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
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Join thousands of students who trust us to help them ace their exams!Watch the first videoMultiple Choice
Draw the structure of the Claisen condensation product for each of the following compounds.
A
B
C
D
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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