Dr.

Caroline Clower
Chemistry 2411
Carbocation Rearrangement Key

Each of the following carbocations can rearrange via a hydride shift and/or a methyl shift. Draw
the most stable carbocation structure that will result from a rearrangement.

CH3 CH3

(a) H3C C CH2 H3C C CH2

H H

CH3 CH3

(b) H3C C CH CH3 H3C C CH CH3

CH3 CH3

CH3 CH3

(c) H3C C CH2 H3C C CH2

CH3 CH3

H H

(d) H C CH2 H C CH2

CH3 CH3

CH3 CH3

(e) CH3 CH2 C CH2 CH3 CH2 C CH2

H H

CH3 CH3

(f) H3C C CH CH2 H3C C CH CH2

H H H H