Spring 2009. Dr. Halligan CHM 236. Chapter 12. Oxidation and Reduction. 1. 1. Introduction. Recall that oxidation results in an increase in the number of C—Z bonds (usually C—O bonds) or a decrease in the number of C—H bonds.
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Oxidation and Reduction
A general scheme for the
oxidation and reduction of
a carbon compound
Oxidation and reduction of
Write some examples of oxidation and reduction reactions.
the double bonds
in a vegetable oil
Summary: Three methods to
reduce a triple bond
Examples of reduction of C – X
σ bonds with LiAIH4
Oxidation reactions of alkenes,
alkynes, and alcohols
The synthesis of disparlure
Blood alcohol screening
Dimethylsulfoxide, oxalyl chloride and triethylamine are used to oxidize 1° and 2° alcohols to aldehydes and ketones.
Notice that the 1° alcohol stops at the aldehyde since there is no water involved in this reaction.
DMSO reacts with oxalyl chloride to form dimethyl-chlorosulfonium ion which is the species used to oxidize the alcohol.
Triethylamine abstracts a hydrogen to produce the carbonyl.
Write a mechanism for the Swern Oxidation of benzyl alcohol to benzaldehyde.