The amine shown is treated with benzenesulfonyl chloride and aqueous alkali (Hinsberg test). Which observation is correct?

AA sulfonamide forms with no N-H, so it is insoluble in alkali
BA sulfonamide forms with an N-H, so it dissolves in alkali
CNo reaction occurs because the amine is secondary
DThe sulfonamide dissolves in alkali only after acidification

Answer: A

The compound shown is N-methylbenzylamine, a secondary amine. It gives an N,N-disubstituted sulfonamide, which has no hydrogen on nitrogen and so cannot form a soluble sodium salt; it remains insoluble in alkali.

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