Many 1,2 diols, under the acidic conditions used for dehydration of alcohols, undergo a reaction called the pinacol rearrangement Propose a curved arrow mechanism for this reaction, and explain why the rearrangement step is energetically favorable OH OH IE CH3 CH3 H3C C C CH3 2,3 dimethyl 2,3 butan...

First analyze the connectivity changes that take place A methyl group shifts to an adjacent carbon a ...

Many 1,2-diols, under the acidic conditions used for dehydration of alcohols, undergo a reaction called the pinacol

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Many 1,2-diols, under the acidic conditions used for dehydration of alcohols, undergo a reaction called the pinacol rearrangement: OH OH IE CH3 CH3 H3C-C- -C-CH3 2,3-dimethyl-2,3-butanediol (pinacol) HSO4 CH3 HC-C- -C-CH3 + HO CH3

Propose a curved-arrow mechanism for this reaction, and explain why the rearrangement step is energetically favorable.

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Organic Chemistry

ISBN: 9781936221349

6th Edition

Authors: Marc Loudon, Jim Parise

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Question Posted: Jan 25, 2024 07:00 AM

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Many 1,2-diols, under the acidic conditions used for dehydration of alcohols, undergo a reaction called the pinacol

Question:

OH OH IE CH3 CH3 H3C-C- -C-CH3 2,3-dimethyl-2,3-butanediol (pinacol) HSO4 CH3 HC-C- -C-CH3 + HO CH3 3,3-dimethyl-2-butanone (pinacolone) (65-72% yield) (19.13)

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First analyze the connectivity changes that take place A methyl group shifts to an adjacent carbon a...View the full answer

Organic Chemistry

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