Reactions of Aromatic Compounds

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(2) Electrophilic Attack + or + R-Cl-AlCl 3 : : - + R + AlCl 4 - H R + (3) Deprotonation and Re-aromatization H R + :Cl: + :Cl - Al : : : : :Cl : Lewis base Cl: : : Arenium ion R Alkylbenzene etc. + AlCl 4 - + HCl + AlCl 3 Regenerated catalyst
Evidence for Carbocation Intermediates Skeletal rearrangement is observed in Friedel-Crafts alkylation reactions when concurrent change to a more stable carbocation can occur. + CH 3CH 2CH 2Br AlCl 3 CH3 CH CH3 Propyl bromide Isopropylbenzene It is believed rearrangement occurs during reversible dissociation to a short-lived carbocation: + - CH3CH2CH2-Br-AlCl3 Complex 1 + CH3CH2CH2 + CH3CHCH3 + HBr + AlBrCl 4 + - (CH3) 2CH-Cl-AlBrCl2 Complex 2
Page 1 and 2: Chapter 15 Reactions of Aromatic Co
Page 3 and 4: Examples of Electrophilic Aromatic
Page 5 and 6: Step 2: Deprotonation of the Areniu
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: A Mechanism for the Alkylation Reac
Page 23: 2) Alcohols alkylate arenes in the

Reactions of Aromatic Compounds

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