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◎ Chapter 9
F Amines

¥ 6 Marks
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Syllabus
Amines : Nomenclature, classification,
structure, methods of preparation,
physical and chemical properties, uses,
identification of primary, secondary and
tertiary amines.
Diazonium salts : Preparation, chemical
reactions and importance in synthetic
organic chemistry.
§ 2024 SQP
™ Question 1
In which of the following solvents, the
+ –
C4H8NH3 X is soluble
(a) ether (b) acetone
(c) water (d) bromine water
A Answer ¥ 1 Marks
(c) water

™ Question 2
An organic compound with molecular formula
C7H7NO2 exists in three isomeric forms, the
isomer ‘A’ has the highest melting point of the
three. ‘A’ on reduction gives compound ‘B’ with
molecular formula C7H9N. ‘B’ on treatment with
NaNO2/HCl at 0-5°C to form compound ‘C’. On
treating C with H3PO2 ,it gets converted to D with
formula C7H8 , which on further reaction with
CrO2Cl2 followed by hydrolysis forms ‘E’ C7H6O.
Write the structure of compounds A to E. Write
the chemical equations involved.
A Answer ¥ 5 Marks
Compound A is p-methylnitrobenzene
Compound B is p-methylbenzenamine
Compound C is p-methylbenzenediazoiumchloride
Compound D - Toluene
Compound E - Benzaldehyde

The chemical reactions involved are

O
CH3 CH3 CH3 CH3 C H

Sn / HCl NaNO2/HCl H3PO2 CrO2Cl2

−−−−→ −−−−−−
◦ ◦
→ −−−→ −−−−→
+
0 C–5 C H3O

NO2 NH2 N2Cl

 ™ OR
(a) Account for the following:
(i) N-ethylbenzenesulphonyl amide is soluble in
alkali .
(ii) Reduction of nitrobenzene using Fe and HCl is
preferred over Sn and HCl.
(b) Arrange the following in:
(i) decreasing order of pKb values
C6H5NH2, C6H5NHCH3, C6H5CH2NH2,
CH3NH2, NH3
(ii) increasing order of solubility in water
C2H5Cl, C2H5NH2, C2H5OH
(iii) decreasing boiling point
CH3COOH, C2H5OH, CH3NH2, CH3OCH3

A Answer ¥ 5 Marks
Section (a)
(i) The hydrogen attached to N-Ethylbenzene
sulphonamide is acidic in nature. This is due
to the presence of strong electron withdrawing
sulphonyl group. Hence, it is soluble in alkali.
(ii) Reduction with iron scrap and hydrochloric
acid is preferred because FeCl2 formed gets
hydrolysed to release hydrochloric acid during
the reaction. Thus, only a small amount of
hydrochloric acid is required to initiate the
reaction.
Section (b)
(i) C6H5NH2 > C6H5NHCH3 > NH3 >
C6H5CH2NH2 > CH3NH2
(ii) C2H5Cl < C2H5NH2 < C2H5OH
(iii) CH3COOH > C2H5OH > CH3NH2 > CH3OCH3
§ 2023 56/C Compart
™ Question 3
Three compounds are given below :
NH2 NH2 NH2

NO2 CH3
I II III
The correct decreasing order of their basic
strength is :
(a) II > III > I (b) III > II > I
(c) III > I > II (d) I > III > II
A Answer ¥ Set 1, 1 Marks
(a) II > III > I

Theory Recap

If you write different resonating structures of

aniline, you will find that aniline is a resonance
hybrid of the following five structures. On the
other hand, anilinium ion obtained by accepting a
proton can have only two resonating structures
(kekule).
Thus, greater the number of resonating
structures, greater is the stability. Aniline (five
resonating structures) is more stable than
anilinium ion. Hence, the proton acceptability or
the basic nature of aniline or other aromatic
amines would be less than that of ammonia.
In case of substituted aniline, it is observed that
electron releasing groups like – OCH3, – CH3
increase basic strength whereas electron
withdrawing groups like – NO2, – SO3H, – COOH,
-X decrease it.

