The amine shown reacts with benzenesulfonyl chloride and aqueous KOH to give a sulfonamide that is insoluble in the alkali. Which of the structures shown gives, under the same Hinsberg conditions, a sulfonamide that dissolves in KOH and is reprecipitated on acidification?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: C

In the Hinsberg test only a primary amine gives

RNHSO X_{2} Ph

with an acidic N-H, which dissolves in alkali as the sodium salt. The shown N-methylaniline is secondary (insoluble sulfonamide), A is secondary, B and D are tertiary (no sulfonamide). C (propylamine) is primary.

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