Contents 84 Keto-enol tautomerism Reactivity of enols Acidity of a-hydrogen atoms:enolate ion formation 8.4.4 Reactivity of enolates 1555151580 85 Carbonyl-carbonyl condensation reactions 8.5.1 Condensations of aldehydes and ketones: the aldol condensation reaction 8.52 Crossed or mixed aldol condensations 18 8.53 Intramolecular aldol reactions 8.5.4 The Michael reaction Worked example Problems 6116 0 nds:carboxylic acids and derivatives 9.3 acyl substitutior reactions 66666 acid derivatives derivatives arboxylc acids 169 9.3.3 ersus 9.4 Preparation of esters (esterification) Nucleophilic substitution reactions of acid chloride Nucleophilic substitution reactions of acid anhydrides 9.7 Nucleophilic substitution reactions of esters 9.8 Nucleophilic substitution and reduction reactions of amides Nucleophilic addition reactions of nitriles 9.10 a-Substitution reactions of carboxylic acids 9.11 Carbonyl-carbonyl condensation reactions 9.11.1 The Claisen condensation reaction 9 Crossed or mixed Claisen condensations 18 Intramolecular Claisen condensations: the Dieckmann reaction 9.12 A summary of carbonyl reactivity Worked example Problems 10 10. spectrometry (MS) 10. Introduction 10.1 10.1.3 Determination of molecular formula 8.4 a-Substitution reactions 156 8.4.1 Keto-enol tautomerism 156 8.4.2 Reactivity of enols 157 8.4.3 Acidity of a-hydrogen atoms: enolate ion formation 157 8.4.4 Reactivity of enolates 158 8.5 Carbonyl-carbonyl condensation reactions 160 8.5.1 Condensations of aldehydes and ketones: the aldol condensation reaction 160 8.5.2 Crossed or mixed aldol condensations 161 8.5.3 Intramolecular aldol reactions 162 8.5.4 The Michael reaction 163 Worked example 164 Problems 165 9 Carbonyl compounds: carboxylic acids and derivatives 167 9.1 Structure 167 9.2 Reactivity 168 9.3 Nucleophilic acyl substitution reactions 168 9.3.1 Relative reactivity of carboxylic acid derivatives 168 9.3.2 Reactivity of carboxylic acid derivatives versus carboxylic acids 169 9.3.3 Reactivity of carboxylic acid derivatives versus aldehydes/ketones 169 9.4 Nucleophilic substitution reactions of carboxylic acids 170 9.4.1 Preparation of acid chlorides 170 9.4.2 Preparation of esters (esterification) 170 9.5 Nucleophilic substitution reactions of acid chlorides 171 9.6 Nucleophilic substitution reactions of acid anhydrides 172 9.7 Nucleophilic substitution reactions of esters 173 9.8 Nucleophilic substitution and reduction reactions of amides 175 9.9 Nucleophilic addition reactions of nitriles 176 9.10 a-Substitution reactions of carboxylic acids 178 9.11 Carbonyl-carbonyl condensation reactions 178 9.11.1 The Claisen condensation reaction 178 9.11.2 Crossed or mixed Claisen condensations 179 9.11.3 Intramolecular Claisen condensations: the Dieckmann reaction 180 9.12 A summary of carbonyl reactivity 181 Worked example 182 Problems 183 10 Spectroscopy 185 10.1 Mass spectrometry (MS) 185 10.1.1 Introduction 185 10.1.2 Isotope patterns 187 10.1.3 Determination of molecular formula 188 viii Contents