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JEE Main levelSingle correct optionDifficulty 2 of 3nc253

The amine shown is treated with benzenesulfonyl chloride and excess aqueous (Hinsberg test). What is observed?

  1. AA clear solution forms because an alkali-soluble sulfonamide results
  2. BAn insoluble sulfonamide separates from the alkali
  3. CA diazonium salt is formed
  4. DNo sulfonamide is formed; the amine is recovered unchanged and dissolves in dilute acid

Answer: D

The compound shown is triethylamine, a tertiary amine. It has no N-H and cannot form a stable sulfonamide, so the amine remains unreacted (the sulfonyl chloride is hydrolysed by alkali). The amine is then recovered and dissolves in dilute HCl.
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