Reaction of an alcohol with thionyl chloride in the presence of a tertiary amine (e.g.
Chapter 11, Problem 11.55(choose chapter or problem)
Reaction of an alcohol with thionyl chloride in the presence of a tertiary amine (e.g., pyridine) affords replacement of the OH group by Cl with inversion of configuration (Section 11.9). However, if the amine is omitted, the result is usually replacement with retention of configuration. The same chlorosulfite intermediate is involved in both cases. Suggest a mechanism by which this intermediate can give the chlorinated product without inversion.
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