Identification of Primary, secondary and tertiary amines

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Identification of Primary, Secondary, and Tertiary Amines

➤ Sulphonylation-Hinsberg Test

This test involves treatment with benzenesulphonyl chloride 

(Hinsberg reagent) 

or p-toluenesulphonyl chloride.

The reaction is used to 

separate a mixture of amines.

Primary (1°) and secondary 

(2°) amines, due to the 

presence of active hydrogen,

 react and give the corresponding sulphonamide, while tertiary

 (3°) amines do not react.

The product of a 1° amine, N-alkylbenzenesulphonamide,

 is soluble in KOH, forming a

 water-soluble salt.

➤ Nitrous Acid Test

A 1° amine reacts with 

HNO₂ to usually form 

an alcohol. This reaction

 involves the formation 

of a diazonium salt as 

an intermediate.

A 2° amine gives a nitrosoamine,

 which is a yellow oily liquid.

A 3° amine dissolves in cold 

HNO₂ to form an unstable

 salt that decomposes on

 heating to yield a nitrosoamine 

and an alcohol.

➤ Treatment with CS₂/HgCl₂

A 1° amine on warming with

 CS₂ produces dithiocarbamic

 acid, which decomposes

 by mercuric chloride to

 form an alkyl isothiocyanate. 

This is known as Hoffmann's

 Mustard Oil Reaction.

Although a 2° amine forms 

dithiocarbamic acid, it does

 not decompose by mercuric 

chloride.

A 3° amine does not react with CS₂.

➤ Carbylamine Reaction

A 1° amine, when treated 

with chloroform and alcoholic 

KOH, releases unpleasant or 

pungent vapors of alkyl 

carbylamine (isocyanide). 

This reaction is known as the 

Carbylamine Test and is specific for 1° amines.

➤ Aromatic Diazonium Salts

Aromatic diazonium salts are

 prepared by adding a cold

 aqueous solution of NaNO₂ 

in the presence of HCl at 273-278 K. 

This reaction is called diazotization.

Aromatic diazonium salts are much more stable than aliphatic diazonium salts due to the dispersal of positive charge on the benzene ring.

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