Swern Oxidation

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

Overview

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.

Everyday Example

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

Industrial Importance

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

Properties

Type: Organic
Reversible: No
Energy: Exothermic
ΔH: -120.0 kJ/mol

Related Reactions

Aldol Condensation of Acetaldehyde Amide Formation (Acetic Acid + Ammonia) Baeyer-Villiger Oxidation Beckmann Rearrangement (Cyclohexanone Oxime) Bromination of Ethylene Buchwald-Hartwig Amination Cannizzaro Reaction of Formaldehyde Catalytic Hydrogenation of Ethylene Claisen Condensation (Ethyl Acetate) Condensation Polymerization (Nylon 6,6)

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.