惯-Chapter 12Reactions of ArenesElectrophilic Aromatic Substitut.ppt

惯-Chapter 12Reactions of ArenesElectrophilic Aromatic Substitut.ppt

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惯-Chapter 12Reactions of ArenesElectrophilic Aromatic Substitut

Chapter 12 Reactions of Arenes: Electrophilic Aromatic Substitution 12.1 Representative Electrophilic Aromatic Substitution Reactions of Benzene Electrophilic aromatic substitutions include: Nitration Sulfonation Halogenation Friedel-Crafts Alkylation Friedel-Crafts Acylation Table 12.1: Nitration of Benzene Table 12.1: Sulfonation of Benzene Table 12.1: Halogenation of Benzene Table 12.1: Friedel-Crafts Alkylation of Benzene Table 12.1: Friedel-Crafts Acylation of Benzene 12.2 Mechanistic Principles of Electrophilic Aromatic Substitution Step 1: attack of electrophile on p-electron system of aromatic ring highly endothermic carbocation is allylic, but not aromatic Step 2: loss of a proton from the carbocation intermediate highly exothermic this step restores aromaticity of ring Based on this general mechanism: what remains is to identify the electrophile in nitration, sulfonation, halogenation, Friedel-Crafts alkylation, and Friedel-Crafts acylation to establish the mechanism of specific electrophilic aromatic substitutions 12.3 Nitration of Benzene Nitration of Benzene Step 1: attack of nitronium cation on p-electron system of aromatic ring Step 2: loss of a proton from the carbocation intermediate Where does nitronium ion come from? 12.4 Sulfonation of Benzene Sulfonation of Benzene Step 1: attack of sulfur trioxide on p-electron system of aromatic ring Step 2: loss of a proton from the carbocation intermediate Step 3: protonation of benzenesulfonate ion 12.5 Halogenation of Benzene Halogenation of Benzene The Br2-FeBr3 Complex The Br2-FeBr3 complex is more electrophilic than Br2 alone. Step 1: attack of Br2-FeBr3 complex on p-electron system of aromatic ring Step 2: loss of a proton from the carbocation intermediate 12.6 Friedel-Crafts Alkylation of Benzene Friedel-Crafts Alkylation of Benzene Role of AlCl3 acts as a Lewis acid to promote ionization of the alkyl halide Role of AlCl3 acts as a Lewis acid to promote ionization of the

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