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Also known as: Chromic Acid Oxidation, Jones Reagent
A strong Cr(VI) oxidation that converts primary alcohols all the way to carboxylic acids and secondary alcohols to ketones. Cannot stop at the aldehyde stage for primary alcohols (use PCC or Swern for that).
The alcohol forms a chromate ester with CrO₃ under acidic conditions.
An E2-like elimination removes the α-hydrogen and breaks the Cr-O bond, giving the carbonyl product and Cr(IV). Cr(IV) is further reduced to Cr(III) (green).
Color change: orange Cr(VI) → green Cr(III)
For primary alcohols: the aldehyde intermediate is hydrated in aqueous conditions, and the hydrate is oxidized again to carboxylic acid.
Aqueous conditions prevent stopping at aldehyde
1-Butanol
CrO₃/H₂SO₄/acetone
Butanoic acid
Cyclohexanol
Jones reagent
Cyclohexanone
Reliable oxidation of secondary alcohols to ketones. Also useful when carboxylic acid (not aldehyde) is desired from primary alcohols.