TABLE OF CONTENTS Preface... Symbols and Abbreviations. Introduction and Review. 1 Chapter 2 Structure and Properties of Organic Molecules 25 Chapter 3 Structure and Stereochemistry of Alkanes... .45 Chapter 4 The Study of Chemical Reactions...... 59 Chapter 5 Stereochemistry 70 Chapter 6 Alkyl Halides:Nucleophilic Substitution and Elimination.... .99 Chapter 7 Structure and Synthesis of Alkenes. 135 Chapter 8 Reactions of Alkenes............ ..159 Chapter 9 Alkynes........ 191 Chapter 10 Structure and Synthesis of Alcohols... .211 Chapter 11 Reactions of Alcohols 229 Chapter 12 Infrared Spectroscopy and Mass Spectrometry. 259 Chapter 13 Nuclear Magnetic Resonance Spectroscopy .271 Chapter 14 Ethers,Epoxides,and Sulfides... 299 Chapter 15 Conjugated Systems,Orbital Symmetry,and Ultraviolet Spectroscopy... .317 Chapter 16 Aromatic Compounds. 341 Chapter 17 Reactions of Aromatic Compounds... .365 Chapter 18 Ketones and Chapter 19 Amines. .439 Chapter 20 Carboxylic Acids..... 469 Chapter 21 Carboxylic Acid Derivatives... 499 Chapter 22 Condensations and Alpha Substitutions of Carbonyl Compounds Chapter 23 Carbohydrates and Nucleic Acids.... .585 Chapter24 Amino Acids,Peptides,and Proteins .617 Chapter 25 Lipids. 645 Chapter26 Synthetic Polymers. .659 Appendix 1:Summary of IUPAC Nomenclature.... ....675 Appendix 2:Summary of Acidity and Basicity 689 TABLE OF CONTENTS Preface ........................................................................................................................................ v Symbols and Abbreviations ...................................................................................................... vii Chapter 1 Chapter 2 Chapter 3 Chapter 4 Chapter 5 Chapter 6 Chapter 7 Chapter 8 Chapter 9 Chapter 10 Chapter 11 Chapter 12 Chapter 13 Chapter 14 Chapter 15 Chapter 16 Chapter 17 Chapter 18 Chapter 19 Chapter 20 Chapter 21 Chapter 22 Chapter 23 Chapter 24 Chapter 25 Chapter 26 Appendix I: Appendix 2: Introduction and Review ..... . ....... . ... . ................ . ....... ................. . .............. ............ 1 Structure and Properties of Organic Molecules .................................................. 25 Structure and Stereochemistry of Alkanes .................................... ...................... 45 The Study of Chemical Reactions . . . ...................... ............................................. 59 Stereochemistry .... . .............. . ...... ................................ . ........ . ............................. 79 Alkyl Halides: Nucleophilic Substitution and Elimination ................. . ....... ....... 99 Structure and Synthesis of Alkenes ... . ..... . ........ . . .............................................. 135 Reactions of Alkenes ... . ......... ... ....... . . .............................................................. 159 Alkynes ...... . . ........................ . .............................................. . ................. .......... 191 Structure and Synthesis of Alcohols .............. ....................... . .... . ...................... 211 Reactions of Alcohols .................. . ................................ ............ ............ ........... 229 Infrared Spectroscopy and Mass Spectrometry ........ . ............ ................ . ...... ..... 259 Nuclear Magnetic Resonance Spectroscopy ....... . . ............................ . .... . . ... ...... 271 Ethers, Epoxides, and Sulfides ................................. . .......... ............................. 299 Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy ............ 317 Aromatic Compounds ...... ................. . ........................... ................................... 341 Reactions of Aromatic Compounds ............................................ ......... . ............ 365 Ketones and Aldehydes .............. .... . ................. ............................. .................. 401 Amines .................. . .... ... ........... ....................................................................... 439 Carboxylic Acids ............................................................................................. 469 Carboxylic Acid Derivatives ...................................................... ...................... 499 Condensations and Alpha Substitutions of Carbonyl Compounds ... . ... . . ........... 537 Carbohydrates and Nucleic Acids ................................ . ........ ........ ................... 585 Amino Acids, Peptides, and Proteins ................................................... ............ 617 Lipids ... . ................................................... . ...................................................... 645 Synthetic Polymers . ... . ..... . . ............... . ........... .......... . ....... ................................. 659 Summary of IUPAC Nomenclature ... . ........ .......... . ................. .......... ................ 675 Summary of Acidity and Basicity ...... ........................... .................. . ... . ............ 689 iii