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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

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

Karahanaenone, a terpenoid isolated from oil of hops, has been synthesized by the thermal reaction shown. Identify the kind of pericyclic reaction, and explain how karahanaenone is formed.

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.

Propose a pericyclic mechanism to account for the following transformation.

The following reaction is an example of a [2,3] sigmatropic rearrangement. Would you expect the reaction to be suprafacial or antarafacial? Explain.
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