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?

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?

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter6: An Overview Of Organic Reactions

Section6.3: Radical Reactions

Problem 2P

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Question

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?

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