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Chapter 17: Q17-68E (page 567)

2,3-Dimethyl-2,3-butanediol has the common name pinacol. On heating with aqueous acid, pinacol rearranges to pinacolone, 3,3-dimethyl-2-butanone. Suggest a mechanism for this reaction.

Short Answer

Expert verified

The mechanism of 2,3-dimethyl-2,3-butanediol (pinacol) rearranges to 3,3-dimethyl-2-butanone (pinacolone) as;

Step by step solution

01

Pinacol-pinacolone reaction is the conversion of the 1,2-diol compound to the corresponding carbonyl compound.

Pinacol-pinacolone reactionis the conversion of the 1,2-diol compound to the corresponding carbonyl compound. The following steps are completed by the reaction;

Protonation of one of the alcohol groups.

Removal of a water molecule (leaving group) to generate a carbocation.

The above-formed carbocation will be rearranged to give a more stable carbocation by migrating a group (in the given case, the methyl group will migrate from the adjacent carbon to form a stable carbocation) which further rearranges to give the corresponding carbonyl compound.

02

Mechanism of 2,3-dimethyl-2,3-butanediol (pinacol) rearranges to 3,3-dimethyl-2-butanone (pinacolone)

Consider the mechanism of 2,3-dimethyl-2,3-butanediol (pinacol) rearranges to 3,3-dimethyl-2-butanone (pinacolone) as;

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