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JEE Main levelSingle correct optionDifficulty 2 of 3co074

Diethyl hexanedioate is treated with one equivalent of NaOEt in ethanol and the mixture is then acidified (Dieckmann condensation). The product is

  1. Aethyl 2-oxocyclopentane-1-carboxylate
  2. Bethyl 2-oxocyclohexane-1-carboxylate
  3. Ccyclopentanone
  4. Ddiethyl cyclopentane-1,2-dicarboxylate

Answer: A

The ester enolate at C2 attacks the ester carbonyl at C6, forming a ring of C2 to C6, which is five-membered. Loss of ethoxide gives the cyclic beta-keto ester, ethyl 2-oxocyclopentane-1-carboxylate.
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