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ALDEHYDES AND KETONES I. Nucleophilic Addition to Carbonyl

ALDEHYDES AND KETONES I. Nucleophilic Addition to Carbonyl. Chapter 16. Reading Assignment. SKIP: Section 16.8 SKIP: Section 16.19 I will be covering the remaining sections. Problem Assignment. In-Text Problems 16.1 and 2 3 (except for d) 5 - 10 12 - 18 21 - 25

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ALDEHYDES AND KETONES I. Nucleophilic Addition to Carbonyl

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  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

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