Chemistry of Aromatic Compounds - PowerPoint PPT Presentation

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Chemistry of Aromatic Compounds
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Chemistry of Aromatic Compounds

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  1. Chemistry of Aromatic Compounds Electrophilic Aromatic Substitution Directing Effects Side-chain Reactions Synthesis Nucleophilic Aromatic Substitution

  2. Electrophilic Aromatic Substitution

  3. EAS Reactions of Benzene

  4. Bromination / Chlorination

  5. Bromination Mechanism

  6. Reaction Profile

  7. Nitration

  8. Nitration Mechanism

  9. Nitration of Toluene

  10. Sulfonation is Reversible

  11. Desulfonation

  12. Friedel-Crafts Acylation

  13. 1st, Formaton of Electrophile

  14. Acylation Mechanism

  15. Intermediate is Resonance-Stabilized

  16. An Acylation

  17. Friedel-Crafts Alkylationmany more limitations

  18. Mechanism

  19. Carbocation Generated From Alkene

  20. Unexpected Product?

  21. Carbocations Rearrange…

  22. 1o RX Typically Undergoes Shift

  23. Side Chain Reactions 1) Reduction of Aromatic Ketones

  24. Straight-chain Alkylation can be Accomplished in 2 steps:Acylation, then Reduction

  25. 2) Oxidation of Alkyl Substituents

  26. 3) Benzylic Bromination with NBS

  27. 4) Alkali Fusion of Sulfonic Acids

  28. 5) Reduction of Nitro Groups

  29. Directing Effects

  30. ortho/para-Directing Activating Groups

  31. Nitration of Anisole

  32. Nitration Affords ortho and paraProducts

  33. Activating ortho/para directors

  34. Nitration of Toluene

  35. meta-Directing Deactivating Groups

  36. Electron-Withdrawing Nitro Group Directs meta

  37. meta Directors

  38. Comparison

  39. More Limitations with Friedel Crafts Reactions

  40. Substituent Summary

  41. Halogens are the AnomolyDeactivators and o,p-Directors

  42. Reactions of Rings With Two or More Substituents

  43. The (More) Activated Ring Reacts

  44. Mixtures with Conflicting Directing Effects

  45. Provide the Reagents

  46. Must Acylate First

  47. Sulfonic Acid Blocks para Position