1. Addition Reactions Synthesis
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 Br2

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. Bromonium Ion Intermediate

15. Halohydrins

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

17. Unsymmetrical Bromonium ion H2O opens ring at more hindered site

18. Br and OH are trans in anti addition

19. Catalytic Hydrogenation syn addition

21. Mechanism – Syn Addition

22. Syn Addition of H2

23. Hydrogenation all alkene p bonds are reduced

25. Hydrogenated Vegetable Oil

27. Hydration Addition of H2O

28. Oxymercuration Hydration Markovnikov addition Regiospecific Reaction

29. Oxymercuration Mechanism

31. Predict the Oxymercuration Hydration Products

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

33. Hydroboration Hydration Anti-Markovnikov Syn addition

34. BH3 adds to Alkene

35. Hydroboration

36. Regiochemistry is Anti-Markovnikov

38. Syn Addition of H2O

39. Draw the Major Products

40. 2 Complementary Hydration Reactions

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

42. Predict Both Oxymercuration and Hydroboration Products

43. Epoxide Preparation From Halohydrins

44. Mechanism

45. Epoxide groups are Common in Biologically Active Molecules

46. A New Class of Anti-tumor Agents

47. Ozonolysis Forms 2 Carbonyl Compounds

48. Ozonolysis Alkene Cleavage

49. Mechanism of Ozonolysis

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

53. Problem
A symmetrical unknown compound A, C8H16, reacts with H2 on a 1% Pt/C catalyst to form B (C8H18). Treatment of A with O3 followed by Zn/HOAc affords butanone only. Identify A and B.