Wolff-Kishner Reduction

Overall Reaction:
$$\text{R--CO--R'} + \text{NH}_2\text{NH}_2 \xrightarrow{\text{KOH / Ethylene glycol}, \, 453\text{--}473\text{ K}} \text{R--CH}_2\text{--R'} + \text{N}_2\uparrow + \text{H}_2\text{O}$$

Concept: Complete conversion of a carbonyl group into a hydrocarbon utilizing a basic hydrazine mechanism. The reaction forms an intermediate hydrazone that breaks down upon heating with a strong base, making this method entirely unsuitable for molecules containing base-labile groups (like alkyl halides or esters).

Notation:

• $$\text{NH}_2\text{NH}_2$$ = Hydrazine;
• $$\text{Ethylene glycol}$$ = High-boiling protic solvent required to safely reach necessary cracking temperatures.