MolSynapsequestion bank
MolSynapse / Question bank / General Organic Chemistry III: Reaction Intermediates / Carbanions and enolates
JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g3081

Which of the following esters, when treated with one equivalent of in ethanol followed by acidification, give a self-condensation (Claisen) product in good yield? (The overall reaction is driven by deprotonation of the beta-keto ester product.)

  1. AEthyl benzoate
  2. BEthyl ethanoate
  3. CEthyl propanoate
  4. DEthyl 2-methylpropanoate

Answer: B, C

A Claisen condensation needs an ester with alpha hydrogen, and the beta-keto ester product must retain an acidic hydrogen between the two carbonyls so that the final deprotonation drives the equilibrium. Ethyl ethanoate and ethyl propanoate both give such products. Ethyl 2-methylpropanoate gives a product whose central carbon is quaternary (no acidic H), and ethyl benzoate has no alpha H at all.
Practice General Organic Chemistry III: Reaction Intermediates More on Carbanions and enolates

More questions on Carbanions and enolates