Question: If the temperature is not kept below 25C during the reaction of primary alcohols with ptoluenesulfonyl chloride in pyridine, it is sometimes observed that the

If the temperature is not kept below 25°C during the reaction of primary alcohols with ptoluenesulfonyl chloride 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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