1. Natural Products Nomenclature Acidity Preparation Reactions
Carboxylic Acids
Natural Products
Nomenclature
Acidity
Preparation
Reactions

2. Analgesics

3. Fats and Fatty Acids

4. Prostaglandins

5. Penicillins from mold

6. From Ergot Fungus

7. Common Nomenclature

9. I.U.P.A.C. Nomenclature

10. Dicarboxylic Acids

11. A Diacid

12. Unusually High Melting and Boiling Points

13. Boiling Points

14. Acidity is due to Delocalization of the Charge in the Conjugate Base

15. Alcohol vs. Acid

16. e- Withdrawing Groups Enhance Acidity

17. Benzoic acids

18. Deprotonation

19. Carboxylic Acid Preparations
Oxidation of 1o alcohols and aldehydes with Na2Cr2O7/H2SO4
KMnO4 oxidation of alkylbenzenes
Grignard reaction with CO2 (Carboxylation)
Hydrolysis of a carboxylic derivative:
e.g. acid chloride, acid anhydride, ester, amide, nitrile

20. Grignard Reaction with CO2

21. Mechanism

22. Hydrolysis of a Nitrile

23. Reduction of Carboxylic Acids

24. Carboxylic Acid Derivatives
Acid Chlorides
Acid Anhydrides
Esters
Amides
Nitriles
Nucleophilic Acyl Substitution

26. Reactivity of Acid Derivatives

28. I.U.P.A.C. Nomenclature (uses carboxylic acid template)

29. Acid Chlorides

30. Acid Anhydrides

31. Esters

32. Amides

33. Lactones (cyclic esters)

34. Gamma Hydroxybutyrate

35. All Acid Derivatives can be Hydrolyzed

36. What are the 3 Hydrolysis Products?

38. Draw the Hydrolysis Products

39. Hydrolysis of Penicillin

40. Aspartame

41. Nucleophilic Acyl Substitution

42. Nucleophilic Acyl Substitution

43. Hydrolysis of an Acid Chloride

44. Acid Chloride Preparation

46. With Acid Chlorides, No Catalyst is Needed Anhydride Prep.

48. Ester Preparation from an acid chloride

49. Amide Preparation from an Acid Chloride

50. Amide from Anhydride

51. Fischer Esterification

52. Flavors and Fragrances

53. Intramolecular Fischer Esterification - GHB

55. Lactam (cyclic amide) Formation

56. b-Lactams as Antibiotics

57. Acid Catalyzed “Olysis” Reactions

58. Transesterification a Methanolysis

60. Aspirin Synthesis

62. Basic Hydrolysis Saponification

63. Basic Hydrolysis of an Amide

64. Mechanism

66. Reduction of Esters with LiAlH4

67. DIBAH Diisobutyl Aluminum Hydride