Question

If the temperature is not kept below $25^{\circ} \mathrm{C}$ during the reaction of primary alcohols with $p$ -toluenesulfonyl 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.

Name: If the temperature is not kept below 25^∘C during the reaction of primary alcohols with p -toluenesulfonyl 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.
Uploaded: 2022-04-02T22:43:19-08:00
Duration: 1 min 38 s
Channel: Grigoriy Sereda
Description: If the temperature is not kept below 25^∘C during the reaction of primary alcohols with p -toluenesulfonyl 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.

          If the temperature is not kept below $25^{\circ} \mathrm{C}$ during the reaction of primary alcohols with $p$ -toluenesulfonyl 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.

Added by Jesus C.

Organic Chemistry

Janice Gorzynski Smith 4th Edition

Instant Answer

Solved by Expert Grigoriy Sereda

04/02/2022

Step 1

The desired product is an alkyl $ p $-toluenesulfonate. This reaction typically involves the formation of a sulfonate ester, where the alcohol acts as a nucleophile and attacks the sulfonyl chloride, displacing the chloride ion. Show more…

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If the temperature is not kept below $25^{\circ} \mathrm{C}$ during the reaction of primary alcohols with $p$ -toluenesulfonyl 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.