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

14. 1st, Formaton of Electrophile

15. Acylation Mechanism

16. Intermediate is Resonance-Stabilized

17. An Acylation

18. Friedel-Crafts Alkylation

20. Mechanism

21. Unexpected Product?

22. Carbocations Rearrange…

23. 1o RX Typically Undergoes Shift

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

25. Side Chain Reactions
1) Reduction of Aromatic Ketones

26. 2) Oxidation of Alkyl Substituents

27. 3) Benzylic Bromination with NBS

28. 5) Reduction of Nitro Groups

29. Directing Effects

30. ortho/para-Directing Activating Groups

31. Nitration of Anisole

32. Nitration Affords ortho and para Products

33. Activating ortho/para directors

34. Nitration of Toluene

35. meta-Directing Deactivating Groups

36. Electron-Withdrawing Nitro Group Directs meta

38. meta Directors

39. Comparison

40. More Limitations with Friedel Crafts Reactions

41. Substituent Summary

42. Halogens are the Anomaly Deactivators and o,p-Directors

43. Reactions of Rings With Two or More Substituents

44. The (More) Activated Ring Reacts

45. Mixtures with Conflicting Directing Effects

46. Provide the Reagents

47. Must Acylate First

48. Sulfonic Acid Blocks para Position

49. Problem Set: Give the Reagents

50. Provide the Reagents