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Free-radical chlorination of hexane gives very poor yields of 1-chlorohexane

Chapter 4, Problem PROBLEM 4-4

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QUESTION:

Free-radical chlorination of hexane gives very poor yields of 1-chlorohexane, whilecyclohexane can be converted to chlorocyclohexane in good yield.(a) How do you account for this difference?(b) What ratio of reactants (cyclohexane and chlorine) would you use for the synthesis ofchlorocyclohexane?

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QUESTION:

Free-radical chlorination of hexane gives very poor yields of 1-chlorohexane, whilecyclohexane can be converted to chlorocyclohexane in good yield.(a) How do you account for this difference?(b) What ratio of reactants (cyclohexane and chlorine) would you use for the synthesis ofchlorocyclohexane?

ANSWER:

Problem 4-4

Free-radical chlorination of hexane gives very poor yields of 1-chlorohexane, while cyclohexane can be converted to chlorocyclohexane in good yield. (a) How do you account for this difference? (b) What ratio of reactants (cyclohexane and chlorine) would you use for the synthesis of chlorocyclohexane?

                                                              Step by step solution

Step 1 of 3

(a)

Hexane has three different kinds of hydrogens. They are shown as follows.

But cyclohexane has only one type of carbon atom.

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