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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

The reaction of cyclohexene with iodo-benzene under Heck conditions forms E, a coupling product with the new phenyl group on the allylic carbon, but none of the 鈥渆xpected鈥� coupling product F with the phenyl group bonded directly to the carbon鈥揷arbon double bond.

a. Draw a stepwise mechanism that illustrates how E is formed.

b. Step [2] in Mechanism 26.2 proceeds with syn addition of Pd and R' to the double bond.What does the formation of E suggest about the stereochemistry of the elimination reaction depicted in Step [3] of Mechanism 26.2?

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

a.

b.

c.

Draw the products formed when each alkene is treated with Grubbs catalyst.

a.

b.

c.

Devise a synthesis of each substituted cyclopropane. Use acetylene HC鈮�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.

Draw the coupling product formed when each pair of compounds is treated with Pd(OAc)2, P(o-tolyl)3, and Et3N.
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