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Jones Oxidation

The Jones oxidation uses chromium trioxide (CrO3), acid, water, and acetone to convert 1° or 2° alcohols into carboxylic acids or ketones respectively. Chromic acid is first prepared by dissolving CrO3 or Cr2O72- in acid: the monomeric form (HCrO4-) dominating in dilute solutions versus the dimeric form (HCr2O7-) dominating in concentrated solutions. Alcohol makes a chromate ester with HCrO4-, eliminating HCrO3- to yield the carbonyl compound.

  • Reagents: Chromium Trioxide or Dichromate, Acid (e.g. Dilute Sulfuric Acid or Acetic Acid), Water, Acetone
  • Reactant: 1° Alcohol (Alkyl, Aryl, Alkenyl) or 2° Alcohol (Alkyl, Aryl)
  • Product: Carboxylic Acid or Ketone
  • Type of Reaction: Oxidation
Mechanism
Original Paper
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