Jones oxidation

[1] Jones reagent is a solution prepared by dissolving chromium trioxide in aqueous sulfuric acid.

To effect a Jones oxidation, this acidic mixture is then added to an acetone solution of the substrate.

These esters can be isolated when the alcohol is tertiary because these lack the α hydrogen that would be lost to form the carbonyl.

[5] For those structures with hydrogen alpha to the oxygen, the chromate esters degrade, releasing the carbonyl product and an ill-defined Cr(IV) product: The deuterated alcohols HOCD2R oxidize about six times slower than the undeuterated derivatives.

This large kinetic isotope effect shows that the C–H (or C–D) bond breaks in the rate-determining step.

[2][7] A variety of spectroscopic techniques, including Infrared spectroscopy, can be used to monitor the progress of a Jones oxidation reaction.