Baeyer-Villiger Oxidation

R2CO + RCO3H → R2CO2 (ester or lactone)

Übersicht

A peracid oxidizes a ketone by inserting an oxygen atom between the carbonyl carbon and an adjacent carbon, converting the ketone to an ester or lactone. The more substituted group migrates preferentially (migratory aptitude). This reaction is named after Adolf von Baeyer and Victor Villiger who discovered it in 1899.

Alltägliches Beispiel

The Baeyer-Villiger oxidation is used in the synthesis of caprolactone, the monomer for biodegradable polycaprolactone used in medical sutures.

Industrielle Bedeutung

Caprolactone production by Baeyer-Villiger oxidation of cyclohexanone supports the biodegradable plastic and medical device industries.

Eigenschaften

Typ
Organic
Reversibel
Nein
Energie
Exotherm
ΔH
-180,0 kJ/mol

Verwandte Reaktionen

Epoxidation of Alkenes (mCPBA) Swern Oxidation Oxidation of Secondary Alcohol to Ketone E2 Elimination (Dehydrohalogenation) Claisen Condensation (Ethyl Acetate) Aldol Condensation of Acetaldehyde Kolbe Electrolysis Beckmann Rearrangement (Cyclohexanone Oxime) Catalytic Hydrogenation of Ethylene Dehydration of Ethanol

Frequently Asked Questions

What is the equation for Baeyer-Villiger Oxidation?
The balanced equation is: R₂CO + RCO₃H → R₂CO₂ (ester or lactone).
What type of reaction is Baeyer-Villiger Oxidation?
Baeyer-Villiger Oxidation is a organic reaction.
Is Baeyer-Villiger Oxidation exothermic or endothermic?
Baeyer-Villiger Oxidation is exothermic (releases energy). The enthalpy change (ΔH) is -180.0 kJ/mol.