DETAILED CONTENTS 5 Stereochemistry at Tetrahedral Centers 134 5.1 Enantiomers and the Tetrahedral Carbon 135 52 The Reason for Handedness in Molecules:Chirality 136 Optical Activity140 5.4 Pasteur's Discovery of Enantiomers 142 55 Sequence Rules for Specifying Configuration 143 5.6 Diastereomers 149 57 Meso Compounds 151 5.8 Racemic Mixtures and the Resolution of Enantiomers 154 5.9 A Review of Isomerism 156 5.10 Chirality at Nitrogen,Phosphorus,and Sulfur 158 5.11 Prochirality 159 5.12 Chirality in Nature and Chiral Environments 162 Summary 164 Logniappe-Chiral Drugs 165 Exercises 166 6 An Overview of Organic Reactions 17s 6.1 Kinds of Organic Reactions 176 6.2 How Organic Reactions Occur:Mechanisms 17 6.3 Radical reactions 18 4 Polar Reactions 181 65 An Example of a Polar Reaction:Addition of H2O to Ethylene 186 6. Using Curved Arrows in Polar Reaction Mechanisms 189 67 Describing a Reaction:Equilibria,Rates,and Energy Changes19 6.8 Describing a Reaction:Bond Dissociation Energies19 6.9 Describing a Reaction:Energy Diagrams and Transition States 197 6.10 Describing a reaction:Intermediates 200 6.11 A Comparison between Biological Reactions and Laboratory Reactions 20 Summary 204 Lagniappe-Where Do Drugs Come From?20 Exercises 206 Alkenes and Alkynes 212 7.1 Calculating a Degree of Unsaturation 213 7.2 Naming Alkenes and Alkynes 216 7.3 Cis-Trans Isomerism in Alkenes 219 7.4 Alkene Stereochemistry and the E,Z Designation 221 7.5 Stability of Alkenes 223 viii detailed contents Stereochemistry at Tetrahedral Centers 134 5.1 Enantiomers and the Tetrahedral Carbon 135 5.2 The Reason for Handedness in Molecules: Chirality 136 5.3 Optical Activity 140 5.4 Pasteur’s Discovery of Enantiomers 142 5.5 Sequence Rules for Specifying Configuration 143 5.6 Diastereomers 149 5.7 Meso Compounds 151 5.8 Racemic Mixtures and the Resolution of Enantiomers 154 5.9 A Review of Isomerism 156 5.10 Chirality at Nitrogen, Phosphorus, and Sulfur 158 5.11 Prochirality 159 5.12 Chirality in Nature and Chiral Environments 162 Summary 164 Lagniappe—Chiral Drugs 165 Exercises 166 An Overview of Organic Reactions 175 6.1 Kinds of Organic Reactions 176 6.2 How Organic Reactions Occur: Mechanisms 177 6.3 Radical Reactions 178 6.4 Polar Reactions 181 6.5 An Example of a Polar Reaction: Addition of H2O to Ethylene 186 6.6 Using Curved Arrows in Polar Reaction Mechanisms 189 6.7 Describing a Reaction: Equilibria, Rates, and Energy Changes 192 6.8 Describing a Reaction: Bond Dissociation Energies 195 6.9 Describing a Reaction: Energy Diagrams and Transition States 197 6.10 Describing a Reaction: Intermediates 200 6.11 A Comparison between Biological Reactions and Laboratory Reactions 202 Summary 204 Lagniappe—Where Do Drugs Come From? 205 Exercises 206 Alkenes and Alkynes 212 7.1 Calculating a Degree of Unsaturation 213 7.2 Naming Alkenes and Alkynes 216 7.3 Cis–Trans Isomerism in Alkenes 219 7.4 Alkene Stereochemistry and the E,Z Designation 221 7.5 Stability of Alkenes 223 5 6 7 39144_ FM_i-xxiv.indd viii 8/26/09 10:48:49 AM