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JEE Main levelSingle correct optionDifficulty 2 of 3el273

The sulpha drug shown is treated with one equivalent of acetic anhydride. Which structure shown is the main product, assuming only the more nucleophilic nitrogen reacts?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: B

The compound shown is sulphanilamide. The aromatic NH2 is far more nucleophilic than the sulphonamide NH2 (whose lone pair is delocalised onto SO2), so it is acetylated to give 4-acetamidobenzenesulphonamide. Other structures have the wrong site, no reaction or an N,N-diacetyl product.
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