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As I understand it (and please correct me if I'm wrong), ketones and aldehydes can be reduced to methylene derivatives via:

  • Clemmensen Reduction (acidic conditions):

enter image description here

  • Wolff-Kishner Reaction (basic conditions):

enter image description here

  • Mozingo Reaction (mild conditions)

enter image description here

A preference for Clemmensen or Wolff-Kishner can be established based on functional group tolerance with respect to acidic vs basic conditions.

But if the Mozingo Reaction doesn't have the drawback of requiring either acidic or basic conditions, is there a reason to ever use the Clemmensen Reduction or Wolff-Kishner Reaction instead of simply applying the Mozingo Reaction?

images for reaction formulas from their respective Wikipedia pages

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    $\begingroup$ The smell of the dithiane is a common issue. $\endgroup$ – NotEvans. Nov 4 '18 at 14:11
  • $\begingroup$ A good test of your handling skills. Hydrazine has H&S issues too. $\endgroup$ – Waylander Nov 4 '18 at 16:48
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    $\begingroup$ In monofunctional compounds it usually doesn’t matter. Multifunctional compounds require judicious choices. $\endgroup$ – user55119 Nov 6 '18 at 18:40

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