Table of Contents

Introduction 1 Part 1: Getting Started with Organic Chemistry 5 CHAPTER 1: The Wonderful World of Organic Chemistry 7 CHAPTER 2: Dissecting Atoms: Atomic Structure and Bonding 15 CHAPTER 3: Speaking with Pictures: Drawing Structures 35 CHAPTER 4: Covering the Bases (And the Acids) 57 CHAPTER 5: Reactivity Centers: Functional Groups 67 CHAPTER 6: Seeing in 3-D: Stereochemistry 81 Part 2: Hydrocarbons 97 CHAPTER 7: What s in a Name? Alkane Nomenclature 99 CHAPTER 8: Drawing Alkanes 107 CHAPTER 9: Seeing Double: The Alkenes 123 CHAPTER 10: Reactions of Alkenes 137 CHAPTER 11: It Takes Alkynes: The Carbon-Carbon Triple Bond 149 Part 3: Functional Groups 157 CHAPTER 12: Replacing and Removing: Substitution and Elimination Reactions 159 CHAPTER 13: Getting Drunk on Organic Molecules: The Alcohols 175 CHAPTER 14: Side-by-Side: Conjugated Alkenes and the Diels Alder Reaction 183 CHAPTER 15: Lord of the Rings: Aromatic Compounds 193 CHAPTER 16: Bringing Out the Howitzers: Reactions of Aromatic Compounds 209 Part 4: Spectroscopy and Structure Determination 223 CHAPTER 17: A Smashing Time: Mass Spectrometry 225 CHAPTER 18: Seeing Good Vibrations: IR Spectroscopy 241 CHAPTER 19: NMR Spectroscopy: Hold onto Your Hats, You re Going Nuclear! 253 CHAPTER 20: Following the Clues: Solving Problems in NMR 273 Part 5: The Part of Tens 293 CHAPTER 21: Ten (Or So) Great Organic Chemists 295 CHAPTER 22: Ten Cool Organic Discoveries 301 CHAPTER 23: Ten Cool Organic Molecules 307 Part 6: Appendixes 313 APPENDIX A: Working Multistep Synthesis Problems 315 APPENDIX B: Working Reaction Mechanisms 323 APPENDIX C: Glossary 329 Index 339

About the Author

Arthur Winter is a graduate of Frostburg State University, where he received his BS in chemistry. Arthur received his PhD at the University of Maryland in 2007, where his research involved studying extremely short-lived reactive intermediates.