CAREY: ORGANIC CHEMISTRY
CAREY: ORGANIC CHEMISTRY
10th Edition
ISBN: 9781260364002
Author: VALUE EDITION
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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