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Chapter 30: Q.30-17 (page 1033)

The following thermal rearrangement involves two pericyclic reactions in sequence. Identify them, and propose a mechanism to account for the observed result.

Short Answer

Expert verified

Mechanism is given as

Step by step solution

01

Reaction

The steps involved are

  1. 4 Membered Ring Opening
  2. 3 Membered Ring Opening(4+2 cycloaddition)
02

Mechanism

The mechanism can be represented as:

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Most popular questions from this chapter

Vinyl-substituted cyclopropanes undergo thermal rearrangement to yield cyclopentenes. Propose a mechanism for the reaction, and identify the pericyclic process involved.

The 1H NMR spectrum of bullvalene at 100 掳C consists only of a single peak at 4.22 d. Explain.

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.

Ring-opening of the trans-cyclobutene isomer shown takes place at much lower temperature than a similar ring-opening of the cis-cyclobutene isomer. Explain the temperature effect, and identify the stereochemistry of each reaction as either conrotatory or disrotatory.

Bicyclohexadiene, also known as Dewar benzene, is extremely stable despite the fact that its rearrangement to benzene is energetically favored. Explain why the rearrangement is so slow.
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