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Chapter 20
4th Edition
Paula Yurkanis Bruice More About
Oxidation–Reduction
Reactions
Irene Lee
Case Western Reserve University
Cleveland, OH
©2004, Prentice Hall
• Oxidation is always coupled with reduction
Ozonide is stable
Ozonides can be cleaved to carbonyl compounds
Examples of the Oxidative Cleavage of
Alkenes by Ozonolysis
A peroxyacid, OsO4, and (cold basic) KMnO4 break only
the p bond of the alkene
Ozone and acidic KMnO4 break both the p bond and the
s bond
Table 20.1 Summary of the Methods Used to Oxidize an Alkene
Oxidative Cleavage of Alkynes
O O
KMnO 4
CH3C CCH2CH3 CH3C CCH2CH3
HO -
O O
CH3C O3 +
CCH2CH3 CH3COH CH3CH2COH
H2O
O
O3
CH3CH2CH2C CH CH3CH2CH2COH + CO2
H2O
Conversion of an Aldehyde into Other
Functional Groups
Conversion of a Ketone into
an Ester or an Alcohol
Biological Oxidation–Reduction
Reactions
NAD+ oxidizes ethanol by accepting a hydride ion
NADH reduces a carbonyl compound by donating a
hydride ion