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Question

Which of the following amines will form a product that is soluble in KOH, on reaction with Hinsberg’s reagent?

A
Isopropylamine
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B
N,N-Dimethylaniline
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C
Aniline
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D
Diethylamine
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Solution

The correct option is C Aniline
Primary amines on reacting with Hinsberg's reagent gives benzene sulphonamide which has acidic proton attached to N atom and is soluble in alkali like KOH.
Here, isopropylamine and aniline are primary amines.
Thus, reaction of Hinsberg’s reagent with Isopropylamine and aniline gives N-isopropylbenzene sulphonamide and N-phenylbenzene sulphonamide respectively. The lone hydrogen attached to the N atom is strongly acidic due to the presence of strong electron withdrawing sulphonyl group. Hence, they are soluble in alkali like KOH.
Hence, option (a) and (c) are correct.

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