Chapter12

Chapter12 - Organic Chemistry CHE 275 Chapter 12 Reactions...

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Organic Chemistry CHE 275 Chapter 12 Reactions of Arenes: Aromatic Substitution
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Electrophilic Aromatic Substitution
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Representative Electrophilic Aromatic Substitution Reactions of Benzene
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Nitration of Benzene
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Sulfonation of Benzene
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Friedel-Crafts Alkylation of Benzene
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Friedel-Crafts Acylation of Benzene
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Mechanistic Principles of Electrophilic Aromatic Substitution
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Step 1: attack of electrophile on ! -electron system
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Step 2: Loss of a Proton from the Carbocation Intermediate
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H H H H H + E + H E H H H H + H + H H H H H H H E +
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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
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Step 1: Attack of the ! -Electron System on the Nitronium Cation
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Step 2: Loss of a Proton
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Sulfonation of Benzene
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Step 1: attack of the ! -electron system on sulfur trioxide
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Step 3: Protonation of the Benzenesulfonate Ion
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Halogenation of Benzene
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The Br 2 -FeBr 3 Complex
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Step 1: Attack of the ! -Electron System on the tert-Butyl Cation
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This note was uploaded on 10/17/2011 for the course CHE 275 taught by Professor Totah during the Fall '08 term at Syracuse.

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Chapter12 - Organic Chemistry CHE 275 Chapter 12 Reactions...

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