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Chemistry

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Organic Chemistry

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α-Carbon Chemistry: Enols, Enolates, and Enamines

Base Choice in Claisen Condensation

Description

Claisen condensation uses a base to join two identical esters that each have two alpha hydrogens. The reaction forms a beta-ketoester. It is a nucleophilic acyl substitution reaction.

In this reaction, the base removes an alpha hydrogen from one ester. That ester becomes a nucleophilic enolate io...

Transcript

Regular Claisen condensation is the reaction when identical ester molecules bearing two α hydrogens combine to generate a β-keto ester—a molecule comprising a keto group β to the ester group.

Claisen condensations require nonaqueous alkoxide bases to initiate the reaction by deprotonating the α hydrogen of the ester and producing the nucl...

Tags

Beta KetoestersEster ReactionNucleophilic Acyl SubstitutionEnolate Ion FormationAlkoxide BaseTransesterification ProductHydroxide Base AvoidanceCarbon Carbon Bond FormationOrganic Synthesis Mechanism