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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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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

What steps are needed to convert but-1-ene \((C{H_3}C{H_2}CH = C{H_2})\) to octane \((C{H_3}{(C{H_2})_6}C{H_3})\)using a coupling reaction with an organocuprate reagent? All carbon atoms in octane mustcome from but-1-ene.

Devise a synthesis of each compound from cyclohexene and any required organic or inorganic reagents.

a.

b.

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 “expected” coupling product F with the phenyl group bonded directly to the carbon–carbon 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?

Draw the product formed from ring-closing metathesis of each compound.

a.

b.

What product is formed by ring-closing metathesis of each compound?

a.

b.
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