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

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

3. WWU Chemistry Problem Assignment In-Text Problems 16.1 and 2 3 (except for d) 5 - 1012 - 18 21 - 25 End-of-Chapter 1 3 - 5 7 (all but b) 8 b, c, d 1012

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

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

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

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

8. WWU Chemistry 5-bromo-2-methylacetophenone

9. WWU Chemistry Some Common Names of ketones

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

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

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

13. WWU Chemistry 3,4-dibromobenzaldehyde

14. WWU Chemistry Some common names of aldehydes

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

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

17. WWU Chemistry Sect. 16.6: Addition of Cyanide

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

19. WWU Chemistry Synthesis of Alcohols using Grignard reagents - revisited ketonetertiar y alcohol

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

21. WWU Chemistry Sect. 16.9: Addition of Water

22. WWU Chemistry Sect. 16.10: Addition of Alcohols

23. WWU Chemistry Formation of Acetals

24. WWU Chemistry A popular acetal!

25. WWU Chemistry Sect. 16.11: Protective groups

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

27. WWU Chemistry Formation of Simple Imines

28. WWU Chemistry Formation of Oximes hydroxylamine an oxime

29. WWU Chemistry Formation of Hydrazones a hydrazine

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

31. WWU Chemistry Formation of Semicarbazones semicarbazide

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

33. WWU Chemistry Sect. 16.13: Formation of Enamines

34. WWU Chemistry Enamine Formation (Part One)

35. WWU Chemistry Enamine Formation (Part Two)

36. WWU Chemistry Nucleophilic Character of Enamines

37. WWU Chemistry Reactions of Enamines as Nucleophiles

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

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

40. WWU Chemistry Enamine Reactions -- Summary

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

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

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

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

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

46. WWU Chemistry Lampman chemical genealogy

47. WWU Chemistry Gabrielle Fallopio

48. WWU Chemistry Justus von Liebig

49. WWU Chemistry August Wilhelm von Hofmann

50. WWU Chemistry Lampman chemical genealogy

51. WWU Chemistry Sect. 16.14: The Wittig Reaction

52. WWU Chemistry Ylide A compound or intermediate with both a positive and a negative formal charge on adjacent atoms.

53. WWU Chemistry Resonance in Ylides

54. WWU Chemistry Mechanism

55. WWU Chemistry Preparation of the Ylide

56. WWU Chemistry George Wittig, nobel prize, 1979

57. WWU Chemistry Carbohydrates Sections 16.15 - 16.18

58. WWU Chemistry Emil Fischer Source: Michigan State University, Department of Chemistry http://www.chemistry.msu.edu/Portraits/PortraitsHH_collection.shtml

59. WWU Chemistry Norman Haworth Source: Michigan State University, Department of Chemistry http://www.chemistry.msu.edu/Portraits/PortraitsHH_collection.shtml

60. WWU Chemistry Sect. 16.15: Cyclization of Monosaccharides

61. WWU Chemistry Alpha D(+) glucose

62. WWU Chemistry Beta D(+) glucose

63. WWU Chemistry Mutarotation of Glucose

64. WWU Chemistry  -1,4-Glycosidic Linkage

65. WWU Chemistry  -1,4-Glycosidic Linkage

66. WWU Chemistry Sucrose