Ch_322b_15.04 - Chapter 15.4 lecture note

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Friedel-Crafts Alkylation This reaction was discovered in 1877 by Charles Friedel, a French chemist, and his American collaborator, James Crafts. This alkylation reaction (introduction of an alkyl group), and the related acylation reaction (introduction of an acyl group), are among the most useful synthetic reactions in organic chemistry. Alkylation: Introduction of an Alkyl Group into an Arene + R -X AlCl 3 R + HX alkyl halide alkylbenzene The reaction of benzene with an alkyl halide requires a Lewis acid catalyst , typically aluminum chloride, AlCl 3 . Many variations of the original Friedel-Crafts alkylation reaction have been developed in the past 100 years. They all proceed by similar mechanisms.
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A Mechanism for the Alkylation Reaction The Lewis acid catalysts that are often required in the Friedel-Crafts reactions promote formation of strong electrophiles . (1) Generation of the Electrophile R-Cl: : : + AlCl 3 Lewis acid R-Cl-AlCl 3 : : - + complex Lewis base With 2 o and 3 o R-Cl compounds, dissociation to carbocation
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