Swern Oxidation

RCH2OH + (COCl)2 + DMSO → RCHO + DMS + CO2 + CO + 2HCl

Übersicht

The Swern oxidation converts primary and secondary alcohols to aldehydes and ketones using DMSO activated by oxalyl chloride, followed by base (triethylamine). It operates at -78 C (dry ice/acetone) to prevent side reactions. This mild, chromium-free method is preferred for sensitive substrates.

Alltägliches Beispiel

The Swern oxidation replaced toxic chromium reagents in many pharmaceutical syntheses, making drug manufacturing safer.

Industrielle Bedeutung

Swern oxidation is widely used in pharmaceutical process chemistry due to its mild conditions, selectivity, and avoidance of toxic heavy metals.

Eigenschaften

Typ
Organic
Reversibel
Nein
Energie
Exotherm
ΔH
-120,0 kJ/mol

Verwandte Reaktionen

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

Frequently Asked Questions

What is the equation for Swern Oxidation?
The balanced equation is: RCH₂OH + (COCl)₂ + DMSO → RCHO + DMS + CO₂ + CO + 2HCl.
What type of reaction is Swern Oxidation?
Swern Oxidation is a organic reaction.
Is Swern Oxidation exothermic or endothermic?
Swern Oxidation is exothermic (releases energy). The enthalpy change (ΔH) is -120.0 kJ/mol.