Oxidation of Alcohols and Aldehydes:

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Presentation transcript:

Oxidation of Alcohols and Aldehydes:

Many oxidative processes (e. g Many oxidative processes (e.g., benzylic, allylic, alicyclic, or aliphatic hydroxylation) generate alcohol or carbinol metabolites as intermediate products. If not conjugated, these alcohol products are further oxidized to aldehydes (if primary alcohols) or to ketones (if secondary alcohols).

Aldehyde metabolites resulting from oxidation of primary alcohols or from oxidative deamination of primary aliphatic amines often undergo facile oxidation to generate polar carboxylic acid derivatives. As a general rule, primary alcoholic groups and aldehyde functionalities are quite vulnerable to oxidation

Several drug examples in which primary alcohol metabolites and aldehyde metabolites are oxidized to carboxylic acid products are cited in sections above. Although secondary alcohols are susceptible to oxidation, this reaction is not often important because the reverse reaction, namely, reduction of the ketone back to the secondary alcohol, occurs quite readily. In addition, the secondary alcohol group, being polar and funclionalizcd, is more likely to be conjugated than the ketone moiety.