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Question

Describe a method for the identification of primary, secondary and tertiary amines. Also, write chemical equations of the reactions involved.

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Solution

Hinsberg's test is used for the identification of primary, secondary, and tertiary amines.
Hinsberg's reagent is benzenesulphonyl chloride (C6H5SO2Cl).
It reacts differently with primary, secondary, and tertiary amines.
(i) Hinsberg's reagent reacts with primary amines to form N alkylbenzenesulphonyl amide which is acidic in nature and soluble in alkali.
Note: N alkylbenzenesulphonyl amide contains a strong electron-withdrawing sulphonyl group. Due to this, the H atom attached to nitrogen can be removed easily. Hence, it is acidic.
(ii) Hinsberg's reagent reacts with secondary amines to form a sulphonamide which is insoluble in alkali.
Note: As there is no hydrogen atom attached to the N atom in the sulphonamide, it is not acidic and insoluble in alkali.
(iii) Hinsberg's reagent does not react with tertiary amines.
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