Reaction 7. Reduction of carbonyl groups of aldehydes and ketones to the methylene group (deoxygenation?)

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Purpose

convert carbonyl group to methylene

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Reagents and conditions

Zn/Hg/H+ for all aldehydes and ketones (Clemmensen)

H₂NNH₂/KOH/D for all aldehydes and ketones (Wolff- Kishner)

H2/Pd/C for aromatic ketones

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Mechanistic details

the Clemmensen reductions involves zinc amalgam under acidic conditions (complex mechanism)
the Wolf-Kishner reduction proceeds via hydrazone (the imine derived from the hydrazine, H₂NNH₂) and involves a carbanion intermediates.
the catalytic reduction is applicable only to aromatic ketones

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