™ Question 4
Three compounds are given below :
C2H5NH2 (I), (C2H5)2NH (II), (C2H5)3N (III)
The correct decreasing order of their basic
strength in an aqueous solution is :
(a) II > III > I (b) III > II > I
(c) I > II > III (d) I > III > II
A Answer ¥ Set 2, 1 Marks
(a) II > III > I

Theory Recap

Due to the electron releasing nature of alkyl

group, it (R) pushes electrons towards nitrogen
and thus makes the unshared electron pair more
available for sharing with the proton of the acid.
Moreover, the substituted ammonium ion formed
from the amine gets stabilised due to dispersal of
the positive charge by the +I effect of the alkyl
group. Hence, alkylamines are stronger bases
than ammonia.
Thus, the basic nature of aliphatic amines should
increase with increase in the number of alkyl
groups. This trend is followed in the gaseous
phase.
The order of basicity of amines in the gaseous
phase follows the expected order: tertiary amine
> secondary amine > primary amine > NH3. The
trend is not regular in the aqueous state as
evident by their pKb values

™ Question 5
Three compounds are given below :
(C2H5)3N (I), C2H5NH2 (II), (C2H5)2NH (III)
Identify the correct decreasing order of their basic
strength in gas phase :
(a) II > III > I (b) III > I > II
(c) III > II > I (d) I > III > II
A Answer ¥ Set 1, 1 Marks
(c) III > II > I

Theory Recap

In the aqueous phase, the substituted ammonium

cations get stabilised not only by electron
releasing effect of the alkyl group (+I) but also by
solvation with water molecules. The greater the
size of the ion, lesser will be the solvation and the
less stabilised is the ion.
Greater is the stability of the substituted
ammonium cation, stronger should be the
corresponding amine as a base. Thus, the order of
basicity of aliphatic amines should be: primary >
secondary > tertiary, which is opposite to the
inductive effect based order.
Secondly, when the alkyl group is small, like
– CH3 group, there is no steric hindrance to
H-bonding. In case the alkyl group is bigger than
CH3 group, there will be steric hinderance to
H-bonding. Therefore, the change of nature of
the alkyl group, e.g., from – CH3 to – C2H5 results
in change of the order of basic strength.
Thus, there is a subtle interplay of the inductive
effect, solvation effect and steric hinderance of
the alkyl group which decides the basic strength
of alkyl amines in the aqueous state.

™ Question 6
Hoffmann Bromamide Degradation reaction is
given by

NO2

(a) (b)
O
(c) CH3 – C –
–N (d) CH3 CH2 C NH2
A Answer ¥ Set 1, 1 Marks
O
(d) CH3 CH2 C NH2
 Theory Recap

Hoffmann developed a method for preparation of

primary amines by treating an amide ( – CONH2)
with bromine in an aqueous or ethanolic solution
of sodium hydroxide. In this degradation
reaction, migration of an alkyl or aryl group takes
place from carbonyl carbon of the amide to the
nitrogen atom. The amine so formed contains one
carbon less than that present in the amide.

™ Question 7
Assertion (A) : Benzene diazonium salt is stable
and can be easily stored.
Reason (R) : Benzene diazonium chloride
decomposes easily.
(a) Both Assertion (A) and Reason (R) are true
and Reason (R) is the correct explanation of
the Assertion (A).
(b) Both Assertion (A) and Reason (R) are true,
but Reason (R) is not the correct explanation
of the Assertion (A).
(c) Assertion (A) is true, but Reason (R) is false.
(d) Assertion (A) is false, but Reason (R) is true.
A Answer ¥ Set 1, 1 Marks
Assertion (A) is false, but Reason (R) is true.

