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The Clemmensen reduction uses amalgamated zinc (Zn/Hg) and hydrochloric acid to reduce an aldehyde or ketone to an alkane. Two proposed mechanisms exist: the “Carbanionic mechanism” involves zinc directly attacking the carbonyl group and the formation of carbanion intermediates, while the “Carbenoid mechanism” occurs on the surface of zinc, involving a radical intermediate and zinc carbenoid.
- Reagents: Zn(Hg), Organic Solvent (e.g. Toluene), HCl (40% aq.)
- Reactant: Aldehyde or Ketone
- Product: Alkane
- Type of Reaction: Reduction
- Clemmensen Reduction of Ketones in Anhydrous Organic Solvents. In Organic Reactions; American Cancer Society, 2011; pp 401–422.
- One-Pot Reductive Cleavage of Exo-Olefin to Methylene with a Mild Ozonolysis-Clemmensen Reduction Sequence. Tetrahedron Letters 2010, 51 (34), 4534–4537.
- Wolff-Kishner Reduction
- Corey-Bakshi-Shibata Reduction
- Zn Catalyst
- HCl (CAS 7647-01-0)