xiv Organic Chemistry ll For Dummies Chapter 8:Aromatic Substitution Part ll:Attack of the Nucleophiles and Other Reactions.........................111 Coming back to nucleophilic substitution reactions 111 Mastering the Mechanisms of Nucleophilic Substitution Reactions....112 Losing and Gaining:Mechanisms of Elimination/Addition Reactions 114 Benzyne.... 114 The elimination/addition mechanism. .114 Synthetic Strategies for Making Aromatic Compounds....... 115 Briefly Exploring Other Reactions........ .117 Part 111:Carbonyls:Good Alcohols Gone Bad. .121 Chapter 9:Comprehending Carbonyls 123 Carbonyl Basics........ .123 Considering compounds containing the carbonyl group...........124 Getting to know the acidic carbonyl.. 12 Polarity of Carbonyls Resonance in Donyls Reactivity of th onyl Group Spectros yof Ca bonyls 12 iole ble(el eti e (NMRO opy 12 Mass spectro .134 Chapter 10:Aldehydes and Ketones. .....137 enclature. op Creatin hydes s and Ker tones with Synthesis Reactions 140 eactions 1A Other reactions 142 Taking Them a Step Further:Reactions of Aldehydes and Ketones...146 Nucleophilic attack of aldehydes and ketones 147 Oxidation of aldehydes and ketones. 156 The Baeyer-Villiger reaction. .158 Checking Out Spectroscopy Specs. .160 Chapter 11:Enols and Enolates................................161 Getting to Know Enols and Enolates 161 eady:Structu re of enols and enolates 16 ght I saw a tautom 163 Studying the Synthesis of Enols and Enolates. .164xiv Organic Chemistry II For Dummies Chapter 8: Aromatic Substitution Part II: Attack of the Nucleophiles and Other Reactions . . . . . . . . . . . . . . . . . . . . . . . . .111 Coming Back to Nucleophilic Substitution Reactions ............................111 Mastering the Mechanisms of Nucleophilic Substitution Reactions ....112 Losing and Gaining: Mechanisms of Elimination/Addition Reactions...................................................................................................114 Benzyne ...............................................................................................114 The elimination/addition mechanism .............................................114 Synthetic Strategies for Making Aromatic Compounds ..........................115 Briefl y Exploring Other Reactions .............................................................117 Part III: Carbonyls: Good Alcohols Gone Bad .............. 121 Chapter 9: Comprehending Carbonyls . . . . . . . . . . . . . . . . . . . . . . . . . .123 Carbonyl Basics ...........................................................................................123 Considering compounds containing the carbonyl group .............124 Getting to know the acidic carbonyl ...............................................127 Polarity of Carbonyls ..................................................................................128 Resonance in Carbonyls .............................................................................129 Reactivity of the Carbonyl Group ..............................................................130 Spectroscopy of Carbonyls ........................................................................130 Infrared spectroscopy .......................................................................130 Ultraviolet-visible (electronic) spectroscopy ................................131 Nuclear magnetic resonance (NMR) spectroscopy.......................132 Mass spectroscopy ............................................................................134 Chapter 10: Aldehydes and Ketones . . . . . . . . . . . . . . . . . . . . . . . . . . . .137 Meeting Alcohol’s Relatives: Structure and Nomenclature ...................137 Defi ning Physical Properties of Aldehydes and Ketones .......................139 Creating Aldehydes and Ketones with Synthesis Reactions ..................140 Oxidation reactions ...........................................................................140 Reduction reactions ..........................................................................142 Other reactions ..................................................................................143 Taking Them a Step Further: Reactions of Aldehydes and Ketones .....146 Nucleophilic attack of aldehydes and ketones ..............................147 Oxidation of aldehydes and ketones ...............................................156 The Baeyer-Villiger reaction .............................................................158 Checking Out Spectroscopy Specs ............................................................160 Chapter 11: Enols and Enolates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .161 Getting to Know Enols and Enolates .........................................................161 Enough already: Structure of enols and enolates ..........................162 I thought I saw a tautomer ................................................................163 Studying the Synthesis of Enols and Enolates .........................................164 02_178157-ftoc.indd xiv 5/28/10 9:44 AM