How can aldehydes and ketones be produced from alcohols?

1 Answer
Mar 12, 2016

By oxidation of the alcohol; usually you don't have to try too hard.

Explanation:

Primary alcohols, 1^@1 alcohols, R_1CH_2OHR1CH2OH oxidize to (i) the aldehyde, R_1C(=O)HR1C(=O)H, and then to the carboxylic acid, R_1CO_2HR1CO2H. Normally, it is hard to stop oxidation at the aldehyde.

Secondary alcohols, 2^@2 alcohols, R_1CH(OH)R_2R1CH(OH)R2, oxidize to give the ketone R_1C(=O)R_2R1C(=O)R2, and normally stop at this stage. Ketones tend to be a lot more robust under oxidative conditions.

Why should we want to make aldehydes and ketones? Well, they open the possibility of C-CCC bond formation with anionic carbon residues.

Tertiary alcohols, , 3^@3 alcohols, R_1C(OH)R_2R_3R1C(OH)R2R3, are inert to oxidation.