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Chapter 27: Q 44. (page 1102)

Question: What type of sigmatropic rearrangement is illustrated in each reaction?

Short Answer

Expert verified

Answer

a. 1,5sigmatropic shift

b.2,3sigmatropic shift

Step by step solution

01

Sigmatropic shift

  • A sigmatropic rearrangement is an intramolecular pericyclic reaction.
  • The reactant鈥檚 蟽 bond is broken, and the蟺bonds rearrange to form a new bond in the product.
  • In a sigmatropic rearrangement, the number of 蟺 bonds is constant in the reactant and product
02

 [1,5] and [2,3] sigmatropic shifts

The 1,5sigmatropic shift is associated with the rearrangement of the group at the first and fifth positions.

The 2,3sigmatropic shift is associated with the rearrangement of the group at the second and third positions.

03

Explanation

a. In the given conversion, the groups at the first position rearrange themselves at the fifth position. Therefore, it is a 1,5sigmatropic shift.

b. In the given conversion, the groups at the second position rearrange themselves at the third position. Therefore, it is a 2,3 sigmatropic shift.

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