1° alcohol: PCC (pyridinium chlorochromate, mild) -> aldehyde (stops here). K2Cr2O7/H2SO4 or KMnO4 -> carboxylic acid (over-oxidation). Jones reagent (CrO3/H2SO4/acetone) -> acid. 2° alcohol: Any oxidant -> ketone (no further oxidation without C-C cleavage). 3° alcohol: Resistant to oxidation under normal conditions. Under vigorous conditions, C-C bond cleaves to give mixture of acids/ketones. Catalytic dehydrogenation: Cu/573 K: 1° -> aldehyde + H2; 2° -> ketone + H2; 3° -> alkene + H2O (dehydration, not dehydrogenation). Oppenauer oxidation: 2° alcohol + acetone (Al(OiPr)3) -> ketone + isopropanol (reverse of Meerwein-Ponndorf-Verley).
Part of JOC-05 — Alcohols, Phenols & Ethers
Reactions of Alcohols — Oxidation
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