Master Organic Chemistry Reaction Guide

Pinacol Rearrangement

Description: The Pinacol rearrangement involves the shift of an alkyl group accompanied by loss of water and the conversion of an alcohol to a ketone (or aldehyde).

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Real-Life Examples:

Org. Synth. 1925, 5, 91

DOI Link: 10.15227/orgsyn.005.0091

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Org. Synth. 1934, 14, 12

DOI Link: 10.15227/orgsyn.014.0012

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7 thoughts on “Pinacol Rearrangement

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  3. In an example where the two alcohols are bound to carbon atoms with differing substitutions, the more substituted alcohol will attack. This must be due to electron density differences within the molecule correct? The more substituted alcohol is made more negative in being bound to a carbon that is less negative?

    1. The more substituted alcohol is the one more likely to ionize and form a free carbocation. The alkyl group that migrates is more likely to come from the less substituted carbon.

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