Reactions of Aromatic Compounds

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Description of Mechanism Using Resonance Structures Step 1: Attack by the Electrophile Two π-electrons form a σ-bond to the incoming electrophile yielding a delocalized carbocation intermediate called an arenium ion. δ E A + δ - - A: H E + + H E + - These resonance structures show the distribution of positive charge in the arenium ion. The arenium ion is non-aromatic, but it is reasonably stable because of charge dispersal over the carbons ortho and para to the site of attachment of the electrophile. δ+ H E δ+ δ+ H E
Step 2: Deprotonation of the Arenium Ion and Re-aromatization H E + + A: - E + H-A The Lewis base that attacks and removes the proton may, as shown, be the conjugate base of the electrophile or some other Lewis base that may be present.
Page 1 and 2: Chapter 15 Reactions of Aromatic Co
Page 3: Examples of Electrophilic Aromatic
Page 7 and 8: Halogenation of Benzene Halogenatio
Page 9 and 10: Mechanism: Step 1: Electrophilic At
Page 11 and 12: Iodination of Benzene Direct iodina
Page 13 and 14: Mechanism of Nitration (1) Generati
Page 15 and 16: Sulfonation of Benzene Benzene reac
Page 17 and 18: (4) Acid-Base Equilibrium :O: S O:
Page 19 and 20: A Mechanism for the Alkylation Reac
Page 21 and 22: Evidence for Carbocation Intermedia
Page 23: 2) Alcohols alkylate arenes in the

Reactions of Aromatic Compounds

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