ch15 - Chapter15 Reactionsof AromaticCompounds...

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Click to edit Master subtitle  style Created by Professor William Tam & Dr. Phillis Chang 1Ch. 15 - 1 Chapter 15 Reactions of Aromatic Compounds
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2Ch. 15- 2 About The Authors These PowerPoint Lecture Slides were created and prepared by Professor  William Tam and his wife, Dr. Phillis Chang.   Professor William Tam received his B.Sc. at the University of Hong Kong in  1990 and his Ph.D. at the University of Toronto (Canada) in 1995.  He was an  NSERC postdoctoral fellow at the Imperial College (UK) and at Harvard University  (USA).  He joined the Department of Chemistry at the University of Guelph  (Ontario, Canada) in 1998 and is currently a Full Professor and Associate Chair in  the department.  Professor Tam has received several awards in research and  teaching, and according to  Essential Science Indicators , he is currently ranked as  the Top 1% most cited Chemists worldwide.  He has published four books and over  80 scientific papers in top international journals such as  J. Am. Chem. Soc., Angew.  Chem., Org. Lett.,  and  J. Org. Chem.   Dr. Phillis Chang received her B.Sc. at New York University (USA) in 1994, her 
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3Ch. 15 - 3 1. Electrophilic Aromatic Substitution Reactions v Overall reaction H E H + E + +
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4Ch. 15 - 4 X X 2 Fe X 3 NO 2 H NO 3 H 2 SO 4 R R Cl AlCl 3 R O R Cl O AlCl 3 SO 3 H H 2 SO 4 SO 3
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5Ch. 15 - 5 2. A General Mechanism for Electro- philic Aromatic Substitution v Different chemistry with alkene C C Br 2 Br C C Br Br 2 + + No Reaction
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6Ch. 15 - 6 v Benzene does not undergo  electrophilic   addition , but it undergoes  electrophilic   aromatic  substitution + H E A H A E ( H  substituted by  E )
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7Ch. 15 - 7 v Mechanism Step 1 E + E slow r.d.s. E E
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8Ch. 15 - 8 E H B v Mechanism Step 2 E B H + fast
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9Ch. 15 - 9
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10Ch. 15 - 10 3. Halogenation of Benzene v Benzene does not react with Br2 or Cl2 unless a Lewis acid is present  (catalytic amount is usually enough)
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11Ch. 15 - 11 v Examples Cl HCl Cl 2 + FeCl 3 25 o (90%) Br HBr Br 2 + 3 heat (75%) Reactivity: F2 > Cl2 > Br2 > I2
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12Ch. 15 - 12 v Mechanism Br Br FeBr 3 (weak electrophile) δ - δ + Br Br FeBr 3 Br    +  FeBr 4 (very reactive electrophile)
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13Ch. 15 - 13 Br Br Br Br slow r.d.s. v Mechanism (Cont’d)
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14Ch. 15 - 14 v Mechanism (Cont’d) Br H Br FeBr 3 Br Br H + +  FeBr 3
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15Ch. 15 - 15 v F2 : too reactive, give mixture of mono-, di- and highly substituted products  F F F F F + + + others F 2 Lewis acid
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16Ch. 15 - 16 v I2 : very unreactive even in the presence of Lewis acid, usually need to add an  oxidizing agent (e.g. HNO3, Cu2+, H2O2) I I 2 HNO 3 (86%) e.g.
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ch15 - Chapter15 Reactionsof AromaticCompounds...

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