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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

Synthesize each compound from the given starting materials.

Draw the product formed from the ring-closing metathesis of each compound. Then, devisea synthesis of each metathesis starting material using any of the following compounds: CH2(CO2Et)2, alcohols with less than five carbons, and any needed organic and inorganicreagents.

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.

Devise a synthesis of each compound using a Heck reaction as one step. You may use benzene, CH2=CHCO2Et, organic alcohols having two carbons or fewer and any required inorganic reagents.

a.

b.

What starting material is needed to synthesize each compound by a ring-closing metathesis reaction?

a.

b.

c.
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