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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

Propose a pericyclic mechanism to account for the following transformation.

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.

Photolysis of the cis-cyclobutene isomer in Problem 30-35 yields cis-cyclododecaen-7-yne, but photolysis of the trans isomer yields trans-cyclododecaen-7-yne. Explain these results, and identify the type and stereochemistry of the pericyclic reaction.
  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 1H NMR spectrum of bullvalene at 100 °C consists only of a single peak at 4.22 d. Explain.
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