What does the oxidation of a primary alcohol produce?

1 Answer
anor277
May 12, 2016

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.

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