Ph NH CH3 H-OH Ph N=NH H CH3 OH

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter17: Aldehydes And Ketones
Section: Chapter Questions
Problem 17.73P: 17-73 Alcohols can be prepared by the acid-catalyzed hydration of alkenes (Section 12-6B) and by the...
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9.

Ph
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.
NA
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
Ph
→XT
NH
ha
CH3
H₂NNH₂
KOH
H-OH
Ph
Ph
H
NH
CH3
+ N₂ + H₂O
OH
Transcribed Image Text:Ph 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. NA Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Ph →XT NH ha CH3 H₂NNH₂ KOH H-OH Ph Ph H NH CH3 + N₂ + H₂O OH
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