CONTENTS xi 8.7 The Stereochemistry Is Contained Within the Mechanism 185 8.8 A List of Mechanisms 190 CHAPTER 9 SUBSTITUTION REACTIONS 211 9.1 The Mechanisms 211 9.2 Factor 1-The Electrophile(Substrate)214 9.3 Factor 2-The Nucleophile 217 9.4 Factor 3-The Leaving Group 220 9.5 Factor 4The Solvent 223 9.6 Using All Four Factors 22 9.7 Substitution Reactions Teach Us Some Important Lessons 227 CHAPTER 10 ELIMINATION REACTIONS 229 10.1 Mechanisms(El and E2)230 10.2 Factor 1-The Substrate 231 103 Factor 2-The Base 232 10.4 Factor3-The Leaving Group 35 10.5 Factor4Solvent Effects 36 10.6 Using All of the Factors 236 10.7 Elimination Reactions-Regiochemistry and Stereochemistry 238 CHAPTER 11 ADDITION REACTIONS 242 11.1 Terminology Describing Regiochemistry 242 y Describing Stereochemistry 11.3 Adding H and H 11.4 Adding H and X,Markovnikov 256 11.5 Adding H and Br,Anti-Markovnikov 263 11.6 Adding H and OH,Markovnikov 268 11.7 Adding H and OH,Anti-Markovnikov 272 11.8 Synthesis Techn ques 277 11Adding Br and Br Adding Br and OH 11.10 Adding OH and OH,Anti 290 11.11 Adding OH and OH,Syn 293 11.12 Oxidative Cleavage of an Alkene 296 CHAPTER 12 PREDICTING PRODUCTS 299 12.1 General Tips for Predicting Products 299 12.2G tting Prac 1ce30 12.3 Substitution Versus Elimination Reactions 311 12.4 Looking Forward 315 8.7 The Stereochemistry Is Contained Within the Mechanism 185 8.8 A List of Mechanisms 190 CHAPTER 9 SUBSTITUTION REACTIONS 211 9.1 The Mechanisms 211 9.2Factor 1—The Electrophile (Substrate) 214 9.3 Factor 2—The Nucleophile 217 9.4 Factor 3—The Leaving Group 220 9.5 Factor 4—The Solvent 223 9.6 Using All Four Factors 226 9.7 Substitution Reactions Teach Us Some Important Lessons 227 CHAPTER 10 ELIMINATION REACTIONS 229 10.1 Mechanisms (E1 and E2) 230 10.2Factor 1—The Substrate 231 10.3 Factor 2—The Base 232 10.4 Factor 3—The Leaving Group 235 10.5 Factor 4—Solvent Effects 236 10.6 Using All of the Factors 236 10.7 Elimination Reactions—Regiochemistry and Stereochemistry 238 CHAPTER 11 ADDITION REACTIONS 242 11.1 Terminology Describing Regiochemistry 242 11.2Terminology Describing Stereochemistry 244 11.3 Adding H and H 253 11.4 Adding H and X, Markovnikov 256 11.5 Adding H and Br, Anti-Markovnikov 263 11.6 Adding H and OH, Markovnikov 268 11.7 Adding H and OH, Anti-Markovnikov 272 11.8 Synthesis Techniques 277 11.9 Adding Br and Br; Adding Br and OH 285 11.10 Adding OH and OH, Anti 290 11.11 Adding OH and OH, Syn 293 11.12Oxidative Cleavage of an Alkene 296 CHAPTER 12 PREDICTING PRODUCTS 299 12.1 General Tips for Predicting Products 299 12.2 Getting Practice 300 12.3 Substitution Versus Elimination Reactions 311 12.4 Looking Forward 315 CONTENTS xi 6753_Klein_00.qxd 5/1/07 5:02 PM Page xi