1. Enols and Enolates  Substitutions and Condensations of Ketones and Aldehydes

2. Tautomerization Accelerated in Acid

3.  -Halogenation

4. Reaction Occurs via Enol

5. Tautomerization Acceleration in Base

6. Alkylation in Base Reaction with 1 o RX

8. Using LDA as Base to form Enolate

9. Alkylation  to C=O C-alkylation preferred

10. Alkylation Occurs on Less Hindered Side of C=O

11. Malonic Ester Synthesis of Carboxylic Acids

12. H’s are unusually acidic

14. Decarboxylation (loss of CO 2 )

15. 2 Acidic  H’s, 2 Alkylations; Determine the Product of the Synthesis

16. All  -keto acids are unstable and Decarboxylate

17. Enamines can be Alkylated

18. Alkylation of an Enamine  Position is Activated

19. Complements LDA Reaction

20. LDA vs. Enamine Reaction

21.  Selenation: Formation of  -Unsaturated Ketones

22. Mechanism

23. Synthesis

25. Aldol Condensation

26. Enolate Undergoes Nucleophilic Addition

27. Aldol Condensation Dimerization of 3-Pentanone

28. Crossed Aldol Between 2 Different C=O Compounds

29. Four Possible Condensation Products

30. Crossed Aldol Condensation

31. Dehydration of Aldol Products

32. Predicting Aldol Dehydration Products

34. Intramolecular Aldol

35. Predict the Product

37. Conjugate Addition

38. 1,2 - vs. 1,4 - Addition

39. Michael Addition Conjugate Addition of Enolate to  - Unsaturated Ketone

40. Robinson Annulation: Michael Addition followed by Aldol Consensation