Carbocation Intermediate Rearrangements Video Lessons

Concept: Understanding why carbocations shift.

# 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.

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###### Problem Details

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.

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Our tutors rated the difficulty ofIn Problem 5.20 (Section 5.13) we saw that acid-catalyzed de...as high difficulty.

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Our expert Organic tutor, Chris took 5 minutes and 39 seconds to solve this problem. You can follow their steps in the video explanation above.

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Based on our data, we think this problem is relevant for Professor Cruz's class at USF.

What textbook is this problem found in?

Our data indicates that this problem or a close variation was asked in Organic Chemistry - Carey 8th Edition. You can also practice Organic Chemistry - Carey 8th Edition practice problems.