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Chapter 20: Carboxylic Acid Derivatives - NAS

Chapter 20: Carboxylic Acid Derivatives - NAS. Carboxylic acid. Acyl (or acid) chloride. Acid anhydride. Ester. Carboxamide. All closely related and made from carboxylic acids most are interconvertable. 20.1 – Carboxylic Acid Derivative Nomenclature. Acyl Chlorides. Acid Anhydrides.

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Chapter 20: Carboxylic Acid Derivatives - NAS

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  1. Chapter 20: Carboxylic Acid Derivatives - NAS Carboxylic acid Acyl (or acid) chloride Acid anhydride Ester Carboxamide • All closely related and made from carboxylic acids • most are interconvertable

  2. 20.1 – Carboxylic Acid Derivative Nomenclature Acyl Chlorides Acid Anhydrides

  3. 20.2 – Carboxylic Acid Derivatives - Structure Extended  system – like carboxylic acids

  4. 20.2 – Structure and Reactivity Fig. 20.2

  5. 20.2 – Structure and Reactivity Resonance possibilities - acid chlorides and anhydrides Acid chlorides and acid anhydrides are not stabilized significantly by resonance – quite reactive towards nucleophiles

  6. 20.2 – Structure and Reactivity Resonance possibilities – esters, amides, carboxylates Increasing delocalization leads to increasing stability and decreasing reactivity

  7. 20.3 – General Mechanism for Nucleophilic Acyl Substitution Tetrahedral intermediate

  8. 20.4 – NAS Using Acid Chlorides

  9. 20.4 – NAS Using Acid Chlorides, e.g. Amide Synthesis Tetrahedral intermediate

  10. 20.5 – Acyl Substitution in Carboxylic Acid Anhydrides Synthesis of anhydrides Acetic anhydride Maleic anhydride

  11. 20.5 – Acyl Substitution in Carboxylic Acid Anhydrides Lab experiment

  12. 20.5 – Acyl Substitution in Carboxylic Acid Anhydrides Lab experiment 3720

  13. 20.5 – Acyl Substitution in Carboxylic Acid Anhydrides 50-75% decrease in S. aureus CP construction Selective inhibitor of endothelial cell proliferation

  14. 20.5 – Acyl Substitution in Carboxylic Acid Anhydrides • “N-Glycoside neoglycotrimers from 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl azide,” D. P. Temelkoff, M. Zeller, and P. Norris, Carbohydr. Res.2006, 341, 1081-1090. • “Application of Bis(diphenylphosphino)ethane in Staudinger-type N-Glycosyl Amide Synthesis,” D. P. Temelkoff, C. R. Smith, D. A. Kibler, S. McKee, S. Duncan, M. Zeller, M. Hunsen, and P. Norris, Carbohydr. Res.2006, 341, 1645-1656.

  15. 20.6 – Sources of Esters

  16. 20.7 – Physical Properties of Esters

  17. 20.10 – Reactions of Esters Acid-catalyzed hydrolysis Basic hydrolysis – saponification

  18. 20.12 – Thioesters Acetyl coenzyme A

  19. 20.13 – Amides Hydrogen bonding

  20. 20.11-13 – Amides – Structure and Synthesis

  21. 20.14 – Intramolecular Amide Formation – Lactams

  22. 20.15 – Hydrolysis of Amides – not covering

  23. 20.16 – 20.17 – Preparation and Hydrolysis of Nitriles • Protonate nitrogen, attack C with water • Proton transfer to nitrogen followed by enolization • Rest of mechanism the same as the amide hydrolysis

  24. 20.18 – Addition of RMgX to Nitriles – Not Covering

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