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Chapter 30: Q36E (page 1033)

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.

Short Answer

Expert verified

Photolysis of cis-cyclobutene isomer occurs in disrotatory manner in photochemical conditions while that of trans- cyclobutene isomer occurs in conrotatory manner.

Step by step solution

01

Photolysis of the cis-Cyclobutene Isomer

Photolysis of cis-cyclobutene isomer occurs in a disrotatory manner in photochemical conditions, as shown below:

02

Photolysis of the trans-Cyclobutene Isomer

Photolysis of trans-cyclobutene isomer occurs in conrotatory manner in photochemical conditions, as shown below:

trans-Cyclododecaen-7-yne

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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.

The 1H NMR spectrum of bullvalene at 100 掳C consists only of a single peak at 4.22 d. Explain.

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.

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

Which of the following reactions is more likely to occur? Explain.
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