ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
10th Edition
ISBN: 9781259972348
Author: Carey
Publisher: MCG CUSTOM
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Chapter 6, Problem 29P

If the temperature is not kept below 25 o C during the reaction of primary alcohols with p-toluenesulfonylchloride in pyridine, it is sometimes observed that the isolated product is not the desired alkyl p-toluenesulfonate but is instead the corresponding alkyl chloride. Suggest a mechanistic explanation for this observation.

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