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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

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

a. Name the kind of sigmatropic rearrangement that occurs in each of the following reactions.

b. Using arrows, show the electron rearrangement that takes place in each reaction.

Propose a mechanism for the following reaction:

Problem:Which of the following are correct? Correct any false statements.

a. A conjugated diene with an even number of double bonds undergoes conrotatory ring closure under thermal conditions.

b. A conjugated diene with an antisymmetric HOMO undergoes conrotatory ring closure under thermal conditions.

c. A conjugated diene with an odd number of double bonds has a symmetric HOMO.

Account for the difference in the products of the following reactions:
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