The Swern oxidation oxidizes primary alcohols to aldehydes
Chapter 11, Problem 71(choose chapter or problem)
The Swern oxidation oxidizes primary alcohols to aldehydes and secondary alcohols to ketones using dimethyl sulfoxide and oxalyl chloride, followed by reaction with triethylamine. The actual oxidizing agent is the dimethylchlorosulfonium ion, (CH 3 ) 2S + Cl. (To see how this compound is formed from the reactants, see in Chapter 17 .) Propose a mechanism for the oxidation. ( Hint: the i rst step is an S N 2 reaction, the last step is an E2 reaction.)
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