Organic Chemistry Practice Problems Carbocation Intermediate Rearrangements Practice Problems Solution: In Problem 5.20 (Section 5.13) we saw that acid-ca...

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Solution: In Problem 5.20 (Section 5.13) we saw that acid-catalyzed dehydration of 2,2- dimethylcyclohexanol afforded 1,2-dimethylcyclohexene. To explain this product we must write a mechanism for the reaction in which a methyl shift transforms a secondary carbocation to a tertiary one. Another product of the dehydration of 2,2-dimethylcyclohexanol is isopropylidenecyclopentane. Write a mechanism to rationalize its formation, using curved arrows to show the flow of electrons.   

Problem

In Problem 5.20 (Section 5.13) we saw that acid-catalyzed dehydration of 2,2- dimethylcyclohexanol afforded 1,2-dimethylcyclohexene. To explain this product we must write a mechanism for the reaction in which a methyl shift transforms a secondary carbocation to a tertiary one. Another product of the dehydration of 2,2-dimethylcyclohexanol is isopropylidenecyclopentane. Write a mechanism to rationalize its formation, using curved arrows to show the flow of electrons.