1. 1 CHAPTER 19Carboxylic Acids

2. 2 Substitution at the Carboxy Carbon: The Addition-Elimination Mechanism

3. 3 The attacking nucleophile displaces the leaving group resulting in an addition-elimination reaction.

4. 4

5. 5

6. 6

7. 7

8. 8

9. Acid Catalyzed Addition-elimination 9

10. 10

11. 11

12. 12 Competing Reactions of a carboxylic acid with a Nucleophile

13. Esterification Reaction Carboxylic Acid + Alcohol = Ester + water RCOOH + HOR1 = RCOOR1 + H2O CH3COOH + HOCH2CH3 = CH3COOCH2CH3 + H2O 13

14. 14

15. 15 Carboxylic Acid Derivatives: Alkanoyl (Acyl) Halides

16. 16 Alkanoyl (Acyl) Halide Synthesis

17. 17

18. 18

19. 19

20. 20

21. 21

22. 22 Because the halogen in an alkanoyl halide and the RCO2 group in an anhydride are good leaving groups, alkanoyl halides and anhydrides are often useful intermediates during the preparation of other compounds.

23. 23 Carboxylic Acid Derivatives: Esters

24. 24 Carboxylic Acid Derivatives: Esters

25. 25

26. 26

27. 27 Mechanism of Acid-Catalyzed Exterification

28. 28 Mechanism of Acid-Catalyzed Exterification

29. 29 Mechanism of Acid-Catalyzed Exterification

30. 30 Mechanism of Acid-Catalyzed Exterification

31. 31

32. 32

33. 33 Cyclic esters are called - Lactones

34. 34 Carboxylic Acid Derivatives: Amides

35. 35 The ammonium carboxylate salt is very resistant to nucleophilic attack.

36. 36

37. 37

38. 38

39. 39

40. Carboxylic Acids Reduced to Alcoholsby Lithium Aluminum Hydride 40

41. Example 41

42. End 42