1. University Of Pennsylvania College of General Studies Professor William A. Price, Ph.D. CHEM 241-601 Organic Chemistry, 9 th Edition By T.W. Graham Solomons

2. From the Bark of the Pacific Yew Tree

3. Introduction: Structure and Bonding Atomic structure Lewis Structures Resonance Structural Formulas Acids and Bases

4. Nucleus is a Tiny Fraction of the Volume of an Atom

5. Orbitals are Probabilities

6. 2s Orbital Has a Node

7. The p Orbital

8. p x, p y, p z

9. Electron Configurations

10. Lewis Dot Structure of Methane

11. Tetrahderal Geometry

13. Bonding Characteristics of Period 2 Elements

14. “Saturated” with Hydrogen

15. All Have the Same Geometry All Have 4 Regions of Electron Density

16. A Saturated Hydrocarbon

17. Nitromethane

18. Nitromethane has 2 Formal Charges

19. Both Resonance Structures Contribute to the Actual Structure

20. Resonance Rules Cannot break single (sigma) bonds Only electrons move, not atoms 3 possibilities: –Lone pair of e - to adjacent bond position Forms  bond  bond to adjacent atom  bond to adjacent bond position

21. Curved Arrow Formalism Shows flow of electrons

22. Resonance Stabilization of Ions Pos. charge is “delocalized”

23. Bonding Pattens for C, N, and O

24. Common Cationic, Neutral and Anionic Forms

25. Two Nonequivalent Resonance Structures in Formaldehyde

26. Resonance in Acetate Anion

27. Resonance in [CH 2 NH 2 ] +

28. Propose Lewis Structures a)H 2 CO 2 b) O 3 c) N 2 O d) NH 3 Oe) C 2 H 3 ClO f) C 2 H 5 NO

29. Problem Draw [NO 2 ] + and [NO 2 ] -. Which ion has a “localized” charge and which has a “delocalized” charge. Explain.

30. Drawing Structures

31. Octane Representations

32. Condensed Formulas

33. Line-Angle Structures are Often Used as a Short-hand

34. Line-Angle Structures

36. Line-Angle structure Superimposed on Lewis Structure

37. Double Bonds are Shown

38. For Cyclic Structures, Draw the Corresponding Polygon

39. Some Steroids

40. Adrogenic/Anabolic Steroids

41. Anabolic Steroids

42. Benzene can be drawn as one of two resonance structures

43. Some Line-Angle Structures