TABLE OF CONTENTS Preface Symbols and Abbreviations Introduction and Review.... Chapter 2 Structure and Properties of Organic Molecules3 Chapter3 Structure and Stereochemistry of Alkanes... 52 Chapter 4 The Study of Chemical Reactions......... .68 Chapter 5 Stereochemistry....... 87 Chapter6 Alkyl Halides:Nucleophilic Substitution and Elimination.. 106 Chapter 7 Structare and Synthesis of Alkenes141 Chapter8 Reactions of Alkenes. .167 Chapter 9 Alkynes....... 198 Chapter10 Structure and Synthesis of Alcohols .216 Reactions of Alcohols.. 235 Chapter 12 Infrared Spectroscopy and Mass Spectrometry......................................... 264 Chapter 13 Nuclear Magnetic Resonance Spectroscopy 277 Chapter 14 Ethers,Epoxides,and Thioethers......... 306 Chapter 15 Conjugated Systems,Orbital Symmetry,and Ultraviolet Spectroscopy .326 Aromatic Compounds… .346 Chapter 17 Reactions of Aromatic Compounds 371 Chapter18 Ketones and Aldehydes. .405 Chapter 19 Amines.. 4144444444444* .439 Chapter 20 Carboxylic Acids .467 Chapter 21 Carboxylic Acid Derivatives.. 496 Chapter 22 Condensations and Alpha Substitutions of Carbonyl Compounds 531 Chapter23 Carbohydrates and Nucleic Acids. 58 Chapter24 Amino Acids,Peptides,and Proteins.... 613 Chapter 25 .641 Chapter 26 Synthetic Polymers. .657 Appendix 1:Summary of IUPAC Nomenclature of Organie Compounds 675 Appendix 2:Summary of Acidity and Basicity..... 689 Appendix 3:Sample Alkene Reaction Summary.. 701 iii