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History of Benzene

History of Benzene. 1824 - 1825 Isolated from burnt whale oil by Michael Faraday 1834 Eilhardt Mitscherlich finds benzene has formula of C 6 H 6. History of Benzene. 1824 - 1825 Isolated from burnt whale oil by Michael Faraday 1834 Eilhardt Mitscherlich finds benzene has formula of C 6 H 6

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History of Benzene

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  1. History of Benzene

  2. 1824 - 1825 Isolated from burnt whale oil by Michael Faraday 1834 Eilhardt Mitscherlich finds benzene has formula of C6H6 History of Benzene

  3. 1824 - 1825 Isolated from burnt whale oil by Michael Faraday 1834 Eilhardt Mitscherlich finds benzene has formula of C6H6 1861 Josef Loschmidt proposes structure for benzoic acid and aniline History of Benzene

  4. 1824 - 1825 Isolated from burnt whale oil by Michael Faraday 1834 Eilhardt Mitscherlich finds benzene has formula of C6H6 1861 Josef Loschmidt proposes structure for benzoic acid and aniline History of Benzene

  5. 1865 Friedrich August Kekulé steps into the picture History of Benzene

  6. 1865 Kekulé has a dream History of Benzene

  7. 1865 Kekule has a dream 1865 Kekule invokes sausage diagrams Bulletin de la Société Chimique de France, 3, 98 (1865) History of Benzene

  8. 1865 Kekule has a dream 1865 Kekule invokes sausage diagrams Bulletin de la Société Chimique de France, 3, 98 (1865) 1866 Kekule introduces ring model for benzene History of Benzene +

  9. 1865 Kekule has a dream 1865 Kekule invokes sausage diagrams Bulletin de la Société Chimique de France, 3, 98 (1865) 1866 Kekule introduces ring model for benzene History of Benzene +

  10. Alternate Benzene Structures

  11. Hückel’s Rules for aromaticity 1. 2 3. 4.

  12. Benzene electron distribution map

  13. Hückel’s Rules for aromaticity Aromaticity vs. antiaromaticity

  14. Hückel’s Rules for aromaticity Aromaticity vs. antiaromaticity Why 4n + 2 for aromatic and 4n for antiaromatic? Frost’s cycle

  15. Benzene Molecular Orbitals

  16. Cyclopentadienyl ions

  17. 1. methoxycyclobutadiene • Aromatic • Antiaromatic • Neither

  18. 2. tropyllium • Aromatic • Antiaromatic • Neither

  19. 3. pyrrole • Aromatic • Antiaromatic • Neither

  20. 4. imidazole • Aromatic • Antiaromatic • Neither

  21. 5. 14-annulene • Aromatic • Antiaromatic • Neither

  22. x x

  23. 6. 12-Annulene • Aromatic • Antiaromatic • Neither

  24. Inside: d – 0.5 ppm Outside: d 6.9 – 7.3 ppm

  25. CHE 311 Starts Here Section 9.6

  26. Reactivity of BenzeneElectrophilic Aromatic Substitution

  27. Reactivity of BenzeneElectrophilic Aromatic Substitution The Mechanism

  28. Reactivity of BenzeneElectrophilic Aromatic Substitution The electrophiles 1. Cl+ 2. Br+ 3. I+ 4. “F+” 5. NO2+ 6. SO3H+ 7. R+ (carbocation) 8. R-C O+

  29. Reactivity of BenzeneSubstituent Group Effects on Electrophilic Aromatic Substitution Activators and deactivators

  30. Reactivity of BenzeneSubstituent Group Effects on Electrophilic Aromatic Substitution

  31. Reactivity of BenzeneSubstituent Group Effects on Electrophilic Aromatic Substitution Directing Group Effects

  32. Activation energy vs. substituent for EAS Y, directing effect

  33. p. 340

  34. p. 345

  35. p. 338

  36. Aromatic Biomolecules • Amino acids • Nucleic acids

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