3. Rearrangement Reactions (3/3)

Question 1

Indicate the rearrangement of the following cation.

Answer 1

Question 2

Give the mechanism for the following Pinacol rearrangement.

Answer 2

Question 3

Give the mechanism for the following Semi-Pinacol rearrangement.

Answer 3

Question 4

Give the mechanism for the following Wagner-Meerwein rearrangement.

Answer 4

Question 5

Provide the steps to generate:
1. Tertiary carbocation from olefin
2. Halonium cation from olefin
3. Activated epoxide/ carbocation from epoxide
4. Primary, secondary and tertiary carbocations from primary, secondary and tertiary alcohols

Answer 5

Question 6

For the following carbocation rearrangement, why is the migration from C6-C7 favoured?

Answer 6

Question 7

Answer 7

Question 8

Indicate the stereoselectivity in the following alkoxide fragmentation with alpha leaving group

Answer 8

Question 9

Indicate the stereoselectivity in the following alkoxide fragmentation with beta leaving group (E2).

Answer 9

Question 10

Answer 10

Question 11

Indicate the Favorskii reaction for:
1. Alkoxide with alpha leaving group
2. Alkoxide with beta leaving group

Answer 11

Question 12

Give the step and mechanism for the following Favorskii reaction.

Answer 12

Question 13

Draw curly arrows for all steps of the following mechanism.

Answer 13

Question 14

Draw curly arrows for all steps of the following mechanism.

Answer 14