Question

What does the oxidation of a primary alcohol produce?

Answer 1

Aldehydes, and then carboxylic acids.

Explanation:

Consider the formal oxidation numbers of the ipso carbon in `RCH_2OH`, `RC(=O)H`, and `RC(=O)OH`. The oxidation number of the ipso carbon, the carbon directly bound to oxygen, is `-I, +I,` and `+III` respectively. When carbon is fully oxidized it is `+IV`.

When a primary alcohol is oxidized it is often hard to get it to stop at the aldehyde. Careful monitoring by `"TLC"` or the use of some highly regioselective oxidation reagent is necessary to stop the oxidation at the aldehyde stage rather than at the carboxylic acid.