Although most alkanes react with chlorine by a radical chain mechanism when reaction is initiated by light or heat, benzene fails to react under the same conditions. Benzene cannot be converted to chlorobenzene by treatment with chlorine in the presence of light or heat. light -H + Clg -Cl + HCI or heat

General, Organic, and Biological Chemistry
7th Edition
ISBN:9781285853918
Author:H. Stephen Stoker
Publisher:H. Stephen Stoker
Chapter13: Unsaturated Hydrocarbons
Section: Chapter Questions
Problem 13.119EP
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Explain why the bond dissociation enthalpy of a C-H bond in benzene is significantly greater than that in alkanes

Although most alkanes react with chlorine by a radical chain mechanism when reaction is
initiated by light or heat, benzene fails to react under the same conditions. Benzene cannot
be converted to chlorobenzene by treatment with chlorine in the presence of light or heat.
light
-H + Clg
-Cl + HCI
or heat
Transcribed Image Text:Although most alkanes react with chlorine by a radical chain mechanism when reaction is initiated by light or heat, benzene fails to react under the same conditions. Benzene cannot be converted to chlorobenzene by treatment with chlorine in the presence of light or heat. light -H + Clg -Cl + HCI or heat
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