Theory Recap

Benzenediazonium chloride is prepared by the

reaction of aniline with nitrous acid at 273-278K.
Nitrous acid is produced in the reaction mixture
by the reaction of sodium nitrite with
hydrochloric acid. The conversion of primary
aromatic amines into diazonium salts is known as
diazotisation. Due to its instability, the
diazonium salt is not generally stored and is
used immediately after its preparation.
Primary aliphatic amines form highly unstable
alkyldiazonium salts. Primary aromatic amines
form arenediazonium salts which are stable for a
short time in solution at low temperatures

™ Question 8
Answer any three of the following questions :
Give reasons for the following :
(a) Reduction with iron scrap and HCl is preferred
for the preparation of amines from nitro
 compounds.
(b) Lower aliphatic amines are soluble in water.
(c) Pyridine is used in the acylation reaction of
amines.
(d) Although amino group is o- and p-directing in
aromatic electrophilic substitution reactions,
aniline on nitration gives a substantial amount
of m-nitroaniline.
A Answer ¥ Set 1, 3 Marks
(a) FeCl2 formed gets hydrolysed to release HCl
during the reaction. Thus, a small amount of
HCl is needed to initiate the reaction.
(b) Lower aliphatic amines can form hydrogen
bonding with water.
(c) Pyridine removes HCl and shifts the
equilibrium in the forward direction.
(d) Due to the formation of anilinium ion which is
m-directing.

™ Question 9
Answer any three of the following questions :
Give reasons for the following :
(a) Acylation of -NH2 group is done in aniline
before preparing its ortho and para
compounds.
(b) Solubility of amines decreases with increase in
molar mass of amines.
(c) Aniline does not undergo Friedel-Crafts
reaction.
(d) Primary amines have higher boiling points
than tertiary amines.
A Answer ¥ Set 2, 3 Marks
(a) Due to resonance electron density on nitrogen
gets reduce and is less available for donation.
(b) The extent of hydrogen bonding with water is
reduced due to an increase in the size of the
alkyl group.
(c) Due to the salt formation with Lewis acid
anhydrous AlCl3.
(d) Due to the presence of intermolecular
hydrogen bonding in primary amines which is
absent in tertiary amines.

™ Question 10
Answer any three of the following questions :
 Give reasons for the following :
(a) Diazonium salts of aromatic amines are more
stable than aliphatic amines.
(b) Amines are less soluble in water as compared
to alcohols.
(c) How is the basic strength of aromatic amines
affected by the presence of an electron
releasing group ?
(d) Why does amino group in aniline act as a
powerful activator and ortho and para
directing towards electrophilic substitution ?
A Answer ¥ Set 3, 3 Marks
(a) Due to resonance in aromatic diazonium salt.
(b) Because N – H bond is less polar than O – H
bond which results in weak hydrogen bonding
with water in amines.
(c) Basic strength increases due to increase in
electron density on nitrogen ,which makes
easy availability of lone pair of electrons.
(d) Due to resonance electron density increases at
ortho and para positions.
§ 2023 56(B) Compart
š Question 11
Assertion (A) : Ammonolysis of alkyl halides is
not a suitable method for the preparation of pure
primary amines.
Reason (R) : Ammonolysis of alkyl halides
yields mainly tertiary amines.
(a) Both Assertion (A) and Reason (R) are true
and Reason (R) is the correct explanation of
the Assertion (A).
(b) Both Assertion (A) and Reason (R) are true,
but Reason (R) is not the correct explanation
of the Assertion (A).
(c) Assertion (A) is true, but Reason (R) is false.
(d) Assertion (A) is false and Reason (R) is also
false.
A Answer ¥ Set 1, 1 Marks
Assertion (A) is true, but Reason (R) is false.

Theory Recap
When the ammonolysis reaction is carried out (in
a sealed tube at 373 K), the primary amine thus
obtained behaves as a nucleophile and further
react with alkyl halide to form secondary and
tertiary amines, and finally quaternary
ammonium salt. Thus, ammonolysis has the
disadvantage of yielding a mixture of primary,
secondary and tertiary amines and also a
quaternary ammonium salt.
However, primary amine is obtained as a major
product by taking large excess of ammonia. The
order of reactivity of halides with amines is
RI > RBr > RCl.

