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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1205

Methyl 4-aminobutanoate is heated (neat, with removal of methanol). The organic product is

  1. Apyrrolidin-2-one
  2. B4-aminobutanoic acid
  3. Cazetidin-2-one
  4. Dpiperidin-2-one

Answer: A

The amine nitrogen attacks the ester carbonyl intramolecularly. Counting N, C4, C3, C2, C1 gives a five-membered ring, which forms rapidly (a strain-free ring with a favourable proximity effect). Methanol is lost, giving the lactam pyrrolidin-2-one.
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