2.4 Me HCI(aq) Me

World of Chemistry, 3rd edition
3rd Edition
ISBN:9781133109655
Author:Steven S. Zumdahl, Susan L. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan L. Zumdahl, Donald J. DeCoste
Chapter10: Energy
Section: Chapter Questions
Problem 4A
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Propose a mechanism for the reaction in
Question 2.4

2.4
Me
HOI
HC(aq)
HO,
Me
Transcribed Image Text:2.4 Me HOI HC(aq) HO, Me
Expert Solution
Step 1

The given reaction is an example of Pinacol-Pinacolone rearrangement of 1,2-diol. The mechanism of the reaction involves five steps. The first step of the given reaction is protonation of one of the -OH group of diol. The second step is loss of H2O to generate a tertiary carbocation. The third step is migration of methyl group and thereby generation of new carbocation.

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