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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

When a 2,6-disubstituted allyl phenyl ether is heated in an attempted Claisen rearrangement, migration occurs to give the p-allyl product as the result oftwo sequential pericyclic reactions. Explain.

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