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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

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.

Photolysis of the cis-cyclobutene isomer in Problem 30-35 yields cis-cyclododecaen-7-yne, but photolysis of the trans isomer yields trans-cyclododecaen-7-yne. Explain these results, and identify the type and stereochemistry of the pericyclic reaction.

Look at Figure 30-1, and tell which molecular orbital is the HOMO and whichis the LUMO for both ground and excited states of ethylene and 1,3-butadiene.

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.


Ring-opening of the trans-cyclobutene isomer shown takes place at much lower temperature than a similar ring-opening of the cis-cyclobutene isomer. Explain the temperature effect, and identify the stereochemistry of each reaction as either conrotatory or disrotatory.
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