Wolff-Kishner Reduction Mechanisms

Wolff-Kishner Reduction of an aldehyde or ketone results in an alkane (and nitrogen gas) via a
hydrazone intermediate.
Requires hydrazine (NH2NH2), strong base (KOH or NaOH), diethylene glycol (BP 245 oC)
solvent and high temperature (180oC).
O

The mechanism *EtOH can be replaced with HO

O

OH

NH 2NH2

H
H 2O

NaOH, EtOH, ht

H
H
H
N

ketone
or aldehyde

-O

N+

H
H

hydrazine

O
Et

or H 2O

H
O

O
N

Et

or HO

H
H

O-

N
N

O
H

N+

-O
H

hydrazone

-O
H

H
N
-

NN

O
H

or EtOH

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Wolff-Kishner Reduction Mechanisms

H
N

-O

H
N

N-

"C-" leaving
group
(uphill reaction but can
happen b/c hi T and form
stable N2)
O
H
H

-O
H

C-

alkane

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