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Chapter 30: Q.30-19 (page 1033)

The following thermal isomerization occurs under relatively mild conditions. Identify the pericyclic reactions involved, and show how the rearrangement occurs.

Short Answer

Expert verified

The Conversion can be shown as

Step by step solution

01

Reaction

The steps involved are

  1. 1,5 sigmatropic rearrangement
  2. Rotation of bond
  3. 1,5 sigmatropic rearrangement
02

Mechanism

The whole mechanism can be represented as:

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Most popular questions from this chapter

trans-3,4-Dimethylcyclobutene can open by two conrotatory paths to give either (2E,4E)-2,4-hexadiene or (2Z,4Z)-2,4-hexadiene. Explain why both products are symmetry-allowed, and then account for the fact that only the 2E,4Eisomer is obtained in practice.

What stereochemistry would you expect for the product of the Diels鈥揂lder reaction between (2E,4E)-2,4-hexadiene and ethylene? What stereochemistry would you expect if (2E,4Z)-2,4-hexadiene were used instead?

The following rearrangement was devised and carried out to prove the stereochemistry of [1,5] sigmatropic hydrogen shifts. Explain how the observed result confirms the predictions of orbital symmetry.
  1. The following synthesis of dienones occurs readily. Propose a mechanism to account for the results, and identify the kind of pericyclic

reaction involved.

The cyclohexadecaoctaene shown isomerizes to two different isomers, depending on reaction conditions. Explain the observed results, and indicate whether each reaction is conrotatory or disrotatory.
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