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Chapter 26: Q 29. (page 1070)

What ring-closing metathesis product is formed when each substrate is treated with Grubbs catalyst under high-dilution conditions?

a.

b.

c.

Short Answer

Expert verified

Answer

Product of b

Step by step solution

01

Ring-closing metathesis

Under the reactions of olefinic metathesis, the intramolecular metathesis of the terminal alkenes that form multiple unsaturated rings is called ring-forming metathesis. The cycloalkenes formed are E and Z isomers.

02

Grubbs catalyst

The series of the transition metal carbenes used especially for olefinic metathesis are the Grubbs catalysts.

03

Products of the given reaction

Under high-dilution conditions, the Grubbs catalyst favors the intramolecular ring-closing metathesis.

a. A six-membered ring is formed by the intramolecular metathesis. The product is shown below.


Product of a

b. A six-membered ring is formed by the intramolecular metathesis. The product is shown below.

Product of b

c. A five-membered ring is formed by the intramolecular metathesis. The product is shown below.

Product of c

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Most popular questions from this chapter

How can you convert ethynylcyclohexane to dienes A–C using a Suzuki reaction? You may use any other organic compounds and inorganic reagents. Is it possible to synthesize diene D using a Suzuki reaction? Explain why or why not.

Devise a synthesis of diene A from (Z)-2-bromostyrene as the only organic starting material. Use a Suzuki reaction in one step of the synthesis.

Draw the products formed in each reaction.

a.

b.

c.

d.

e.

f.

g.

h.

Devise a synthesis of each substituted cyclopropane. Use acetylene HC≡CH, as a startingmaterial in part (a), and cyclohexanone as a starting material in part (b). You may use anyother organic compounds and any needed reagents.

a.

b.

What product is formed by ring-closing metathesis of compound V, a key intermediate in the synthesis of ingenol, a natural product mentioned in the chapter opener?
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