Exploring Functional Derivatives of Carboxylic Acids: Halides, Esters, Amides, Lactones, a, Study notes of Organic Chemistry

Download Exploring Functional Derivatives of Carboxylic Acids: Halides, Esters, Amides, Lactones, a and more Study notes Organic Chemistry in PDF only on Docsity! 1 Chapter 15. Functional Derivatives of Carboxylic Acids Learning objectives: 1. Recognize the names and structures for the following functional groups: acid halide, acid anhydride, ester, amide, lactone, and lactam. 2. Write the general electron-pushing (arrow-pushing) mechanisms for the nucleophilic acyl substitution of acid halide, acid anhydride, ester, and amide. 3. Explain the order of reactivity toward nucleophilic acyl substitution among acid halide, acid anhydride, ester, and amide based on the pKa of the conjugate acid of the leaving groups on these four acid derivatives. 4. Provide appropriate reagents and reaction conditions for the feasible interconversions among acid halide, acid anhydride, carboxylic acid, ester, and amide. Sections to be covered (in the order of delivery): 15.1 Introduction # 15.2 Structure and Nomenclature 15.3 Characteristic Reactions * 15.4 Reaction with Water – Hydrolysis * 15.5 Reaction with Alcohols * 15.6 Reaction with Ammonia and Amines * 15.7 Interconversion of Functional Derivatives * 15.8 Esters with Grignard Reagents * 15.9 Reduction * Sections that will be focused # Sections that will be skipped Recommended additional problems 15.8 – 15.43 2 15.2 Structure and Nomenclature A. Ethanoyl Chloride (Acyl Halides) B. Acid Anhydrides C. Esters and Lactones D. Amides and Lactams 5 C. Esters (i) In Acidic Condition (i) In Basic Condition 6 D. Amides 15.5 Reaction with Alcohols A. Acid Chlorides (Acyl Chlorides) B. Acid Anhydrides 7 C. Esters D. Amides 15.6 Reaction with Ammonia and Amines A. Acid Chlorides (Acyl Chlorides) 10 15.8 Esters with Grignard Reagents A. Example O OCH3 1) CH3CH2MgBr (2 equivalents) 2) HCl, H2O B. Mechanism 15.9 Reduction A. Esters 11 B. Amides