Ester Condensation: Claisen Reaction
Start with the big picture
A Claisen condensation begins when base removes an α-hydrogen from an ester to form an enolate. The enolate attacks a second ester carbonyl, and collapse of the tetrahedral intermediate expels an alkoxide, forming a β-keto ester. A subsequent deprotonation helps drive the reaction; acidic work-up then reprotonates the product. Reaction design matters: an alkoxide matching the ester’s OR group helps avoid trans-esterification, and at least one ester partner needs an α-hydrogen. The lesson also introduces crossed Claisen reactions, the intramolecular Dieckmann variant, and common limitations. Finally, it connects β-keto esters to further synthetic transformations, including alkylation and decarboxylation.
What you'll learn
- Describe the sequence of steps in the Claisen condensation mechanism.
- Explain why ester α-hydrogens and a matching alkoxide base matter.
- Distinguish intramolecular Dieckmann and selected crossed Claisen condensations.
- Identify key reaction limitations and synthetic uses of β-keto esters.
Continue your study
Work through the complete notes and reinforce the topic with the study tools available in the full lesson.