Although most alkanes react with chlorine by a radical chain mechanism when reaction

Chapter 21, Problem 21.44

(choose chapter or problem)

Although most alkanes react with chlorine by a radical chain mechanism when reaction isinitiated by light or heat, benzene fails to react under the same conditions. Benzene cannotbe converted to chlorobenzene by treatment with chlorine in the presence of light or heat. (a) Explain why benzene fails to react under these conditions. (Consult Appendix 3 forrelevant bond dissociation enthalpies.)(b) Explain why the bond dissociation enthalpy of a C!H bond in benzene is signifi-cantly greater than that in alkanes.

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