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Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution

Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution. Chapter 19. Assignment. Skip the following sections: 19.1, 19.11, 19.15, 19.16, 19.18, 19.21 and 19.32 These PowerPoint slides have been revised for Fall 2007. Some additional sections have been dropped or minimized!.

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Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution

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  1. Carboxylic Acid Derivatives:Nucleophilic Acyl Substitution Chapter 19 WWU-Chemistry

  2. Assignment • Skip the following sections: 19.1, 19.11, 19.15, 19.16, 19.18, 19.21 and 19.32 These PowerPoint slides have been revised for Fall 2007. Some additional sections have been dropped or minimized! WWU-Chemistry

  3. Problem Assignment • In-Text: 1 a, c 4, 5a - d, 6 a - c 8 a, c 9 -11 15 - 19 21 - 23 26, 27 31 - 40 • End-of-Chapter: 4 6 - 9 15 WWU-Chemistry

  4. The addition/elimination mechanism WWU-Chemistry

  5. Nucleophilic Acyl Substitution WWU-Chemistry

  6. Sect. 19.2, 19.3 and 19.4Nomenclature for acid chlorides, acid anhydrides and esters Only ester nomenclature on test! WWU-Chemistry

  7. Acid part of ester Alcohol part of ester WWU-Chemistry

  8. Ethyl ethanoate (IUPAC) Ethyl acetate (common) WWU-Chemistry

  9. Methyl 2-methylpropanoate WWU-Chemistry

  10. Ethyl pentanoate WWU-Chemistry

  11. Methylcyclohexanecarboxylate WWU-Chemistry

  12. Isopropyl benzoate or 2-methylethyl benzoate WWU-Chemistry

  13. Ethyl 5-bromo-3,4-dimethylhexanoate WWU-Chemistry

  14. Ethyl 5-bromo-3,4-dimethyl-2,4-hexadienoate WWU-Chemistry

  15. Sect. 19.5 and 19.6: Nomenclature for amides and nitriles Skip these sections! Not on test! WWU-Chemistry

  16. Sect. 19.7: Mechanisms Base hydrolysis of an ester WWU-Chemistry

  17. Sect. 19.8/ 19.9: Preparation and reactions of acid chlorides Important!!! Acid chlorides are key intermediates for making esters, amides and anhydrides!!!! WWU-Chemistry

  18. Preparation of an Ester WWU-Chemistry

  19. Preparation of an Amide WWU-Chemistry

  20. Preparation of an Anhydride WWU-Chemistry

  21. Sect. 19.10: Reducing agents • Review of reductions on acid chlorides. • A look at the reduction of all the derivatives of carboxylic acids. • We talked about this in Chapter 16! WWU-Chemistry

  22. Reactions of sodium borohydride • Aldehydes yield primary alcohols • Ketones yield secondary alcohols • Esters give no reaction! • Amides give no reaction! WWU-Chemistry

  23. Reactions of lithium aluminum hydride • Aldehydes give primary alcohols • Ketones give secondary alcohols • Esters give primary alcohols from the carboxylic acid part of the ester (Sect 19.20) • Amides give primary amines!! (Sect 19.24) WWU-Chemistry

  24. Sect. 19.11: skip WWU-Chemistry

  25. Sect. 19.12: carboxylic acid derivatives Esters Amides Anhydrides Nitriles All of these functional groups will be hydrolyzed in acidic or basic water to give the parent carboxylic acid WWU-Chemistry

  26. Sect. 19.13 and 9.14: Esters WWU-Chemistry

  27. Esters as Flavoring Substances WWU-Chemistry

  28. Fischer Esterification ESTERIFICATION REACTIONS ARE REVERSIBLE. You need to push it to the right (ester) by removing water as it forms. This reaction is acid catalyzed WWU-Chemistry

  29. Fischer esterification is an acid catalyzed reaction WWU-Chemistry

  30. Sect. 19.15 and 19.16 -- skip WWU-Chemistry

  31. Sect. 19.17: Hydrolysis of Esters See slide for section 19.7 for mechanism of base hydrolysis Mechanism of the acid catalyzed hydrolysis reaction is the reverse of the Fischer esterification reaction! WWU-Chemistry

  32. Sect. 19.18: skip WWU-Chemistry

  33. Sect. 19.19: Reaction of Esters with Organometallic Reagents WWU-Chemistry

  34. Mechanism WWU-Chemistry

  35. Sect. 19.20: Reduction of Esters Lithium aluminum hydride gives the primary alcohol WWU-Chemistry

  36. Diisobutylaluminum hydride (DibalH) gives the aldehyde WWU-Chemistry

  37. Sect. 19.21: skip WWU-Chemistry

  38. Sect. 19.22 and 19.23: Preparation and Reactions of Amides Heat WWU-Chemistry

  39. Remember, also prepare amides from acid chlorides WWU-Chemistry

  40. Amides, continued • Keep this section simple, skip the DCC stuff WWU-Chemistry

  41. Sect. 19.24: Reduction of amides amides give primary amines with lithium aluminum hydride. WWU-Chemistry

  42. Sect. 19.25 and 19.26: Reactions of anhydrides WWU-Chemistry

  43. Preparation of aspirin and acetaminophen (Tylenol) WWU-Chemistry

  44. Sect. 19.27 and 19.28:preparation and reactions of nitriles WWU-Chemistry

  45. Base-Promoted Hydrolysis of a Nitrile (Part One) WWU-Chemistry

  46. Base-Promoted Hydrolysis of a Nitrile (Part Two) WWU-Chemistry

  47. Sect. 19.29: reduction of nitriles with lithium aluminum hydride and Hydrogen WWU-Chemistry

  48. The remaining sections will not be included on the third test. WWU-Chemistry

  49. Sect. 19.30: Fats and oils (Triglycerides) WWU-Chemistry

  50. The Fatty Acids WWU-Chemistry

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