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Organic Synthesis

Formation

Mechanism: Carbonyl reduction, alcohol formation



Various reduction reactions can reduce aldehydes and ketones. Catalytic hydrogenation, lithium aluminum hydride, sodium borohydride, but not sodium cyanoborohydride. Tosylhydrazones followed by sodium cyanoborohydrides will reduce ketones/aldehydes to alcohols. For alpha/beta unsaturated carbonyls, the Luche reduction, with cerium borohydride (cerium chloride sesquihydrate plus sodium borohydride) will reduce the carboyl without the alpha/beta double bond. Hydrazine can reduce ketones to alkanes (Wolff-Kishner).



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