Uploaded November 2021 | Updated September 2026, 2 weeks ago
The mechanism of the Feist-Bénary reaction involves an aldol reaction followed by an intramolecular O-alkylation and dehydration to yield the furan product. The starting material is deprotonated by the base to yield anion. This carbanion reacts with chloroacetaldehyde to furnish aldol adduct. Protonation of the alkoxide anion followed by deprotonation of the O dicarbonyl leads to formation of enolate. Dihydrofuran is produced by an intramolecular SN2 reaction between the oxygen nucleophile and the carbon bearing the chloride leaving group. The desired furan is then produced by dehydration via protonated intermediate.
Music: Cake – Mokka
The mechanism of the Feist-Bénary reaction involves an aldol reaction followed by an intramolecular O-alkylation and dehydration to yield the furan product. The starting material is deprotonated by the base to yield anion. This carbanion reacts with chloroacetaldehyde to furnish aldol adduct. Protonation of the alkoxide anion followed by deprotonation of the O dicarbonyl leads to formation of enolate. Dihydrofuran is produced by an intramolecular SN2 reaction between the oxygen nucleophile and the carbon bearing the chloride leaving group. The desired furan is then produced by dehydration via protonated intermediate.
Music: Cake – Mokka
