Question:

An amine on reaction with benzensulphonyl chloride produces a compound insoluble in alkaline solution. This amine can be prepared by ammonolysis of ethyl chloride. The correct structure of amine is :

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An alkali-insoluble sulphonamide (Hinsberg test) means a secondary amine, and it should contain ethyl group(s) from ethyl chloride.
Updated On: Nov 4, 2026
  • \(\mathrm{CH_3CH_2NH_2}\)
  • \(\mathrm{CH_3CH_2CH_2NHCH_3}\)
  • \(\mathrm{CH_3CH_2CH_2-NH-CH_2CH_3}\)
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The Correct Option is C

Solution and Explanation

Hinsberg test: a primary amine gives a sulphonamide soluble in alkali (it has an acidic N-H); a secondary amine gives a sulphonamide insoluble in alkali; a tertiary amine does not react. So the amine is secondary.
Primary amine CH3CH2NH2 (option 1) is therefore ruled out.
Ammonolysis of C2H5Cl gives amines with only ethyl groups on N. Of the secondary amines given, option (2) has a CH3 group and option (4) is N-propylaniline with a phenyl group, neither of which can arise from ethyl chloride.
Option (3) is the secondary amine containing an ethyl group on nitrogen and is the best choice.
Answer: (3) CH3CH2CH2-NH-CH2CH3
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