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Chapter 30: Q.30-19 (page 1033)

The following thermal isomerization occurs under relatively mild conditions. Identify the pericyclic reactions involved, and show how the rearrangement occurs.

Short Answer

Expert verified

The Conversion can be shown as

Step by step solution

01

Reaction

The steps involved are

  1. 1,5 sigmatropic rearrangement
  2. Rotation of bond
  3. 1,5 sigmatropic rearrangement
02

Mechanism

The whole mechanism can be represented as:

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Most popular questions from this chapter

Bicyclohexadiene, also known as Dewar benzene, is extremely stable despite the fact that its rearrangement to benzene is energetically favored. Explain why the rearrangement is so slow.

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.

Heating (1Z,3Z,5Z)-1,3,5-cyclononatriene to 100°C causes cyclization and formation of a bicyclic product. Is the reaction conrotatory or disrotatory? What is the stereochemical relationship of the two hydrogens at the ring junctions, cis or trans?

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.

The following reaction is an example of a [2,3] sigmatropic rearrangement. Would you expect the reaction to be suprafacial or antarafacial? Explain.
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