen bonding factors influence the stability of
the substituted ammonium cations in protic polar
solvents and thus affect the basic nature of amines. In
aromatic amines, electron releasing and withdrawing
groups, respectively increase and decrease their basic
OR
character. Influence of the number of hydrogen atoms at
(b) How will you convert the following:
nitrogen atom on the type of reactions and nature of
(i) Aniline to p-bromoaniline products is responsible for identification and distinction
(ii) Ethanoic acid to methanamine between primary, secondary and tertiary amines.
(iii) Butanenitrile to 1-aminobutane Presence of amino group in aromatic ring enhances
reactivity of the aromatic amines. Aryl diazonium salts
[CBSE-56-3-1-(2023)]
provide advantageous methods for producing aryl
AMINES 1

halides, cyanides, phenols and arenes by reductive [CBSE-56-4-1-(2023)]

removal of the diazo group. 23. Which of the following would not be a good choice for
Answer the following questions : reducing nitrobenzene to aniline?

(i) Arrange the following in the increasing order of (a) LiAlH4 (b) H2/Ni
their pKb values in aqueous solution : (c) Fe and HCl (d) Sn and HCl
C2H5NH2, (C2H5)2NH, (C2H5)3N [CBSE-56-5-1-(2023)]
(ii) Aniline on nitration gives a substantial amount of m- 24. (a) (i) Draw the zwitter ion structure for sulphanilic
nitroaniline, though amino group is o/p directing. Why acid.
?
(ii) How canthe activating effect of –NH2
(iii) An aromatic compound 'A' of molecular formula group in aniline be controlled ?
C7H6O2 on treatment with aqueous ammonia and
OR
heating forms compound 'B'. Compound 'B' on heating
(b) (i) Complete the reaction with the main product
with Br2 and aqueous KOH gives a compound 'C' of
formed:
molecular formula C6H7N. Write the structures of A,
Band C.

OR

(iii) Complete the following reactions giving main

products : (ii) Convert Bromoethane to Propanamine.
(1) [CBSE-56-5-1-(2023)]

25. (a) Illustrate Sandmeyer's reaction with an equation.

(b) Explain, why (CH3)2NH is more basic than (CH3)3N

aqueous solution.

[CBSE-56-5-1-(2023)]
(2)
 2 AMINES

Solutions
(As no medium (aqueous /gaseous) or phase is given
both answers to be considered).
1. (i) (C2H5)2NH > (C2H5)3N > C2H5NH2
(iii) Add Hinsberg reagent (benzene sulphonyl chloride)
(ii) C6H5NH2 < (C2H5)2NH < C2H5NH2
to both the compounds. CH3CH2NH2 gives ppt. that is
(iii) C6H5NH2 > NH3 > C2H5NH2
soluble in alkali while the ppt. formed by (CH3CH2)2
2. (a) NH is insoluble in alkali.
(i) (iv) (a)

(I) (A) (B)

(II) (A) CH3CH2NH2 (B) CH3CH2NHCOCH3

OR

(b) (I)


(ii) R – NH2 + CHCl3 + 3KOH ⎯⎯ → RNC + 3KCl +
alc.

2H2O
(II)
(iii) R – CONH2 + Br2 + 4KOH → R – NH2 + K2CO3 +
alc./aq.

2KBr + 2H2O

OR

(b) (i) A = CH3CH2CN, B = CH3CH2CH2NH2, C =

CH3CH2CH2OH
4. (A) CH3CH2CONH2
(ii) A = CH3CONH2, B = CH3CH2NH2, C =
(B) CH3CH2NH2

(C) CH3CH2NC

(D)

3. (i) Aniline is a Lewis base and it reacts with AlCl3 to

form a salt / N of aniline acquires positive charge with
AlCl3 and hence is a deactivating group. 5. (i) Because it gives a mixture of amines which is
(ii) (CH3)3N < C2H5NH2 < NH3 < C6H5NH2 / difficult to separate.
C2H5 NH2 < (CH3)3N < NH3 < C6H5NH2
AMINES 1

(ii) Aniline is a Lewis base and it reacts with AlCl3 to

form a salt / N of aniline acquires positive charge with
AlCl3 and hence is a deactivating group.

