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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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a.

b.
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