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Chapter 8: Q8-3P. (page 225)

Question: What product would you expect to obtain from addition of to 1,2-dimethyl-cyclohexene? Show the stereochemistry of the product.

Short Answer

Expert verified

Answer

The product obtained is,

Step by step solution

01

Halogenation of alkene

In the halogenation of alkene, bromine and chlorine adds rapidly and give 1,2-dihalides.When halogenations occur in cycloalkene, only trans stereoisomers are formed by dihalide addition.

02

The product obtained from the addition of Cl2to 1, 2-dimethyl-cyclohexene

The addition ofCl2to a cycloalkene takes place by the electrophilic addition of Cl+to the alkene, forming a carbocation intermediate. On further reaction with Cl-, dichloride addition product is obtained. The chlorines are tans to one another like methyl groups.

Formation of product from the addition of Cl2to 1,2-dimethyl-cyclohexene

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Most popular questions from this chapter

Show the structures of alkenes that give the following products on oxidative cleavage with in acidic solution.

Compound A, C10H18O, undergoes reaction with dilute H2SO4at 50 掳C to yield a mixture of two alkenes, C10H16. The major alkene product, B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Identify A and B, and write the reactions.

Cyclopentanone

Draw the structure of a hydrocarbon that absorbs 2 molar equivalents of H2 on catalytic hydrogenation and gives only butanedial on ozonolysis.

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Question:How would you carry out the following transformations? Tell what

reagents you would use in each case.

The reaction of cyclohexene with mercury(II) acetate in CH3OH rather than

H2O, followed by treatment with NaBH4, yields cyclohexyl methyl ether rather than cyclohexanol. Suggest a mechanism.
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