Concept explainers
Interpretation:
The structure of a
Concept Introduction:
During pinacol re-arrangement, a diol is converted to a ketone.
The reaction begins by protonation of one of the hydroxyl groups.
The loss of hydroxyl group produces initial carbocation. The initial carbocation results in the most stable carbocation.
In the next step, the water molecule departs, and an alkyl group from the adjacent carbon atom migrates to its position.
A new carbocation is created, where the hydroxyl group is attached to the carbon bearing the positive charge.
The unshared electrons pair on this hydroxyl group stabilizes the carbocation.
The final step is the formation of a carbonyl group and abstraction of a proton from the oxygen atom.
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Organic Chemistry - Standalone book
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning