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Ch 22 notes - Chemistry 140C Spring 2009(K Albizati Chapter...

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Chemistry 140C Spring 2009 (K. Albizati) 1 Chapter 22 – Chemistry of Benzene Substituents The benzene ring makes the C-H bonds in the benzylic positions much more reactive in a variety of transformations: For example: Bromination under free radical conditions gives rise to benzylic bromination and not ring bromination. Recall the propagation steps in radical halogenation reactions: Recall also that the more stable radicals form faster than less stabilized radicals. The benzylic radical is resonance stabilized:
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