VJC 2025 CAD Lecture Notes

1 VICTORIA JUNIOR COLLEGE CHEMISTRY DEPARTMENT JC2 H2 CHEMISTRY CARBOXYLIC ACIDS & DERIVATIVES _______________________________________________________________________________ Lecture Outline Part I: Carboxylic Acids 1 Introduction 2 Physical Properties 2.1 Boiling Point 2.2 Solubility 2.3 Acidity 3 Laboratory Preparation 3.1 Oxidation of Primary Alcohols and Aldehydes 3.2 Hydrolysis of Nitriles 3.3 Benzoic Acid Formation from Alkylbenzene 4 Reactions 4.1 Salt Formation 4.2 Condensation to form Ester 4.3 Conversion to Acyl Chlorides 4.4 Reduction to Primary Alcohols 4.5 Decarboxylation to Alkanes 5 Special Reactions (Dehydration and Oxidation) 5.1 Methanoic Acid 5.2 Ethanedioic Acid 6 Summary of Reactions of Carboxylic Acids Part II: Acid Derivatives (Esters and Acyl Chlorides) 1 Introduction 2 Physical Properties 2.1 Boiling Point 2.2 Solubility 3 Reactions 3.1 Esters 3.1.1 Hydrolysis 3.2 Acyl Chlorides 3.2.1 Hydrolysis 3.2.2 Condensation with Alcohols and Phenols to form Esters 3.2.3 Condensation with Ammonia and Amines to form Amides 4 Summary of Reactions of Acid Derivatives Lesson 1 2 Pages 1 – 14 15 – 20 Complete by 30 Mar 30 Mar scan this QR code to ask questions related to the lecture

2 Assessment Objectives Students should be able to: (a) Describe the formation of carboxylic acids from alcohols, aldehydes and nitriles (b) Describe the reactions of carboxylic acids in the formation of: (i) salts (ii) esters on condensation with alcohols, using ethyl ethanoate as an example (iii) acyl chlorides, using ethanoyl chloride as an example (iv) primary alcohols, via reduction with lithium aluminium hydride, using ethanol as an example (c) Explain the acidity of carboxylic acids and of chlorine –substituted ethanoic acids in terms of their structures (d) Describe the hydrolysis of acyl chlorides (e) Describe the condensation reactions of acyl chlorides with alcohols, phenols and primary amines (f) Explain the relative ease of hydrolysis of acyl chlorides, alkyl chlorides and aryl chlorides (g) Describe the formation of esters from the condensation reaction of acyl chlorides, using phenyl benzoate as an example (h) Describe the acid and base hydrolysis of esters References (a) Introduction to Organic Chemistry by GI Brown (b) Principles of Organic Chemistry by Peter RS Murray (c) Organic Chemistry by Morrison and Boyd (d) Organic Chemistry by TW Graham Solomons

3 Part I: Carboxylic Acids 1 Introduction Structure • General formula of monocarboxylic acids is CnH2nO2 • Functional group is a carboxyl functional group, –COOH or –CO2H, which contains both a carbonyl group and a hydroxyl group; hence the name. • Carboxylic acids are represented as RCO2H, where R = H, alkyl or aryl group. Nomenclature 1. find the longest alkyl chain, which is the parent chain, that contains the carboxyl group 2. the ‘e’ of the –ane of the alkan