1. Chemistry 2100 Lecture 3

2. Discovering Aromatics C6H6C6H6 1.54 Å 1.33 Å 1.39 Å

3. Aromatics

4. Resonance

13. Graphene

14. Carbon Nanotubes

15. Nomenclature for Arenes Many common names retained Blah PAH

16. Aromatic Reactions

17. Noteworthy Phenols

18. Phenol Acidity >> acids > thiols ~ phenols > water ~ alcohols Acidity: acids > phenols ~ thiols > water ~ alcohols K a % ionized [ H 3 O + ], M pH ~1  10 7 ~100 ~0.1 1.00 1.8  10 – 5 1.3 1.3  10 – 3 2.88 3.3  10 – 10 0.0036 3.6  10 – 6 5.44 2.5  10 – 11 0.0016 1.6  10 – 6 5.80 1.3  10 – 16 0.0001 1.0  10 – 7 7.00 HCl HOAc PhOH EtSH EtOH HOH Comparative acidities of 0.1 M aqueous solutions of representative acids HA 1.8  10 – 16 0.0001 1.0  10 – 7 7.00

19. Phenols as Antioxidants Autoxidation

20. Natural Phenolic Antioxidants Vitamin E  tocopherol) Resveratrol

21. Man-made Phenolic Antioxidants

22. Phenols as… Weapons?

32. "phenethylamine"

33. ephedrine (ephedra) / pseudoephedrine

35. methylenedioxymethamphetamine / MDMA / Ecstacy

39. Organic Food Dye: Carminic Acid

40. Aromatic Heterocycles nicotine niacin (B 3 ) / nicotinamide thiamine (B 1 ) caffeine (theobromine)

41. Heterocycles store life’s information (U) T = A

43.  

44.  

45.    

46.    

47.    

48. 1.085 nm (U) T = A

49. 1.085 nm (U) C = G