Chem 203: Organic Chemistry II - Ester Enolates and Conjugate Addition

These flashcards cover key concepts related to ester enolates, Claisen condensations, conjugate additions, and related organic chemistry reactions.

Claisen Condensation

A reaction involving the formation of a β-keto ester through the nucleophilic acyl substitution of esters.

Ester Enolate

A nucleophilic species formed from an ester when a proton is removed from its alpha carbon.

Conjugate Addition

A reaction where nucleophiles add to α,β-unsaturated carbonyl compounds, yielding 1,4-addition products.

Dieckmann Cyclization

An intramolecular Claisen condensation that results in the formation of cyclic β-ketoesters.

Michael Reaction

A conjugate addition reaction where a nucleophile attacks a Michael acceptor, typically an α,β-unsaturated carbonyl compound.

Nucleophilic Acyl Substitution

A mechanism where a nucleophile attacks a carbonyl carbon, leading to substitution of a leaving group.

Decarboxylation

The process of removing a carboxyl group from a molecule, typically involving the loss of carbon dioxide.

Aldol Reaction

A reaction in which aldehydes or ketones react to form β-hydroxy aldehydes or ketones when combined with enolates.

Stork Enamine Synthesis

A method of synthesizing carbonyl compounds using enamines as stable nucleophilic intermediates.

Intramolecular Claisen Condensation

A Claisen condensation where the nucleophile and electrophile are parts of the same molecule, forming a ring.