Can someone help me identify the steps for the following reaction? I'd like to keep track of everything that happens. I can't figure out what happens with oxidation in this context, and thus can't get started.

It's 2-methylpropan-1-ol oxidized with potassium dichromate(VI) in aqueous sulfuric acid to yield 2-methylpropanoic acid (also known as isobutyric acid).

Reaction schematic


1 Answer 1


A dichromate salt and aqueous sulfuric acid are used to prepare chromic acid in situ, which is among the most powerful oxidizing agents commonly available. A primary alcohol is first oxidized to an aldehyde (via a chromate ester intermediate). Under acidic conditions, the aldehyde's oxygen acts as a base and abstracts a proton, the carbonyl carbon is attacked by water (whose oxygen acts as a nucleophile) and simultaneously the carbonyl π-bond breaks, and then finally the resulting molecule is deprotonated by another water molecule, yielding a diol. That diol is then subject to further oxidation by the remaining chromic acid, which occurs by the same mechanism as the initial oxidation to an aldehyde. The ultimate result is a carboxylic acid.


Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.