Textbook Question
Propose a mechanism for the crossed Claisen condensation between ethyl acetate and ethyl benzoate.
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25. Condensation Chemistry
Claisen Condensation
Multiple Choice
Draw the structure of the Claisen condensation product for each of the following compounds.
A
B
C
D
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Verified step by step guidance1
Identify the reactants: The reaction involves an ester and a ketone. The ester is ethyl benzoate, and the ketone is methyl acetate.
Understand the reaction conditions: The reaction is a Claisen condensation, which requires a strong base (NaOMe) and an alcohol (MeOH) as a solvent.
Deprotonation step: The base (NaOMe) deprotonates the alpha hydrogen of the ester, generating an enolate ion.
Nucleophilic attack: The enolate ion attacks the carbonyl carbon of the other ester molecule, forming a tetrahedral intermediate.
Elimination step: The intermediate collapses, expelling the methoxide ion (OMe-) and forming a β-keto ester as the Claisen condensation product.
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