CLEMMENSEN REDUCTION
The Clemmensen Reduction involves adding ##”Zn(Hg)”## dissolved in heated ##”HCl”## to something reducible. Note though that this process can accidentally chlorinate a double bond also present on the reactant.
The principal action of the Clemmensen Reduction is to reduce a ##-stackrel(“O”)stackrel(||)”C”-## to a ##-“CH”_2-## or ##-stackrel(“O”)stackrel(||)”C”-“H”## to a ##-“CH”_3##.
So, using it on 2-butenal is supposed to turn it into 2-butene.
But when you have ##”HCl”##, a strong acid, in the presence of a double bond, there’s a good chance it’ll protonate the double bond. At that point a hydrochlorination would happen across the double bond, forming an alkyl chloride.
That’s why if you wanted to remove the carbonyl oxygen, you should do a similar reduction in basic media, and the Wolff-Kischner reduction qualifies.
WOLFF-KISHNER REDUCTION
The basic counterpart to the acidic Clemmensen reduction is the Wolff-Kishner reduction, which is run in base. It aims to accomplish the same thing, but in different, sometimes more favorable conditions.
The general reactants are hydrazine (##”H”_2″N”-“NH”_2##) and a strong base, like ##”NaOH”##.
WOLFF-KISHNER VS. CLEMMENSEN
The main benefit of the Wolff-Kishner reduction is that because it’s in base, it wouldn’t accidentally protonate a hydroxyl group or double bond in the reactant and allow side reactions to occur for acid-sensitive reagents.
Confer with a reaction involving a hydroxyaldehyde reactant (Organic Chemistry, Bruice, Ch. 15.18), and you would see the following conundrum is resolved by choosing one reduction method over the other:
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