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Chapter 19: Carboxylic Acids

Chapter 19: Carboxylic Acids. 19.1 – Carboxylic Acid Nomenclature. 19.1 – Carboxylic Acid Nomenclature. 19.2 – Structure and Bonding. Fig. 19.1. 19.3 – Physical Properties. Carboxylic acids are fairly polar compounds and are capable of intermolecular H-bonding:. Fig. 19.2.

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Chapter 19: Carboxylic Acids

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  1. Chapter 19: Carboxylic Acids

  2. 19.1 – Carboxylic Acid Nomenclature

  3. 19.1 – Carboxylic Acid Nomenclature

  4. 19.2 – Structure and Bonding Fig. 19.1

  5. 19.3 – Physical Properties Carboxylic acids are fairly polar compounds and are capable of intermolecular H-bonding: Fig. 19.2

  6. 19.4 – Acidity of Carboxylic Acids Fig. 19.3

  7. 19.5 – Salts of Carboxylic Acids

  8. 19.5 – Salts of Carboxylic Acids A micelle - Figure 19.5

  9. The lipid bilayer – organization of detergents

  10. 19.6 – Substituents and Acid Strength Electron-withdrawing carboxyl group and stabilized anion contribute to acidity (pKa < 5) pKa = 2.9 pKa = 4.0 pKa = 4.5

  11. 19.7 – 19.9 – Substituents and Acid Strength pKa = 4.2 pKa = 2.9 pKa = 2.2

  12. 19.10 – Sources of Carboxylic Acids Fig. 19.6

  13. 19.11 – 19.12 – Synthesis of Carboxylic Acids

  14. 19.13 – Previous Reactions of Carboxylic Acids

  15. 19.14 – Acid-Catalyzed Esterification In experiments with labeled alcohols, the label ends up in the ester – indication of mechanistic pathway

  16. 19.15 – Intramolecular Ester Formation – Lactones Erythromycin – macrolide antibiotic

  17. 19.16 – a-Halogenation of Carboxylic Acids the Hell-Volhard-Zelinsky Reaction

  18. 19.17 – Decarboxylation of Malonic Acid Derivitives

  19. 19.17 – Decarboxylation of Malonic Acid Derivitives

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