1. Keto-enol tautomerization enolization “normal” aldehydes and ketones K eq = ~ 10 -8

2. Stabilized aldehydes and ketones  -diketones K eq = ~ 10

3. Mechanism for acid-catalyzed enolization

5. Reactions of enols:  -halogenation

6. An example

8. Mechanism of  -halogenation

9.  -Bromination of Acids: the HVZ Reaction

10. The HVZ Reaction

11. Acidity of carbonyl compounds enolate ion formation pK a = ~ 16-20

12. Base-catalyzed enolization

13. Ester Enolates pK a = ~22

14. Alkylation of ester enolates

19. Reactions of enolates: The Aldol Condensation

20. Aldol Condensation

21. More Aldol Condensation

22. Formation of  -unsaturated carbonyls

23. An example

25. Claisen-Schmidt condensation

27. Examples

28. Nucleophilic Addition to  -Unsaturated Carbonyls

29. Michael Addition

31. Robinson Annulation

33. Michael Addition

35. Robinson Annulation

37. The Claisen condensation

39. An example

40. The product

41. Another example

42. Another product

43. The Dieckmann condensation

45. Decarboxylation of Malonic Acids and b-Ketoacids Malonic acidAcetoacetic acid

46. Decarboxylation of Malonic Acids and b-Ketoacids

47. Ketone acylation using esters

50. Acetoacetic ester synthesis of ketones ethyl acetoacetate

51. Acetoacetic ester synthesis of ketones

54. Malonic ester synthesis of acids

55. diethyl malonate

56. Malonic ester synthesis of acids

58. Malonic ester synthesis examples

62. Michael addition

66. Wait! There’s more!

67. Th-th-that’s all, folks.

68. I lied - some cool biochemistry acetyl CoAmalonyl CoA

69. More cool stuff

70. Even more

71. How would you make this?