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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1208

Succinic anhydride is treated with 1 equiv of aniline, then the product is heated strongly (dehydration). The final organic product is

  1. A1-phenylpyrrolidin-2-one
  2. B4-anilino-4-oxobutanoic acid
  3. CN1,N4-diphenylbutanediamide
  4. D1-phenylpyrrolidine-2,5-dione

Answer: D

Aniline opens the cyclic anhydride (carboxylate leaving group) to give the amide-acid 4-anilino-4-oxobutanoic acid. On strong heating the amide N attacks the CO2H group intramolecularly with loss of , closing a five-membered imide: 1-phenylpyrrolidine-2,5-dione.
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