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CHAPTER 19 Carboxylic Acids

2. Substitution at the Carboxy Carbon: The Addition-Elimination Mechanism. 19-7. The carbonyl carbon is attacked by nucleophiles.Carboxylic acids and their derivatives of the form RCOL can be attacked by nucleophiles.. Unlike the reactions with aldehydes and ketones, the attacking nucleophile disp

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CHAPTER 19 Carboxylic Acids

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    1. 1 CHAPTER 19 Carboxylic 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 Alcohols by Lithium Aluminum Hydride 40

    41. Example 41

    42. End 42

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