X CONTENTS CHAPTER 4 GEOMETRY 76 4.1 Orbitals and Hybridization States 76 4.2 Geometry 80 CHAPTER 5 NOMENCLATURE 84 5.1 Functional Group 85 5.2 Unsaturation 5.3 Naming the Parent Chain 89 5.4 Naming Substituents 91 5.5 Stereoisomerism 95 5.7 Comn 103 5.8 Going from a Name to a Structure 104 CHAPTER 6 CONFORMATIONS 106 6.1 How to Draw a Newman Projection 107 6.2 Ranking the Stability of Newman Projections 111 6.3 Drawing Chair Conformations 115 6.4 Placing Groups on the Chair 118 6.5 Ring Flipping 123 6.6 Com 129 133 CHAPTER 7 CONFIGURATIONS 134 7.1 Locating Stereocenters 135 7.2 Determining the Configuration of a Stereocenter 138 7.3 Nomenclature 146 7.4 Drawing Enantiomers 151 75 Diastereomers 156 7.6 Meso Co unds 157 7.8 Optical Activity 165 CHAPTER 8 MECHANISMS 167 8.1 Curved Arrows 168 8.2 Arrow Pushing 173 8.3 Drawing Intermediates 175 8.4 Nucleophiles and Electrophiles 178 8.5 Bases Versus Nucleophiles 179 8.6 The Regiochemistry Is Contained Within the Mechanism 182CHAPTER 4 GEOMETRY 76 4.1 Orbitals and Hybridization States 76 4.2Geometry 80 CHAPTER 5 NOMENCLATURE 84 5.1 Functional Group 85 5.2Unsaturation 87 5.3 Naming the Parent Chain 89 5.4 Naming Substituents 91 5.5 Stereoisomerism 95 5.6 Numbering 98 5.7 Common Names 103 5.8 Going from a Name to a Structure 104 CHAPTER 6 CONFORMATIONS 106 6.1 How to Draw a Newman Projection 107 6.2Ranking the Stability of Newman Projections 111 6.3 Drawing Chair Conformations 115 6.4 Placing Groups on the Chair 118 6.5 Ring Flipping 123 6.6 Comparing the Stability of Chairs 129 6.7 Don’t Be Confused by the Nomenclature 133 CHAPTER 7 CONFIGURATIONS 134 7.1 Locating Stereocenters 135 7.2Determining the Configuration of a Stereocenter 138 7.3 Nomenclature 146 7.4 Drawing Enantiomers 151 7.5 Diastereomers 156 7.6 Meso Compounds 157 7.7 Drawing Fischer Projections 160 7.8 Optical Activity 165 CHAPTER 8 MECHANISMS 167 8.1 Curved Arrows 168 8.2Arrow Pushing 173 8.3 Drawing Intermediates 175 8.4 Nucleophiles and Electrophiles 178 8.5 Bases Versus Nucleophiles 179 8.6 The Regiochemistry Is Contained Within the Mechanism 182 x CONTENTS 6753_Klein_00.qxd 5/1/07 5:02 PM Page x