ALDEHYDES AND KETONES I. Nucleophilic Addition to Carbonyl

1. ALDEHYDES AND KETONESI.Nucleophilic Addition to Carbonyl Chapter 16 WWU Chemistry

2. Reading Assignment • SKIP: Section 16.8 • SKIP: Section 16.19 • I will be covering the remaining sections. WWU Chemistry

3. Problem Assignment • In-Text Problems 16.1 and 2 3 (except for d) 5 - 10 12 - 18 21 - 25 • End-of-Chapter 1 3 - 5 7 (all but b) 8 b, c, d 10 12 WWU Chemistry

4. Nomenclature of ketones 2,5-dimethyl-3-hexanone WWU Chemistry

5. 2,5-dimethyl-5-hexen-3-one WWU Chemistry

6. 2,6-dimethyl-1,4-cyclohexanedione WWU Chemistry

7. 5,6-dimethyl-5,7-octadien-3-one WWU Chemistry

8. 5-bromo-2-methylacetophenone WWU Chemistry

9. Some Common Names of ketones WWU Chemistry

10. Nomenclature of aldehydes 3,4-dimethylpentanal WWU Chemistry

11. 3,4-dimethyl-3,5-hexadienal WWU Chemistry

12. 4,5-dimethyl-2,4-heptadienedial WWU Chemistry

13. 3,4-dibromobenzaldehyde WWU Chemistry

14. Some common names of aldehydes WWU Chemistry

15. Sect. 16.5: Nucleophilic Addition to Carbonyl -- in base WWU Chemistry

16. Nucleophilic Addition to Carbonyl -- in Acid WWU Chemistry

17. Sect. 16.6: Addition of Cyanide WWU Chemistry

18. Sect. 16.7: Addition of Organometallic Reagents WWU Chemistry

19. Synthesis of Alcohols using Grignard reagents- revisited ketone tertiary alcohol WWU Chemistry

20. Synthesis of Alcohols Reaction of RMgBr with aldehydes and ketones yields alcohols formaldehyde primary alcohol RMgX + other aldehydes secondary alcohol RMgX + RMgX + ketones tertiary alcohol The type of alcohol depends on whether you use formaledhyde, another aldehyde, or a ketone. WWU Chemistry

21. Sect. 16.9: Addition of Water WWU Chemistry

22. Sect. 16.10: Addition of Alcohols WWU Chemistry

23. Formation of Acetals WWU Chemistry

24. A popular acetal! WWU Chemistry

25. Sect. 16.11: Protective groups WWU Chemistry

26. Sect. 16.12: Addition-Elimination:The Formation of Imines WWU Chemistry

27. Formation of Simple Imines WWU Chemistry

28. Formation of Oximes an oxime hydroxylamine WWU Chemistry

29. Formation of Hydrazones a hydrazine WWU Chemistry

30. 2,4-Dinitrophenylhydrazones 2,4-dinitrophenylhydrazine WWU Chemistry

31. Formation of Semicarbazones semicarbazide WWU Chemistry

32. Addition-Elimination:The Formation of Imines WWU Chemistry

33. Sect. 16.13: Formation of Enamines WWU Chemistry

34. Enamine Formation (Part One) WWU Chemistry

35. Enamine Formation (Part Two) WWU Chemistry

36. Nucleophilic Characterof Enamines WWU Chemistry

37. Reactions of Enaminesas Nucleophiles WWU Chemistry

38. Hydrolysis of Iminium Salts(Part One) WWU Chemistry

39. Hydrolysis of Iminium Salts(Part Two) WWU Chemistry

40. Enamine Reactions -- Summary WWU Chemistry

41. Gilbert Stork, developed enamine chemistry and also did a total synthesis of Quinine C & E News, 26 Feb, 2007 WWU Chemistry

42. Source of picture: Michigan State University, Department of Chemistry http://www.chemistry.msu.edu/Portraits/PortraitsHH_collection.shtml Quinine has four stereocenters! WWU Chemistry

43. William Doering (left) and R.B. Woodward, Harvard, synthesized precursor to quinine, 1944. Notice the cigarette! Woodward won the Nobel Prize in 1965. WWU Chemistry

44. Woodward (left) and Doering discussing the synthesis of quinine. WWU Chemistry

45. K. B. Wiberg, Yale University, Lampman’s Ph.D. adviser. Wiberg was a Ph.D. student of Doering. WWU Chemistry

46. Lampman chemical genealogy WWU Chemistry

47. Gabrielle Fallopio WWU Chemistry

48. Justus von Liebig WWU Chemistry

49. August Wilhelm von Hofmann WWU Chemistry

50. Lampman chemical genealogy WWU Chemistry