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15.26: Esters to β-Ketoesters: Claisen Condensation Overview

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Organic Chemistry

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Esters to β-Ketoesters: Claisen Condensation Overview

15.26: Esters to β-Ketoesters: Claisen Condensation Overview

Regular Claisen condensation is a base-promoted reaction involving identical esters with two α hydrogens, condensing to produce β-ketoesters. It is a nucleophilic acyl substitution reaction wherein one of the ester molecules, upon deprotonation by the base, forms a nucleophilic enolate ion, while the other molecule serves as an electrophile.


The condensation reaction requires specific nonaqueous bases, such as alkoxide, which must be similar to the alkoxy group of the ester molecule. The use of different alkoxide ions often leads to the transesterification product. Also, the use of hydroxide bases is avoided as they result in irreversible hydrolysis of the esters to carboxylate ions.



Esters β-Ketoesters Claisen Condensation Base-promoted Reaction Nucleophilic Acyl Substitution Ester Molecules Enolate Ion Electrophile Nonaqueous Bases Alkoxide Alkoxy Group Transesterification Product Hydroxide Bases Irreversible Hydrolysis Carboxylate Ions

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