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Chapter 28: Q40P (page 1239)

cis-3,4-Dimethylcyclobutene undergoes thermal ring opening to form the two products shown. One of the products is formed in 99% yield, the other in 1% yield. Which is which?

Short Answer

Expert verified

Under thermal conditions, the conrotation ring closing is the major product. The conrotation ring-closing can take place when the substituents are cis to each other, that means are in the same direction as shown below:

Step by step solution

01

Conrotatory ring closure

Under thermal conditions, the conrotation ring closing is the major product. The conrotation ring-closing can take place when the substituents are cis to each other, that means are in the same direction as shown below:

02

Disrotatory ring closure

The disrotatory ring-closing under thermal conditions is minor product. In disrotatory ring-closing, the substituents are trans to each other as shown below:

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Most popular questions from this chapter

Explain why maleic anhydride reacts rapidly with 1,3-butadiene but does not react at all with ethene under thermal conditions.

A student found that heating any one of the isomers shown here resulted in scrambling of the deuterium to all three positions on the five-membered ring. Propose a mechanism to account for this observation.

Problem:Give a molecular orbital description for each of the following:

a. 1,3-pentadiene b. 1,4-pentadiene c. 1,3,5-heptatriene d. 1,3,5,8-nonatetraene

If isomer A is heated to about 100 °C, a mixture of isomers A and B is formed. Explain why there is no trace of isomer C or D.

Problem:a. Under thermal conditions, will ring closure of (2E,4Z,6Z,8E)-2,4,6,8-decatetraene be conrotatory or disrotatory?

b. Will the product have the cis or the trans configuration?

c. Under photochemical conditions, will ring closure be conrotatory or disrotatory?

d. Will the product have the cis or the trans configuration?
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