CHM 211, Assignment 6, MM 45

Q1. Provide an arrow pushing mechanism explaining how the following carbocation
rearrangements occur. (Hint: Number the carbon atoms to follow the trail) (5 x 4)

(a)
Hint: BF3 opens up the acetal and generates a carbocation

(b)
Hint: OMs is a good leaving group

(c)
Hint: mCPBA produces an unstable epoxide that rearranges to the product

(d)

Q2. Explain the following anionic rearrangements. (5 x 4)

(a)

(b)
 (c)

(d)

Q3. Provide a mechanism for the following reaction. CDI is carbonyl diimidazole: (5)