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Reduction of Carbonyl Groups to Methylene Groups

Wolff-Kishner Reduction: Mechanism

The Wolff-Kishner reduction consists of four reaction steps.

Fig.1
Step 1

Step 1: Conversion of ketone to hydrazone with hydrazine (reaction of carbonyl with base)

Fig.2
Step 2

Step 2: Base-catalyzed tautomerisation of hydrazone to an azo derivative

Fig.3
Step 3

Step 3: E2-elimination with formation of N2 and carbanion

Fig.4
Step 4

Step 4: Protonation of the carbanion

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