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Chapter 22: Q36E (page 752)

Heating carvone with aqueous sulfuric acid converts it into carvacrol. Propose a mechanism for the isomerization.

Short Answer

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Step by step solution

Reaction process

In the process, the carvone is treated with aqueous sulfuric acid which produces carbocation intermediate. Then, the carbocation undergoes 1,2-Hydride shift and aromatization to produce Carvacol.

Mechanism

The mechanism for the reaction is,

Mechanism of the reaction

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Most popular questions from this chapter

The two optically beta-keto acids below were decarboxylated using the conditions typically used for the acetoacetate synthesis. Will the ketone products also be optically active? Provide the complete mechanism to explain your answer.