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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 (NHNH)! strong "ase (K#H or Na#H)! diethylene glycol ($% &'o)

solvent and high temerature (*+,o).

he mechanism /0t#H can "e relaced 1ithHOO

OH

O

NHNH

Na#H! 0t#H! ht

H2O

H H

N N

O

N

NH

H

H

H

-O

N+

N

H

H

H

H

Et

O

H

O-

N

N

H

H

H

Et

O+

H

H

or H#-or H#

O

N

N

H

H

HH

-O

N+

N

H

H

H

H

N

N

H

H O

HH

hydrazone

-O

H

N

N-

H

N- N

H

O

HH

or 0t#H

ketone

or aldehydehydrazine

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Wolff-Kishner Reduction Mechanisms

N N

H-O

H

H

NN

-

H

O

HH

2-2 leaving

grou

(uhill reaction "ut can

haen "3c hi and form

sta"le N)

C- N N

H

O

HH

H

H

-O

H

alkane

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