Organic Chemistry / Carbocation Intermediate Rearrangements
Sign up for free to keep watching this solution

Video Solution: In Problem 5.20 (Section 5.13) we saw that acid-catalyzed de...

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. 

 

Related Practice Problems

When compound shown below is exposed to an acid, a molecule of water is elimin...

When compound shown below is exposed to an acid, a molecule of water is elimin...

Provide a detailed mechanism for the following transformation. Show all charge...

Provide a detailed mechanism for the following transformation. Show all charge...

Draw the full mechanism for this reaction including rearrangements if pos...

Draw the full mechanism for this reaction including rearrangements if pos...

There is no carbocation rearrangement in reactions where a bridged intermediat...

There is no carbocation rearrangement in reactions where a bridged intermediat...

Which carbocation would not be likely to undergo rearrangement?
...

Which carbocation would not be likely to undergo rearrangement? ...