Swern Oxidation

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

Visão geral

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.

Exemplo do cotidiano

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

Importância industrial

A oxidação de Swern é amplamente utilizada na química de processos farmacêuticos devido às suas condições suaves, seletividade e evitamento de metais pesados tóxicos.

Propriedades

Tipo: Organic
Reversível: Não
Energia: Exotérmico
ΔH: -120,0 kJ/mol

Reações relacionadas

Oxidation of Secondary Alcohol to Ketone Claisen Condensation (Ethyl Acetate) Kolbe Electrolysis Baeyer-Villiger Oxidation Beckmann Rearrangement (Cyclohexanone Oxime) Catalytic Hydrogenation of Ethylene Condensation Polymerization (Nylon 6,6) Cope Rearrangement Oxidation of Primary Alcohol to Aldehyde Epoxidation of Alkenes (mCPBA)

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.