Ammonolysis

The carbon-halogen bond in alkyl or benzyl

halides can be easily cleaved by a nucleophile.
Hence, an alkyl or benzyl halide on reaction with
an ethanolic solution of ammonia undergoes
nucleophilic substitution reaction in which the
halogen atom is replaced by an amino ( – NH2)
group. This process of cleavage of the C–X bond
by ammonia molecule is known as ammonolysis.
š Question 12
Write the reaction involved in :
(a) Hoffmann-bromamide reaction, and
(b) Carbylamine reaction
A Answer ¥ Set 1, 2 Marks
O
(a) R C NH2 + Br2 + 4 NaOH −−→ R – NH2 + NA2CO3 + 2 NABr + 2 H2O
Heat
(b) R – NH2 + CHCl3 + 3KOH −−−−→ R – NC + 3KCl + 3H2O
 š Question 13
What happens when aniline is treated with
(a) Br2 water?
(b) Conc. HNO3 ?
(c) CH3COCl/ Pyridine ?
A Answer ¥ Set 1, 3 Marks
NH2 NH2
Br Br
Br2/H2O
(a) + 3Br2 −−−−→

Br
2,4,6-Tribromoaniline is formed.
(b) p-Benzoquinone
NH2 NHCOCH3

(CH3CH)2O
(c) −−−−−−→
Pyridine

Acetanilide is formed
§ 2023 56(B) March
š Question 14
The Gabriel phthalimide synthesis is used for the
preparation of :
(a) primary aromatic amines
(b) primary aliphatic amines
(c) secondary amines
(d) tertiary amines
A Answer ¥ Set 1, 1 Marks
(b) primary aliphatic amines
š Question 15
The action of nitrous acid on ethylamine gives
mainly :
(a) ethyl nitrite
(b) ethane
(c) nitroethane
(d) ethyl alcohol
A Answer ¥ Set 1, 1 Marks
(d) ethyl alcohol
š Question 16
 Amines can be considered as derivatives of
ammonia obtained by replacement of hydrogen
atoms with alkyl or aryl groups. Like ammonia,
all the three types of amines have one unshared
electron pair on nitrogen atom due to which they
behave as Lewis bases. Amines are usually
formed from nitro compounds, halides, amides,
etc. They exhibit hydrogen bonding which
influences their physical properties. Alkyl amines
are found to be stronger bases than ammonia. In
aromatic amines, electron releasing and
withdrawing groups, respectively increase and
decrease their basic character.
Answer the following :
(i) Out of aniline and methylamine, which is a
stronger base and why ?
(ii) Why does tertiary amine have lower boiling
point than primary amine of comparable
molecular masses ?
(iii) What happens when :
(1) Ethanamide is heated with Br2 and aqueous
KOH ?
(2) Benzene diazonium chloride is treated with
Ethanol ?
 OR
(iii) Write short notes on the following :
(1) Carbylamine reaction
(2) Acetylation of aniline
A Answer ¥ Set 1, 4 Marks
(i) Methylamine, due to +I effect of methyl group.
(ii) Because of the absence of H-bonding in tertiary
amines.
(iii)(1) Methanamine or methylamine is formed.
(2) Benzene is formed.
OR
(iii)(1) On adding CHCl3 and alc. KOH in primary
amine, foul smelling isocyanide is formed.
(2) On adding CH3COCl-pyridine or
(CH3CO)2O, aniline gets acetylated to
acetanilide.
§ 2023 56/1/1 All Sets
š Question 17
CH3CONH2 on reaction with NaOH and Br2 in
alcoholic medium gives :
(a) CH3COONa (b) CH3NH2
(c) CH3CH2Br (d) CH3CH2NH2
A Answer ¥ Set 1, 1 Marks
(b) CH3NH2