(iii) Because of protonation of aniline / formation of

anilinium ion which deactivates the ring.

6. (a) (i) Ethylamine forms strong hydrogen bonds with

water molecules whereas in aniline due to the large
(II)
hydrocarbon part, the extent of H-bonding decreases.

(ii) Because of protonation of aniline / formation of

anilinium ion which deactivates the ring.

(iii) Amines behaves as nucleophiles due to the presence

8. (a) (i) lone pair of electrons are delocalised over benzene
of a lone pair of electrons on the nitrogen atom.
ring due to resonance, electron density decreases and
OR
hence less available for protonation / Due to electron
(b) (i)
withdrawing nature of the aryl group in aniline while
electron donating nature of methyl group in methyl
amine /Aniline is a weaker base than methylamine.

(ii) Aniline is a Lewis base and it reacts with AlCl3 to

form a salt / N of aniline acquires positive charge with
(ii) CH3CONH2 ⎯⎯⎯⎯
Br2 / KOH
→ CH3NH2
AlCl3 and hence is a deactivating group.
(iii) CH3CN ⎯⎯⎯
LiAlH4
→ CH3CH2NH2
(iii) Presence of intermolecular hydrogen bonding in
7. (a) (i) C2H5NH2 + CH3COCl ⎯⎯⎯
→ C2H5NHCOCH3
Base
primary amines which is absent in tertiary amines.
+ HCl OR
(ii) (b) (i) (CH3)3 N < CH3NH2 < (CH3)2NH

(ii) C6H5SO2Cl / Benzenesulphonyl chloride

(iii) Pyridine is used to remove HCl from the reaction

mixture.

9.
(iii)

OR

(b) (i) N-Ethyl-N-methylethanamine

(ii) (I)

10. (b)
 2 AMINES

11. (c)

12. (b)

13. (c)

14. (a) Aliphatic and aromatic primary amines on heating

with chloroform and ethanolic potassium hydroxide
form isocyanides or carbylamines which are foul-
smelling substances. / OR

R–NH2 + CHCl3 + 3KOH ⎯⎯⎯ (b) (I)

Heat
→ R–NC + 3KCl +
3H2O (i)

Isocyanide with an offensive smell is formed.

(Explanation or reaction)

(b) Phthalimide on treatment with ethanolic potassium

hydroxide forms potassium salt of phthalimide which on (ii)

heating with alkyl halide followed by alkaline

hydrolysis produces the corresponding primary amine/

(II) Because of the formation of salt with Lewis acid

anhydrous AlCl3.

(III) (C2H5)3N < C2H5NH2 < C2H5OH

17. (d)
15. (c)
18. (a) R – NH2 + CHCl3 + 3 KOH (alc.) → R – NC + 3KCl
16. (a) (I)
+ 3H2O
(i) Aniline gets protonated and is deactivated/ Aniline
(b)
on protonation forms anilinium ion which is meta-
directing.

(ii) Combination of inductive effect and solvation

effect.

(iii) Because it forms a mixture of amines that is difficult

to separate.

(II)
19.
(i) R – NH2 + CHCl3 + NaOH → RNC + 3NaCl + H2O
(a) (i)
(ii)
AMINES 1

(ii) A = CH3CH2CN, B = CH3CH2CH2NH2, C = (ii) Protecting /deactivating -NH2 group by acetylation

CH3CH2CH2OH or acylation.

20. (b) OR

21. (a) (b) (i)

22. (i) (C2H5)2NH < (C2H5)3N < C2H5NH2

(ii) Due to the protonation of aniline to form anilinium

ion which makes it deactivating and meta-directing.
(ii) CH3CH2Br ⎯⎯⎯
KCN
→ CH3CH2CN

⎯⎯⎯⎯⎯⎯⎯⎯→ H2 /Ni
or LiAlH4 or Na(Hg)/C2 H5 OH
CH3CH2CH2NH2
(iii) A =
25. (a)

B=

C= (b) Combination of inductive effect and solvation effect/

OR Due to greater H-bonding with water molecules,

(CH3)2NH shows more hydration or solvation effect.
(1)

(2)

23. (a)

24. (a) (i)