MolSynapsequestion bank
MolSynapse / Question bank / Aldehydes, Ketones and Carboxylic Acids / Aldol, Cannizzaro, Perkin, Claisen and related condensations
JEE Main levelSingle correct optionDifficulty 2 of 3co076

Ethyl benzoate and ethyl ethanoate are treated with NaOEt, with ethyl ethanoate added slowly to the mixture of ethyl benzoate and base (crossed Claisen condensation), followed by acidification. The main product is

  1. Aethyl 3-oxobutanoate
  2. B1-phenylbutane-1,3-dione
  3. Cethyl 3-oxo-3-phenylpropanoate
  4. Dethyl 3-hydroxy-3-phenylpropanoate

Answer: C

Ethyl benzoate has no alpha-hydrogen and can only be the electrophile. The enolate of ethyl ethanoate attacks it and ethoxide is lost. The product is . Slow addition keeps ethyl ethanoate low, suppressing self-condensation to ethyl 3-oxobutanoate.
Practice Aldehydes, Ketones and Carboxylic Acids More on Aldol, Cannizzaro, Perkin, Claisen and related condensations
Previous questionNext question

More questions on Aldol, Cannizzaro, Perkin, Claisen and related condensations