š Question 18
Which of the following is least basic ?
(a) (CH3)2NH (b) NH3

NH2
(c) (d) (CH3)3N
A Answer ¥ Set 1, 1 Marks

NH2
(c)
 š Question 19
Assertion (A) : –NH2 group is o- and p-directing
in electrophilic substitution reactions.
Reason (R) : Aniline cannot undergo
Friedel-Crafts reaction.
(a) Both Assertion (A) and Reason (R) are true
and Reason (R) is the correct explanation of
the Assertion (A).
(b) Both Assertion (A) and Reason (R) are true,
but Reason (R) is not the correct explanation
of the Assertion (A).
(c) Assertion (A) is true, but Reason (R) is false.
(d) Assertion (A) is false and Reason (R) is also
false.
A Answer ¥ Set 1, 1 Marks
Both Assertion (A) and Reason (R) are true, but
Reason (R) is not the correct explanation of the
Assertion (A).
 š Question 20
Assertion (A) : Acetylation of aniline gives a
monosubstituted product.
Reason (R) : Activating effect of –NHCOCH3
group is more than that of amino group.
(a) Both Assertion (A) and Reason (R) are true
and Reason (R) is the correct explanation of
the Assertion (A).
(b) Both Assertion (A) and Reason (R) are true,
but Reason (R) is not the correct explanation
of the Assertion (A).
(c) Assertion (A) is true, but Reason (R) is false.
(d) Assertion (A) is false and Reason (R) is also
false.
A Answer ¥ Set 1, 1 Marks
(c) Assertion (A) is true, but Reason (R) is false.
š Question 21
Explain briefly :
(a) Carbylamine reaction (b) Gabriel phthalimide synthesis
A Answer (Either give explanation or reaction) ¥ Set 1, 2 Marks
(a) Aliphatic and aromatic primary amines on heating with chloroform
and ethanolic potassium hydroxide form isocyanides or carbylamines
which are foul-smelling substances. /
Heat
R–NH2 + CHCl3 + 3KOH −−→ R–NC+3KCl + 3H2O
Isocyanide with an offensive smell is formed.
(b) Phthalimide on treatment with ethanolic potassium hydroxide forms
potassium salt of phthalimide which further on heating with alkyl
halide followed by alkaline hydrolysis produces the corresponding
primary amine / (or it’s full reaction can also be written and can
skip it’s theory part.)
 ™ Question 22
Assertion (A) : (C2H5)2NH is more basic than
(C2H5)3N in aqueous solution.
Reason (R) : In (C2H5)2NH, there is more steric
hindrance and +I effect than (C2H5)3N.
(a) Both Assertion (A) and Reason (R) are true
and Reason (R) is the correct explanation of
the Assertion (A).
(b) Both Assertion (A) and Reason (R) are true,
but Reason (R) is not the correct explanation
of the Assertion (A).
(c) Assertion (A) is true, but Reason (R) is false.
(d) Assertion (A) is false, but Reason (R) is true.
A Answer ¥ Set 2, 1 Marks
Assertion (A) is true, but Reason (R) is false.

™ Question 23
Assertion (A) : Ammonolysis of alkyl halides is
not a suitable method for the preparation of pure
primary amines.
Reason (R) : Ammonolysis of alkyl halides yields
mainly secondary amines.
(a) Both Assertion (A) and Reason (R) are true
and Reason (R) is the correct explanation of
the Assertion (A).
(b) Both Assertion (A) and Reason (R) are true,
but Reason (R) is not the correct explanation
of the Assertion (A).
(c) Assertion (A) is true, but Reason (R) is false.
(d) Assertion (A) is false, but Reason (R) is true.
A Answer ¥ Set 3, 1 Marks
Assertion (A) is true, but Reason (R) is false.

™ Question 24
(a) Write the IUPAC name for the following
organic compounds:
CH3 N CH2CH3

(b) Complete the following :

Sn Br2
C6H5NO2 −−−−−→ A −−−−−→ B
HCl H2O

A Answer ¥ Set 3, 2 Marks

(a) N-Ethyl-N-methylaniline or
N-Ethyl-N-Methylbenzenamine
NH2 NH2
Br2 Br2
(b) A = B=

Br2
§ 2023 56/2 All Sets
™ Question 25
Among the following, which is the strongest base?

NH2
(a)
H3C NH2
(b)
CH2 NH2
(c)
O2 N NH2
(d)
A Answer ¥ Set 1, 1 Marks

CH2 NH2
 ™ Question 26
Give reasons :
(i) Aniline on nitration gives good amount of
m-nitroaniline, though – NH2 group is o/p
directing in electrophilic substitution reactions.
(ii) (CH3)2 NH is more basic than (CH3)3N in an
aqueous solution.
(iii) Ammonolysis of alkyl halides is not a good
method to prepare pure primary amines.

