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Chapter 30: Q29E (page 1033)

Propose a pericyclic mechanism to account for the following transformation.

Short Answer

Expert verified

The pericyclic mechanism for the following transformation can be proposed.

Step by step solution

01

Sigma tropic rearrangement

The reaction is [3,3] sigma tropic rearrangement. There is an involvement of 3 electron pairs in the reaction. Thus, it is under thermal conditions through the suprafacial pathway to produce an enol. The enol was then tautomerized to produce ketone.

02

Cyclic mechanism for the transformation

The cyclic mechanism can be drawn as,

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Most popular questions from this chapter

The following reaction takes place in two steps, one of which is a cycloaddition while the other is a reverse cycloaddition. Identify the two pericyclic reactions, and show how they occur.

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.

Vinyl-substituted cyclopropanes undergo thermal rearrangement to yield cyclopentenes. Propose a mechanism for the reaction, and identify the pericyclic process involved.
  1. The following synthesis of dienones occurs readily. Propose a mechanism to account for the results, and identify the kind of pericyclic

reaction involved.

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.
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