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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3nc053

Which statements about the Hinsberg test are correct?

  1. A gives a sulfonamide that dissolves in aqueous alkali.
  2. B gives a sulfonamide that is insoluble in aqueous alkali.
  3. C gives a sulfonamide that dissolves in aqueous alkali.
  4. D gives a sulfonamide that is insoluble in aqueous alkali.

Answer: A, D

A primary amine gives with an acidic N-H, which forms a soluble sodium salt in alkali, whether the amine is aliphatic or aromatic, so aniline's sulfonamide dissolves. A secondary amine gives with no acidic hydrogen, which is insoluble. A tertiary amine does not form a sulfonamide at all.
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