2. Rearrangement Reactions (2/3)

Question 1

Give the generalised mechanism for the Favorskii rearrangement.

Answer 1

Question 2

Give the generalised mechanism for the Curtius rearrangement.

Answer 2

Question 3

Outline the resonance required for this Curtius rearrangement of acyl azide.

Answer 3

Question 4

Outline the products of the following reactions and complete the series with the relevant Curtius rearrangement and products.

Answer 4

Question 5

Answer 5

Question 6

Give the steps and mechanism for the formation of an acyl azide from carboxylic acid with DPPA (diphenylphosphoryl azide).

Answer 6

Question 7

What are the similarities between the Curtius and Hofmann rearrangements?

Answer 7

Question 8

Indicate the leaving group and step to form the isocyanate in the following Hofmann rearrangements.

Answer 8

Question 9

Answer 9

Question 10

Compare the stereochemistry for Beckmann, Baeyer-Villiger, Curtius and Hofmann rearrangements during 1,2-migration

Answer 10

Question 11

Give the generalised mechanism for the Wolff rearrangement.

Answer 11

Question 12

Provide the mechanisms for the Wolff rearrangement in the following Arndt-Eisert homologation by Wolff rearrangement.

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

Question 15

Draw curly arrows for all steps of the following mechanism.

Answer 15