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Mastering Electrophilic Aromatic Substitution in Chemistry

Dive into the world of aromatic compounds with a focus on EAS reactions, directing effects, side-chain reactions, and synthesis. Learn about important mechanisms like nitration and sulfonation, as well as the impacts of activating and deactivating groups. Understand the complexities of Friedel-Crafts reactions and the rearrangement of carbocations in alkylation processes.

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Mastering Electrophilic Aromatic Substitution in Chemistry

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  1. Name the following compounds

  2. Draw the following compounds p-isopropylbenzoic acid 2-bromo-4-nitrotoluene m-methoxybenzonitrile

  3. Which of the following are aromatic compounds?

  4. Draw resonance forms for each of the following.

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

  6. Electrophilic Aromatic Substitution

  7. EAS Reactions of Benzene

  8. Bromination / Chlorination

  9. Bromination Mechanism

  10. Reaction Profile

  11. Nitration

  12. Nitration Mechanism

  13. Nitration of Toluene

  14. Sulfonation is Reversible

  15. Desulfonation

  16. Friedel-Crafts Acylation

  17. 1st, Formaton of Electrophile

  18. Acylation Mechanism

  19. Intermediate is Resonance-Stabilized

  20. An Acylation

  21. Friedel-Crafts Alkylation

  22. Mechanism

  23. Carbocation Generated From Alkene

  24. Unexpected Product?

  25. Carbocations Rearrange…

  26. 1o RX Typically Undergoes Shift

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

  28. Side Chain Reactions 1) Reduction of Aromatic Ketones

  29. 2) Oxidation of Alkyl Substituents

  30. 3) Benzylic Bromination with NBS

  31. 4) Alkali Fusion of Sulfonic Acids

  32. 5) Reduction of Nitro Groups

  33. Directing Effects

  34. ortho/para-Directing Activating Groups

  35. Nitration of Anisole

  36. Nitration Affords ortho and paraProducts

  37. Activating ortho/para directors

  38. Nitration of Toluene

  39. meta-Directing Deactivating Groups

  40. Electron-Withdrawing Nitro Group Directs meta

  41. meta Directors

  42. Comparison

  43. More Limitations with Friedel Crafts Reactions

  44. Substituent Summary + due to resonance o/p due to resonance ─ due to inductive effect o/p due to resonance + due to inductive effect o/p due to inductive effect ─ due to resonance and inductive effect meta due to inductive effect

  45. Halogens are the AnomalyDeactivators and o,p-Directors

  46. Reactions of Rings With Two or More Substituents

  47. The (More) Activated Ring Reacts

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