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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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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
19.4 – Acidity of Carboxylic Acids Fig. 19.3
19.5 – Salts of Carboxylic Acids A micelle - Figure 19.5
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
19.7 – 19.9 – Substituents and Acid Strength pKa = 4.2 pKa = 2.9 pKa = 2.2
19.10 – Sources of Carboxylic Acids Fig. 19.6
19.14 – Acid-Catalyzed Esterification In experiments with labeled alcohols, the label ends up in the ester – indication of mechanistic pathway
19.15 – Intramolecular Ester Formation – Lactones Erythromycin – macrolide antibiotic
19.16 – a-Halogenation of Carboxylic Acids the Hell-Volhard-Zelinsky Reaction