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Question
Account for the following:
On reaction with benzene sulphonyl chloride, primary amine yields product soluble in alkali whereas secondary amine yields product insoluble in alkali.
Solution
The reaction of benzene sulphonyl chloride with 1o amine yields N-ethylbenzene sulphonyl amide.
The hydrogen attached to nitrogen in sulphonamide is strongly acidic due to the presence of electron with drawing sulphonyl group and the reaction with 2° amine, N, N-diethyl benzene sulphonamide is formed.
Since N, N-diethylbenzene sulphonamide does not conains any hydrogen atom attached to nitrogen atom, it is not acidic and hence insoluble in alkali.
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