Ch_322b_15.13 - Chapter 15.13 lecture note

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Reactions of the Side Chain of Alkyl Benzenes Hydrocarbons containing both aromatic and aliphatic groups are also called arenes . Some examples are shown below. CH 3 CH 2 CH 2 CH 3 toluene propylbenzene alkylbenzenes CH=CH 2 phenylethene (styrene or vinylbenzene) an alkenylbenzene Alkylbenzenes and alkenylbenzenes have characteristic reactivities because of the presence of the aromatic ring.
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Functionalization of the Side Chain of Alkylbenzenes: Benzylic Radicals and Cations. Removal of an hydrogen atom (H ) from an ! -carbon of an alkylbenzene produces a benzyl radical . . CH 2 CH 2 CH 2 ! " # -H . CHCH 2 CH 2 . a benzyl-type radical The Stability of Benzyl-type Radicals Benzyl-type radicals are more stable than simple alkyl radicals because they are delocalized through interaction with the aromatic ! -system. This interaction may be described by resonance structures, or by an orbital structural formula, as shown below. C .
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