It is not particularly effective with alicyclic and aliphatic ketones and such acid-labile molecules should be reduced using the complementary Wolff-Kishner reaction.
The Haworth phenanthrene synthesis can utilize two of these reactions, and pinacol(*) formation can often be observed during this reaction. This process has been employed to reduce vanillin compounds using toluene as an auxiliary solvent to yield creosol. It can be used to convert a Friedel-Crafts acylation product to an alkyl side-chain, and requires the use of amalgamated zinc which functions in part as a metal activation surface. It is not particularly effective with alicyclic and aliphatic ketones and such acid-labile molecules should be reduced using the complementary Wolff-Kishner reaction. For 10 points, identify this chemical process requiring a strong acid substrate which allows for the deoxygenation of aldehydes or ketones to produce hydrocarbons.
The Haworth phenanthrene synthesis can utilize two of these reactions, and pinacol(*) formation can often be observed during this reaction.
Clemmensen reduction (accept Wolf-Kishner until *)