***
Write the reaction involved in the following :
(i) Carbylamine test
(ii) Gabriel phthalimide synthesis
A Answer ¥ Set 1, 5 Marks
(i) Aniline gets protonated and is deactivated /
Aniline 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.
 ***
(i) R–NH2 +CHCl3 +NaOH −→ RNC+3NaCl+H2O
(ii) This question was repeated in 2023-1

™ Question 27
When Benzene diazonium chloride reacts with
phenol, it forms a dye. This reaction is called
(a) Diazotisation reaction
(b) Condensation reaction
(c) Coupling reaction
(d) Acetylation reaction
A Answer ¥ Set 2, 1 Marks
(c) Coupling reaction
 ™ Question 28
Among the following, which has the highest value
of pKb ?

NH2
(a)

CH2 NH2
(b)

H3C NH2
(c)

O2 N NH2
(d)
A Answer ¥ Set 3, 1 Marks

O2 N NH2
§ 2023 56/3 All Sets
™ Question 29
Among the following, which is the strongest base?

H3C NH2
(a)

O2 N NH2
(b)

NH2
(c)

CH2 NH2
(d)
A Answer ¥ Set 1, 1 Marks

CH2 NH2
™ Question 30
Write the chemical equation involved in the following reactions :
(a) Carbylamine reaction
(b) Gabriel phthalimide synthesis
A Answer ¥ Set 1, 2 Marks
(a) R – NH2 + CHCl3 + 3KOH (alc.) −→ R – NC + 3KCl + 3H2O

(b)
™ Question 31
Write the structures of A, B and C in the following reactions :

COOH NH3 Br2 + NaOH NaNO2 + HCl

(i) −−→ A −−−−−−→ B −−−−−−−
◦
→
∆ 0C
KCN LiAlH4 HNO2
(ii) CH3CH2Br −−→ A −−−→ B −−−
◦
→ C
0C

A Answer ¥ Set 1, 3 Marks

+ –
CONH2 NH2 N2 Cl

(i) A = B= C=

(ii) A = CH3CH2CN B = CH3CH2CH2NH2 C = CH3CH2CH2OH

™ Question 32
Benzene diazonium chloride on hydrolysis gives :
(a) Phenol
(b) Chlorobenzene
(c) Benzene
(d) Aniline
A Answer ¥ Set 2, 1 Marks
(a) Phenol

™ Question 33
The reaction of ammonia with a large excess of
methyl chloride will yield mainly :
(a) methylamine
(b) dimethylamine
(c) tetramethylammonium chloride
(d) trimethylamine
A Answer ¥ Set 3, 1 Marks
(c) tetramethylammonium chloride
§ 2023 56/4 All Sets
™ Question 34
The reduction of ethanenitrile with sodium and
alcohol gives

(a) 1-aminopropane (c) Ethanoic acid

(b) 1-aminoethane (d) Ethanamide

A Answer ¥ Set 1, 1 Marks

(b) 1-aminoethane

™ Question 35
The action of nitrous acid on ethylamine gives
mainly

(a) ethyl nitrite (c) nitroethane

(b) ethyl alcohol (d) ethane

A Answer ¥ Set 2, 1 Marks

(b) ethyl alcohol
™ Question 36
When nitrobenzene is heated with tin and
concentrated HCl, the product formed is :

NH2
(a)
+ –
NH3 Cl
(b)

N N
(c)

Cl
(d)
A Answer ¥ Set 3, 1 Marks

NH2
(a)

™ Question 37
Assertion (A) : Monobromination of aniline can
be conveniently done by protecting the amino
group by acetylation.
Reason (R) : Acetylation decreases the
activating effect of the amino group.
(a) Both Assertion (A) and Reason (R) are true
and Reason (R) is the correct explanation of
the Assertion (A).
(b) Both Assertion (A) and Reason (R) are true,
but Reason (R) is not the correct explanation
of the Assertion (A).
(c) Assertion (A) is true, but Reason (R) is false.
(d) Assertion (A) is false, but Reason (R) is true.
A Answer ¥ Set 1, 1 Marks
Both Assertion (A) and Reason (R) are true and
Reason (R) is the correct explanation of the
Assertion (A).

