In the group shown below, which of the following alcohols is (are) likely to yield a product where skeletal rearrangement has occurred when treated with sulfuric acid?
3-methyl-3-pentanol, 3,3-dimethyl-2-butanol, 2,2-dimethylcyclohexanol
A) 3-methyl-3-pentanol only
B) 3,3-dimethyl-2-butanol only
C) 2,2-dimethylcyclohexanol only
D) both 3,3-dimethyl-2-butanol and 2,2-dimethylcyclohexanol
E) None of these three alcohols is prone to rearrangement.

Question

Quizplus · Accepted Answer

Both 3,3-dimethyl-2-butanol and 2,2-dimethylcyclohexanol are likely to undergo skeletal rearrangement when treated with sulfuric acid. This is because they both have a tertiary carbocation intermediate that can undergo rearrangement to form a more stable carbocation. 3-methyl-3-pentanol does not have a tertiary carbocation intermediate and therefore is not prone to skeletal rearrangement.

In the Group Shown Below, Which of the Following Alcohols