Carboxylic Acids: Properties, Reactions, and Mechanisms - Prof. Cheng-Wei T. Chang, Study notes of Organic Chemistry

Download Carboxylic Acids: Properties, Reactions, and Mechanisms - Prof. Cheng-Wei T. Chang and more Study notes Organic Chemistry in PDF only on Docsity! 1 Chapter 14. Carboxylic Acids Learning objectives: 1. Provide both IUPAC and common names carboxylic acids. 2. Recognize the physical properties of for carboxylic acids. 3. Recognize the reagents and conditions for the following reactions: reagents for the reduction of carboxylic acids to alcohols and transformation of carboxylic acids to acid chlorides. 4. Write the electron-pushing (arrow-pushing) mechanism for Fisher esterification. 5. Write the electron-pushing (arrow-pushing) mechanism for decarboxylation. Sections to be covered (in the order of delivery): 14.1 Introduction # 14.2 Structure 14.3 Nomenclature 14.4 Physical Properties 14.5 Acidity 14.6 Reduction * 14.7 Fisher Esterification * 14.8 Conversion to Acid Halides * 14.9 Decarboxylation * * Sections that will be focused # Sections that will be skipped Recommended additional problems 14.7 – 14.45 2 14.2 Structure R OH O RCOOH RCO2H 14.3 Nomenclature O OH O OH O OH O OH O OH CO2H CO2H CO2H HO2C 14.4 Physical Properties 5 (ii) Mechanism 14.8 Conversion to Acid Halides A. Use of SOCl2 (PCl3, PBr3) B. Example OH O SOCl2 Cl O SO2 HCl+ ++ 6 14.9 Decarboxylation A. β-Ketoacids (i) General Reaction R OH OO ∆ R O + CO2 (ii) Mechanism B. Malonic Acid and Substituted Malonic Acids HO OH OO ∆ HO O + CO2 R R