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Chapter 8: Q8-4P (page 225)

Question: Addition of HCl to 1,2-dimethylcyclohexene yields a mixture of two products. Show the stereochemistry of each, and explain why a mixture is formed.

Short Answer

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Answer

The mixture of products formed is,

Step by step solution

01

Addition of HCl to cyclohexene

The addition of HCl to cyclohexene yields a mixture of products, in which H and Cl are added to a cis or trans alkene.A carbocation intermediate is formed, then attacked by a chloride ion.

02

The mixture of products formed and its stereochemistry

The addition of HCl (hydrogen halide) to cyclohexene involves the formation of a halonium ion intermediate. A chloride ion attacks this carbocation either from the top or bottom. This reaction yields a mixture of products in which the two methyl groups can be either cis or trans to each other.

Addition of HCl to 1,2-dimethylcyclohexene

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Most popular questions from this chapter

We’ll see in the next chapter that alkynes undergo many of the same reactions that alkenes do. What product might you expect from each of the following reactions?

Question:Show the structures of alkenes that give the following products on oxidative cleavage with KMnO4 in acidic solution:

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

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