Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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9.

CH3
CH3
The Wolff-Kishner reaction involves the reaction of an aldehyde/ketone with hydrazine in the presence of KOH. The process is useful for converting an aldehyde or ketone into an alkane. The reaction involves formation of a hydrazone,
followed by base-catalyzed double-bond migration, loss of N₂ gas to give a carbanion, and protonation to give the alkane.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
n
Ph
Ph
:0:
↔XT
H₂NNH₂
KOH
CH3
HẲN NH,
Ph
Ph
:0:
-CH₂CH₂CH3
HẸN NH2
+ N₂ + H₂O
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Transcribed Image Text:CH3 CH3 The Wolff-Kishner reaction involves the reaction of an aldehyde/ketone with hydrazine in the presence of KOH. The process is useful for converting an aldehyde or ketone into an alkane. The reaction involves formation of a hydrazone, followed by base-catalyzed double-bond migration, loss of N₂ gas to give a carbanion, and protonation to give the alkane. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions n Ph Ph :0: ↔XT H₂NNH₂ KOH CH3 HẲN NH, Ph Ph :0: -CH₂CH₂CH3 HẸN NH2 + N₂ + H₂O
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