1 / 24

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.

major
Download Presentation

Chapter 20: Carboxylic Acid Derivatives - NAS

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. 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

More Related