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Chapter 26: Q 28. (page 1070)

Treatment of cyclohexene with C6H5CHI2and Zn(Cu) forms two stereoisomers of molecular formula C13H16. Draw their structures and explain why two compounds are formed.

Short Answer

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01

Simmons-Smith reaction

The reaction of dihalocarbenes with the alkenes to form halogenated cyclopropanes is called the Simmons-Smith reaction.

02

Mechanism

The dihalocarbene reacts with the zinc-copper couple to form ICH2Znl, the Simmons–Smith reagent that is responsible for the transfer of the carbene (CH2)group to the alkene in a stereoselective manner to form cyclopropane.

03

Products of the given reaction

In the cyclopropane ring, only the carbon attached to the phenyl ring is stereogenic. Hence, the different orientations of the phenyl ring on this carbon give two stereoisomers, i.e., diastereomers.

The structures of the two diastereomers thus formed are shown hereunder.

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Most popular questions from this chapter

Bi-aryls, compounds containing two aromatic rings joined by a C-C bond, can often be efficiently made by two different Suzuki couplings; that is, either aromatic ring can be used to form the organoborane needed for coupling. In some cases, however, only one route is possible. With this in mind, synthesize each of the following bi-aryls using benzene as the starting material for each aromatic ring. When more than one route is possible, draw both of them. You may use any required organic or inorganic reagents.

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

a.

b.

c.

Metathesis reactions can be carried out with two different alkene substrates in one reaction mixture. Depending on the substitution pattern around the C=C, the reaction may lead to one major product or a mixture of many products. For each pair of alkene substrates, draw all metathesis products formed. (Disregard any starting materials that may also be present at equilibrium.) With reference to the three examples, discuss when alkene metathesis with two different alkenes is a synthetically useful reaction.

One step in the synthesis of the nonsteroidal anti-inflammatory drug rofecoxib (trade name Vioxx) involves Suzuki coupling of A and B. What product is formed in this reaction?

What products are formed when cis-pent-2-ene undergoes metathesis? Use this reaction to explain why metathesis of a 1, 2-disubstituted alkene (RCH=CHR') is generally not a practical method for alkene synthesis?
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