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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

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.

Problem:a. For conjugated systems with two, three, four, five, six, and seven conjugated蟺 bonds, construct quick MOs (just draw the lobes at the ends of the conjugated system as they are drawn on pages 1220 and 1221) to show whether the HOMO is symmetric or antisymmetric.

b. Using these drawings, convince yourself that the Woodward鈥揌offmann rules in Table 28.1 are valid.

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

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?

Explain why two different products are formed from disrotatory ring closure of (2E,4Z,6Z)-octatriene, but only one product is formed from disrotatory ring closure of (2E,4Z,6E)-octatriene.
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