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Chapter 30: Q28E (page 1033)

Predict the product of the following pericyclic reaction. Is this [5,5] shift a suprafacial or an antarafacial process?

Short Answer

Expert verified

The product of the following pericyclic reaction can be predicted.

Step by step solution

01

Statement for pericyclic reaction

The pericyclic reaction can be given as a thermal [5,5] sigmatropic rearrangement reaction. There is an involvement of five electron pairs in the reaction. It takes place through the suprafacial pathway.

02

Product of the pericyclic reaction

The pericyclic reaction’s product can be shown as,

It is a suprafacial process for thermal [5,5] sigmatropic rearrangement.

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Most popular questions from this chapter

Vinyl-substituted cyclopropanes undergo thermal rearrangement to yield cyclopentenes. Propose a mechanism for the reaction, and identify the pericyclic process involved.

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.

What stereochemistry—antarafacial or suprafacial—would you expect to observe in the following reactions?

(a) A photochemical [1,5] sigmatropic rearrangement

(b) A thermal [4 + 6] cycloaddition

(c) A thermal [1,7] sigmatropic rearrangement

(d) A photochemical [2 + 6] cycloaddition

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?

Two sequential pericyclic reactions are involved in the following furan synthesis. Identify them, and propose a mechanism for the transformation.
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