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Chapter 12: Q26E (page 354)

Nonconjugated β,γ-unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated α,β-unsaturated isomers. Propose a mechanism for this isomerization.

Short Answer

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The mechanism of the given isomerization is

Mechanism

Step by step solution

01

Mechanism of the reaction

The mechanism of the given isomerization is

Mechanism

02

Explanation of the mechanism

The isomerization of 3-cyclohexanone to form 2-cyclohexanone takes place through the formation of its enol.

The acid protonates the carbonyl oxygen in the ketone. Then the partially positively charged hydrogen is abstracted, which forms the enol. Protonation of the enol with the electron pairs of oxygen yields a protonated 2-cyclohexenone. Lastly, deprotonation gives our desired product.

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