Brief Table of Contents Preface xxii CHAPTER 1 Remembering General Chemistry: Electronic Structure and Bonding 2 CHAPTER 2 Acids and bases Central to Understanding Organic Chemistry 50 TUTORIAL Acids and Bases 8o CHAPTER 3 An Introduction to organic compounds: Nomenclature,Physical Properties,and Structure 88 TUTORIAL Using Molecular Models 142 CHAPTER 4 Isomers:The Arrangement of Atoms in Space 143 TUTORIAL Interconverting Structural Representations 187 CHAPTER 5 Alkenes:Structure,Nomenclature,and an Introduction to Reactivity.Thermodynamics and Kinetics 190 TUTORIAL Drawing Curved Arrows 225 CHAPTER 6 The Reactions of Alkenes. The Stereochemistry of Addition Reactions 235 CHAPTER 7 The Reactions of Alkynes. An Introduction to Multistep Synthesis 288 CHAPTER 8 Delocalized Electrons:Their Effect on Stability,pKa,and the Products of a Reaction.Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene 318 TUTORIAL Drawing Resonance Contributors 382 CHAPTER 9 Substitution and Elimination Reactions of Alkyl Halides 391 CHAPTER 10 Reactions of Alcohols,Ethers,Epoxides,Amines,and Sulfur-Containing Compounds 458 CHAPTER 11 Organometallic Compounds 508 CHAPTER 12 Radicals 532 TUTORIAL Drawing Curved Arrows in Radical Systems 563 CHAPTER 13 Mass Spectrometry:Infrared Spectroscopy; UV/Vis Spectroscopy 567 CHAPTER 14 NMR Spectroscopy 620 CHAPTER 15 Reactions of Carboxylic Acids and Carboxylic Acid Derivatives 686 iv iv Brief Table of Contents Preface xxii CHAPTER 1 Remembering General Chemistry: Electronic Structure and Bonding 2 CHAPTER 2 Acids and Bases: Central to Understanding Organic Chemistry 50 TUTORIAL Acids and Bases 80 CHAPTER 3 An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure 88 TUTORIAL Using Molecular Models 142 CHAPTER 4 Isomers: The Arrangement of Atoms in Space 143 TUTORIAL Interconverting Structural Representations 187 CHAPTER 5 Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics 190 TUTORIAL Drawing Curved Arrows 225 CHAPTER 6 The Reactions of Alkenes • The Stereochemistry of Addition Reactions 235 CHAPTER 7 The Reactions of Alkynes • An Introduction to Multistep Synthesis 288 CHAPTER 8 Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene 318 TUTORIAL Drawing Resonance Contributors 382 CHAPTER 9 Substitution and Elimination Reactions of Alkyl Halides 391 CHAPTER 10 Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds 458 CHAPTER 11 Organometallic Compounds 508 CHAPTER 12 Radicals 532 TUTORIAL Drawing Curved Arrows in Radical Systems 563 CHAPTER 13 Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy 567 CHAPTER 14 NMR Spectroscopy 620 CHAPTER 15 Reactions of Carboxylic Acids and Carboxylic Acid Derivatives 686