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Chapter 30: Q.30-17 (page 1033)

The following thermal rearrangement involves two pericyclic reactions in sequence. Identify them, and propose a mechanism to account for the observed result.

Short Answer

Expert verified

Mechanism is given as

Step by step solution

01

Reaction

The steps involved are

  1. 4 Membered Ring Opening
  2. 3 Membered Ring Opening(4+2 cycloaddition)
02

Mechanism

The mechanism can be represented as:

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Most popular questions from this chapter

1,3-Cyclopentadiene reacts with cycloheptatrienone to give the productshown. Tell what kind of reaction is involved, and explain the observed result.Is the reaction suprafacial or antarafacial?

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.

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

Coronafacic acid, a bacterial toxin, was synthesized using a key step that involves three sequential pericyclic reactions. Identify them, and propose a mechanism for the overall transformation. How would you complete the synthesis?[pk1]

[pk1]Size should be 12 not 11.


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.
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