™ Question 38
Case Based Question
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 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 character. Influence of
the number of hydrogen atoms at nitrogen atom
on the type of reactions and nature of products is
responsible for identification and distinction
between primary, secondary and tertiary amines.
Presence of amino group in aromatic ring
enhances reactivity of the aromatic amines. Aryl
diazonium salts provide advantageous methods
for producing aryl halides, cyanides, phenols and
arenes by reductive removal of the diazo group.
Answer the following questions :
(i) Arrange the following in the increasing order
of their pKb values in aqueous solution :



C2H5NH2, C2H5 2 NH, C2H5 3 N
(ii) Aniline on nitration gives a substantial amount
of m-nitroaniline, though amino group is o/p
directing. Why?
(iii) An aromatic compound A of molecular
formula C7H6O2 on treatment with aqueous
ammonia and heating forms compound B.
Compound B on heating with Br2 and aqueous
 KOH gives a compound C of molecular formula
C6H7N. Write the structures of A, B and C.
OR
Complete the following reactions giving main
products :
NH2

(1) + Br2 (aq) −→

+ –
N2 Cl

HBF4
(2) −−−−−−−−→
NaNO2 / Cu, ∆

A Answer ¥ Set 1, 4 Marks

(i) (C2H5)2NH < (C2H5)3N < C2H5NH2
(ii) Due to the protonation of aniline to form
anilinium ion which makes it deactivating and
meta-directing.

COOH
(iii) A =

CONH2
B=
 NH2
C=

OR
NH2
Br Br
(1)

Br
NO2

(2)
§ 2023 56/5 All Sets
™ Question 39
Amides can be converted into amines by the
reaction named
(a) Hoffmann degradation
(b) Ammonolysis
(c) Carbylamine
(d) Diazotisation
A Answer ¥ Set 2, 1 Marks
(a) Hoffmann degradation

™ Question 40
In the reaction
C6H5NH2 + CHCl3 + 3KOH → A + 3B + 3C
the product A is
(a) C6H5NC
(b) C6H5CN
(c) C6H5Cl
(d) C6H5NHCH3
A Answer ¥ Set 3, 1 Marks
(a) C6H5NC
 ™ Question 41
Which of the following would not be a good
choice for reducing nitrobenzene to aniline ?

(a) LiAlH4 (c) Fe and HCl

(b) H2/Ni (d) Sn and HCl
A Answer ¥ Set 1, 1 Marks
(a) LiAlH4

™ Question 42
(i) Draw the zwitter ion structure for sulphanilic
acid.
(ii) How can the activating effect of – NH2 group
in aniline be controlled ?
OR
(i) Complete the reaction with the main product
formed
+ –
N2 Cl

CH3CH2OH
−−−−−−→
(ii) Convert Bromoethane to Propanamine.
A Answer ¥ Set 1, 2 Marks
 +
NH3

(i)

–
SO3
(ii) Protecting /deactivating – NH2 group by acetylation or acylation.

OR

(i)
KCN H2
(ii) CH3CH2Br −−→ CH3CH2CN −→ CH3CH2CH2NH2
Ni

In Place of H2/Ni, LiAlH4 or Na(Hg) with C2H5OH can also be used.

 Theory Recap

Nitriles on reduction with lithium aluminium

hydride (LiAlH4) or catalytic hydrogenation
(H2 / Ni) or Na(Hg) with C2H5OH produce
primary amines. This reaction is used for ascent
of amine series, i.e., for preparation of amines
containing one carbon atom more than the
starting amine.
 ™ Question 43
(a) Illustrate Sandmeyer’s reaction with an
equation.
(b) Explain, why (CH3)2NH is more basic than
(CH3)3N in aqueous solution.
A Answer ¥ Set 1, 3 Marks
+ –
N2 Cl X

Cu2X2
(a) −−−→ + N2
HX

where X = Cl , Br , CN
(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.
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