Hand-Out Chemistry

Chapter: Amines

MOHAMMED.ILIAS @55721312

Derivatives of ammonia
Obtained by the replacement of one, two or all the three H-atoms of ammonia by alkyl and/or aryl
groups

Nomenclature of Aliphatic Amines

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Hand-Out Chemistry
Chapter: Amines

MOHAMMED.ILIAS @55721312

Classify the following amines as primary, secondary or tertiary:

Primary
Secondary
Primary

Tertiary

Write IUPAC names of the following compounds and classify them into primary,secondary
and tertiary amines
(i) (CH3)2 CHNH2

(ii) CH3(CH2)2NH2 (iii) CH3NHCH(CH3)2

Propan-2-amine
(10 amine)

Propan-1-amine
(10 amine)

(v) C6H5NHCH3

(vi) (CH3CH2)2NCH3

(vii) mBrC6H4NH2

N-methylaniline
(20 amine)

N-Ethyl-N-methylethanamine
(30 amine)

3-bromoaniline (10 amine)

NMethyl,Propan-2-amine
(20 amine)

(iv) (CH3)3CNH2

-Methylpropan-2-amine (10
amine)

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Hand-Out Chemistry
Chapter: Amines

MOHAMMED.ILIAS @55721312

(i) Write structures of different isomeric amines corresponding to the molecular formula, C4H11N.
(ii) Write IUPAC names of all the isomers.
(iii) What type of isomerism is exhibited by different pairs of amines? (HOME WORK)

Methods of Preparation of Amines

By reduction of nitro compounds
Nitro compounds are reduced to amines by H2/Ni , H2/Pd , H2/Pt and Sn/HCl , Fe/HCl

CONVERT
a) Nitrobenzene to Aniline
b) Chloroethane to Ethanamine

Ammonolysis of alkyl halides

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 CX bond by ammonia molecule isknown as ammonolysis.

The disadvantage of this method is that

Ammonolysis does not give a single amine but mixture of amines
Aryl amines can not be prepared as low reactivity towards nucleophlic substitution

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Hand-Out Chemistry
Chapter: Amines

MOHAMMED.ILIAS @55721312

Write chemical equations for the following reactions:

a) Reaction of ethanolic NH3 with C2H5Cl.
b) Ammonolysis of benzyl chloride and reaction of amine so formed with two moles of CH3Cl.

Gabriel Pthalimide Synthesis

Gabriel synthesis is used for the preparation of primary amines. Phthalimide on treatment with ethanolic
potassium hydroxide forms potassium salt of phthalimide which on heating with alkyl halide followed by
alkaline hydrolysis produces the corresponding primary amine.

Aromatic primary amines cannot be prepared by this process.

Reason Aryl halides do not undergo nucleophilic substitution with the anion formed by phthalimide

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Hand-Out Chemistry
Chapter: Amines

MOHAMMED.ILIAS @55721312

Reduction of Nitrites
Reduction of nitrites with LiAlH4

Catalytic hydrogenation of nitriles

Reduction of amides

By Hoffmann bromamide degradation reaction: Primary amines can be prepared from amides by treatment with Br2
and KOH. Amine contains one carbon atom less than the parent amide

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