1 / 53

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!.

dasan
Download Presentation

Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  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

More Related