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Swern Oxidation Reagents

Swern Oxidation Reagents ((COCl)₂ + DMSO + Et₃N) - oxidizing reagent. Mild oxidation of alcohols to aldehydes/ketones. Common uses: 1° Alcohol → Aldehyde, 2° Alcohol → Ketone. No heavy metals. Very mild. Done at -78°C. Smelly byproduct (dimethyl sulfide).

Oxidizing

Reagent details

Name

Swern Oxidation Reagents

Formula

(COCl)₂ + DMSO + Et₃N

Category

Oxidizing

Function

Mild oxidation of alcohols to aldehydes/ketones

Common Uses

  1. 1° Alcohol → Aldehyde

  2. 2° Alcohol → Ketone

Notes

No heavy metals. Very mild. Done at -78°C. Smelly byproduct (dimethyl sulfide).

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Reagents

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DIBAL-H

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Lindlar Catalyst (Pd/CaCO₃/Pb) - reducing reagent. Partial reduction of alkynes to cis-alkenes. Common uses: Alkyne → cis-Alkene (stops at alkene). Poisoned catalyst - lead prevents over-reduction. Syn addition gives cis product.

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Dissolving Metal (Na/NH₃) (Na + NH₃(l)) - reducing reagent. Reduction of alkynes to trans-alkenes. Common uses: Alkyne → trans-Alkene. Birch reduction conditions. Liquid ammonia at -33°C. Radical mechanism gives trans product.

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