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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

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.

The 13C NMR spectrum of homotropilidene taken at room temperature shows only three peaks. Explain.

What product would you expect to obtain from the photochemical cyclizationof (2E,4Z,6E)-2,4,6-octatriene? Of (2E,4Z,6Z)-2,4,6-octatriene?

The cyclohexadecaoctaene shown isomerizes to two different isomers, depending on reaction conditions. Explain the observed results, and indicate whether each reaction is conrotatory or disrotatory.
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