CHE 232

Carbonyl and alcohol interconversions

The chart below shows the "forest" of alcohol and carbonyl interconversions. Alcohols are in column 1, ketones and aldehydes in column 2, and carboxylic acid derivatives in column 3. Row 1 involves primary alcohols and compounds to which they can be oxidized, row 2 involves secondary alcohols and compounds to which they can be oxidized, and row 3 involves tertiary alcohols.

Essentially, you can move "east" with oxidizing agents (PCC or Jones reagent), you can move "west" with reducing agents (NaBH4 and LiAlH4), and you can move "southwest" with C-based nucleophiles (e.g., Grignard reagents, enolates, arenes). You may not move directly in any other direction.

All of the carboxylic acid derivatives are interconvertible with one another, but some are appropriate starting materials for westward or southwestward reactions, whereas others are not.

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