Swern Oxidation

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

Descripción general

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.

Ejemplo cotidiano

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

Importancia industrial

Método suave y selectivo para oxidar alcoholes primarios a aldehídos sin sobreoxidación, ampliamente utilizado en síntesis total.

Propiedades

Tipo: Organic
Reversible: No
Energía: Exotérmico
ΔH: -120,0 kJ/mol

Reacciones relacionadas

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.