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Chapter 26: Q 36 (page 1071)

Draw a stepwise mechanism for the following reaction.

Short Answer

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Answer

Mechanism

Step by step solution

01

Substrates of the Simmons-Smith reaction

The substrates of the Simmons-Smith reaction include a dihalocarbene and an alkene.

02

Mechanism of the Simmons-Smith reaction

The dihalocarbene reacts with the zinc-copper couple to form the Simmons-Smith reagent, i.e., XCH2ZnX, which transfers the CH2 group to the alkene. Both C=C carbons join the CH2 group to form a cyclopropane.

03

Mechanism of the given reaction

The Zn-Cu couple reacts with the carbon-containing two bromide groups and forms on the dihalo center of the ring. The Simmons-Smith reagent thus attacks the double bond in the ring to form a cyclopropane ring.

The mechanism of the given reaction is shown below.

Mechanism

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Most popular questions from this chapter

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?

Sulfur ylides, like the phosphorus ylides of Chapter 21, are useful intermediates in organic synthesis. Methyl trans-chrysanthemate, an intermediate in the synthesis of the insecticide pyrethrin I (Section 26.4), can be prepared from diene A and a sulfur ylide. Draw a stepwise mechanism for this reaction.

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

a.

b.

c.

Many variations of ring-closing metathesis have now been reported. Tandem ring-opening– ring-closing metathesis can occur with cyclic alkenes that contain two additional carbon– carbon double bonds. In this reaction, the cycloalkene is cleaved, and two new rings are formed. [1] What compounds are formed in this tandem reaction with the following substrates? [2] Devise a synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethyl maleate as the dienophile.

a.

b.

Although diazomethane ( CH2N2) is often not a useful reagent for preparing cyclopropanes,other diazo compounds give good yields of more complex cyclopropanes. Draw a stepwisemechanism for the conversion of diazo compound A to B, an intermediate in the synthesis ofsirenin, the sperm attractant produced by the female gametes of the water mold Allomyces.
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