xiv Contents 17-6 Activating.Ortho.Para-Directing Substituents 766 Summary:Activating.Ortho.Para-Directors 768 17-7 Deactivating.Meta-Directing Substituents 769 Summary:Deactivating,Meta-Directors 771 17-8 Halo en Substituents:Deactivating,but Ortho, Para-Directing 772 Summary:Directing Effects of Substituents 774 17-9 oMu Substituentson Electrophilic Aromatic 17.10 The Friedel-Crafts Alkylation 777 Mechanism 17-5:Friedel-Crafts Alkylation 778 17.11 The Friedel-Crafts Acylation 781 Mechanism 17-6 Friedel-Crafts Acvlation 782 -Akyaion and 17-12 Nucleophilic Aromatic Substitution 786 Mechanism 17-8:Nucle 17-13 Aromatic Substitutions Using Organometallic Reagents 790 17-14 Addition Reactions of Benzene Derivatives 796 Mechanism 17-9:The Birch Reduction 797 17.15 Side-Chain Reactions of Benzene Derivatives 798 17-16 Reactions of Phenols 802 Summary:Reactions of Aromatic Compounds 805 Essentia Study Problems 810 18 KETONES AND ALDEHYDES 816 18-1 Carbonyl Compounds 816 18-2 Structure of the Carbonyl Group 817 18-3 Nomen clature of Ketones and Aldehydes 818 Physical Properties of Ketones and Aldehydes 820 Spectroscopy of Ketones and Aldehydes 822 eny 828 0 tones trom Carbo: and nydes 833 18-10 and Esters 835 Summary:Syntheses of Ketones and Aldehydes 837 18-11 Reactions of Ketones and Aldehydes:Introduction to 1on839 ey leophilic Additions to Carbonyl Groups 841 18-12 1on843 2:The Wittig Reaction 18-13 Hydration ones and Al ebydes847 tones and Aldehydes 847 17-6 Activating, Ortho, Para-Directing Substituents 766 Summary: Activating, Ortho, Para-Directors 768 17-7 Deactivating, Meta-Directing Substituents 769 Summary: Deactivating, Meta-Directors 771 17-8 Halogen Substituents: Deactivating, but Ortho, Para-Directing 772 Summary: Directing Effects of Substituents 774 17-9 Effects of Multiple Substituents on Electrophilic Aromatic Substitution 774 17-10 The Friedel–Crafts Alkylation 777 Mechanism 17-5: Friedel–Crafts Alkylation 778 17-11 The Friedel–Crafts Acylation 781 Mechanism 17-6: Friedel–Crafts Acylation 782 Summary: Comparison of Friedel–Crafts Alkylation and Acylation 784 17-12 Nucleophilic Aromatic Substitution 786 Mechanism 17-7: Nucleophilic Aromatic Substitution (Addition–Elimination) 787 Mechanism 17-8: Nucleophilic Aromatic Substitution (Benzyne Mechanism) 789 17-13 Aromatic Substitutions Using Organometallic Reagents 790 17-14 Addition Reactions of Benzene Derivatives 796 Mechanism 17-9:The Birch Reduction 797 17-15 Side-Chain Reactions of Benzene Derivatives 798 17-16 Reactions of Phenols 802 Summary: Reactions of Aromatic Compounds 805 Essential Terms 808 Study Problems 810 18 KETONES AND ALDEHYDES 816 18-1 Carbonyl Compounds 816 18-2 Structure of the Carbonyl Group 817 18-3 Nomenclature of Ketones and Aldehydes 818 18-4 Physical Properties of Ketones and Aldehydes 820 18-5 Spectroscopy of Ketones and Aldehydes 822 18-6 Industrial Importance of Ketones and Aldehydes 828 18-7 Review of Syntheses of Ketones and Aldehydes 829 18-8 Synthesis of Ketones from Carboxylic Acids 833 18-9 Synthesis of Ketones and Aldehydes from Nitriles 833 18-10 Synthesis of Aldehydes and Ketones from Acid Chlorides and Esters 835 Summary: Syntheses of Ketones and Aldehydes 837 18-11 Reactions of Ketones and Aldehydes: Introduction to Nucleophilic Addition 839 Key Mechanism 18-1: Nucleophilic Additions to Carbonyl Groups 841 18-12 The Wittig Reaction 843 Mechanism 18-2: The Wittig Reaction 844 18-13 Hydration of Ketones and Aldehydes 847 Mechanism 18-3: Hydration of Ketones and Aldehydes 847 xiv Contents