Question

Write the mechanism for the following reaction.

2-methyl-2-propanol + HBr 2-bromo-2-methylpropane​

Answer 1

Answer:

In questions 2 and 3, only the proton trans to the leaving group can eliminate.

CH3

D

3)

H

CH3

4) Due to the presence of the bulky t-butyl group, the ring is practically locked up in the most

stable conformation with the bulky group being equatorial.

t-Bu

H

t-Bu = t-Butyl group

Br

H

t-Bu

H

H

Br

cis trans

Of the two isomers, the cis is the only one that fulfills the anticoplanar arrangement for E2, where

the leaving group and adjacent proton must be anti to each other and in the same plane.

Explanation: