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MolSynapse / Question bank / Aldehydes, Ketones and Carboxylic Acids / Aldol, Cannizzaro, Perkin, Claisen and related condensations
JEE Advanced levelOne or more correct optionsDifficulty 3 of 3co105

Which diesters give a five- or six-membered cyclic beta-keto ester as the main product when treated with one equivalent of NaOEt in ethanol (Dieckmann condensation)? (One or more answers)

  1. Adiethyl butanedioate
  2. Bdiethyl pentanedioate
  3. Cdiethyl hexanedioate
  4. Ddiethyl heptanedioate

Answer: C, D

The enolate carbon C2 attacks the ester carbonyl at the other end, forming a ring that contains all carbons from C2 to the terminal carbonyl carbon. Butanedioate and pentanedioate would give rings of 3 and 4, which are strained. Hexanedioate gives 5 and heptanedioate gives 6.
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