1. Alkenes Addition Reactions Synthesis

4. Addition of HBr or HCl Markovnikov Addition

5. HBr Addition with RO-OR Anti-Markovnikov

6. Free-Radical Mechanism

7. Addition of Br 2

8. A Similar Mechanism to the Addition of HBr?

9. Trans is formed exclusively ( No cis is formed)

10. Carbocation can be Stabilized by Neighboring Br

12. Bromonium Ion is Opened Equally from Both Sides

13. Definitions Stereospecific – only one stereoisomer is formed at the expense of the other (e.g. trans vs. cis) Stereoselective – one stereoisomer is formed preferentially over the other.

14. Anti-Addition Stereospecific Reaction Anti-addition

15. Bromonium Ion Intermediate

16. Halohydrins

17. Bromohydrin Formation Addition of Br – OH Stereospecific & Regiospecific

18. Unsymmetrical Bromonium ion H 2 O opens ring at more hindered site

20. Br and OH are trans in anti addition

21. Catalytic Hydrogenation syn addition

23. Mechanism – Syn Addition

24. Syn Addition of H 2

25. Hydrogenation all alkene  bonds are reduced

27. Hydrogenated Vegetable Oil

29. Hydration Addition of H 2 O

30. Oxymercuration Hydration Markovnikov addition Regiospecific Reaction

31. Oxymercuration Mechanism

33. Predict the Oxymercuration Hydration Products

34. What Alkene would you use to Make These Alcohols?

35. Hydroboration Hydration Anti-Markovnikov Syn addition

36. BH 3 adds to Alkene

37. Hydroboration

38. Regiochemistry is Anti-Markovnikov

40. Syn Addition of H 2 O

41. Draw the Major Products

42. 2 Complementary Hydration Reactions

43. Oxymercuration – the more highly substituted alcohol forms Hydroboration – the less highly substituted alcohol forms

44. Predict Both Oxymercuration and Hydroboration Products

45. Cyclopropanation

47. A Carbene is Similar to Geometry of a Carbocation

48. Dichlorocarbene Reactions

49. Simmons-Smith Reaction

50. In situ Preparation of Carbene

53. Two MCAD Inhibitors

54. Epoxide Preparation From Alkenes

55. Epoxide Preparation From Halohydrins

56. Mechanism

57. Epoxide groups are Common in Biologically Active Molecules

58. A New Class of Anti-tumor Agents

59. Ozonolysis Forms 2 Carbonyl Compounds

60. Ozonolysis Alkene Cleavage

61. Mechanism of Ozonolysis

63. What Alkene will Undergo Ozonolysis to Give the Products Shown?

65. Addition polymers

66. Air Pollution Reacts with Tires

67. O 3 reacts with all alkene  Bonds

68. Problem A symmetrical unknown compound A, C 8 H 16, reacts with H 2 on a 1% Pt/C catalyst to form B (C 8 H 18 ). Treatment of A with O 3 followed by Zn/HOAc affords butanone only. Identify A and B.