Which of the following alkyl bromides is likely to undergo rearrangement by a 1,2-methyl shift?
A)benzyl bromide
B)2-bromo-3-ethylpentane
C)3-bromo-3-methylpentane
D)2-bromo-3,3-dimethylpentane
E)3-bromo-2,3-dimethylpentane

Question

Quizplus · Accepted Answer

2-bromo-3,3-dimethylpentane is the only option that has a tertiary carbocation intermediate that can be stabilized by a 1,2-methyl shift. The other options either have primary (B and C) or secondary (A and E) carbocation intermediates that are less likely to undergo rearrangement.

Which of the Following Alkyl Bromides Is Likely to Undergo