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AcetoAcetic Ester
AcetoAcetic Ester
Mechanism
A strong base deprotonates the dicarbonyl á-carbon. This carbon is preferred over the methyl
carbon because the formed enolate is conjugated, and thus resonance stabilized. The carbon then
undergoes nucleophilic substitution. When heated with aqueous acid, the newly alkylated ester
is hydrolyzed to a â-keto acid, which is decarboxylated to form a methyl ketone.