Wolff kishner reduction, Organic and heterocyclic chemistry, As per PCI sylllabus
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The Wolff-Kishner reduction is a chemical reaction that reduces ketones or aldehydes to hydrocarbons. It involves refluxing the carbonyl compound with hydrazine and a strong base like sodium hydroxide or potassium hydroxide. This causes the carbonyl group to be reduced to a methylene group, forming the corresponding hydrocarbon. The reaction proceeds through formation of a hydrazone intermediate that is deprotonated and collapsed to lose dinitrogen and form an alkylanion, which is then protonated to yield the reduced product. This reduction method is advantageous over other methods as it avoids the use of strongly acidic conditions that could cause side reactions.
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- 2. Wolff Kishner reduction NH2NH2 RCOR’ -------------- RCH2R’ Alcohol/Base • Ketones and aldehydes on reduction with base gives corresponding hydrocarbons. The reaction is carried out heating the hydrocarbon of aldehyde and ketone in presence of NaOH or KOH
- 3. • The related reduction of aldehyde and ketone to H/C is carried out by refluxing the carbonyl comp with amalgamated zinc and HCl. The condition employed in this method is strongly acidic and may give rise to side chain reaction. • The hydrazone is deprotonated by alkoxide base followed by a concerted, rate-determining step in which a diimide anion is formed. Collapse of this alkyldiimide with loss of N2 leads to formation of an alkylanion which can be protonated by solvent to give the desired product
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