oxidation of alcohols

primary alcohol — “mild” oxidizers

aldehyde

primary alcohol — “strong” oxidizer

carboxylic acid

secondary alcohol — “mild” oxidizers

ketone

secondary alcohol — “strong” oxidizer

ketone

tertiary alcohol — “mild” oxidizers

no reaction

tertiary alcohol — “strong” oxidizer

no reaction

“mild” oxidizers

• PCC, CH₂Cl₂

• NaOCl, CH₃CO₂H, 0 C

• Swern Oxidation:

  1. (CH₃)₂SO, (COCl)₂, -60 C

  2. Et₃N

“strong” oxidizer

• H₂CrO₄ (Na₂Cr₂O₇, H₂SO₄ sometimes called “Jones Reagent” or “Jones Oxidation”)