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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3nc200

Which statements about the Hinsberg test (benzenesulfonyl chloride, then aqueous alkali) are correct?

  1. AA primary amine gives an N-alkylbenzenesulfonamide that dissolves in alkali.
  2. BA secondary amine gives a sulfonamide that is insoluble in alkali.
  3. CA tertiary amine does not give a sulfonamide.
  4. DThe sulfonamide formed from a secondary amine dissolves in alkali because it has an acidic N-H.

Answer: A, B, C

Only a sulfonamide with an N-H attached to the sulfonyl group is acidic enough to dissolve in alkali (primary amines). Secondary amines give N,N-disubstituted sulfonamides with no N-H, insoluble in alkali; tertiary amines have no N-H to lose and do not form sulfonamides.
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