Introduction Brief History of Organic Chemistry Variety and Beauty of Organic Molecules Notes Why Is an Acid-Base Theme Important? Acids and Bases in General Chemistry Acids and Bases in Organic Chemistry There Are Two Acid-Base Definitions: How Are They Related? Acid and Base Strength Electronegativity and Atom Size Determination of Acid-Base Strength Based on Electronegativity and Size Arguments Lewis Acids and Bases Why Is Acid-Base Chemistry a Theme for Organic Chemistry? Biological Relevance Correlation of Concepts with Homework Answers to In-Chapter Questions Homework Notes Bonding Orbitals and the Periodic Table Ionic versus Covalent Chemical Bonds Covalent Bonds Strength of a Covalent Bond Molecular Orbitals Tetrahedral Carbons and sp3Hybridization Breaking Covalent Bonds Polarized Covalent σ-Bonds Biological Relevance Correlation of Homework with Concepts Answers to In-Chapter Questions Homework Notes Alkanes, Isomers, and an Introduction to Nomenclature Fundamental Structure of Alkanes Based on the sp3-Hybrid Model Millions of Alkane Hydrocarbons Acid or Base Properties of Alkanes Naming Millions of Isomers: Rules of Nomenclature: The IUPAC Rules of Nomenclature Rings Made of Carbon: Cyclic Compounds Combustion Analysis and Empirical Formulas Biological Relevance Correlation of Homework with Concepts Answers to In-Chapter Questions Homework Notes Functional Groups Introducing a Functional Group: Alkenes Acid-Base Properties of Alkenes Hydrocarbon Functional Groups: Alkynes Hydrocarbons with Several π-Bonds Heteroatoms and Polarized Covalent σ-Bonds Formal Charge Reactive Intermediates Heteroatom Functional Groups Acid-Base Properties of Functional Groups Physical Properties and Intermolecular Forces Functional Groups with Polarized π-Bonds Benzene: A Special Cyclic Hydrocarbon Biological Relevance Correlation of Homework with Concepts Answers to In-Chapter Questions Homework Notes Acids, Bases, Nucleophiles, and Electrophiles Acid-Base Equilibria Factors That Influence Ka Factors That Influence the Strength of a Carboxylic Acid Energetics and Reaction Curves Alcohols and Amines Are Acids Hydrogen Atom Attached to a Carbon Is an Acid Acid-Base Reaction of Alkenes with Mineral Acids Lewis Acids and Bases Organic Bases Nucleophiles Biological Relevance Correlation of Homework with Concepts Answers to In-Chapter Questions Homework Notes Chemical Reactions, Bond Energy, and Kinetics Chemical Reaction Free Energy: Influence of Enthalpy and Entropy Bond-Dissociation Enthalpy and Reactions Transition States Energetics: Starting Materials, Transition States, Intermediaries, and Products on a Reaction Curve Competing Reactions Reaction Curves and Intermediaries Mechanisms Why Does a Chemical Reaction Occur? Defining a "Reactive" Center Reversible Chemical Reactions Kinetics No Reaction Biological Relevance Correlation of Homework with Concepts Answers to In-Chapter Questions Homework Notes Rotamers and Conformation Rotamers Longer Chain Alkanes Conformations of Alkenes and Alkynes: Introducing π-Bonds Influence of Heteroatoms on the Rotamer Population Cyclic Alkanes Substituted Cyclohexanes Larger Rings Cyclic Alkenes Introducing Heteroatoms into a Ring Biological Relevance Correlation of Homework with Concepts Answers to In-Chapter Questions Homework Notes Stereoisomers: Chirality, Enantiomers, and Diastereomers Stereogenic Carbons and Stereoisomers Absolute Configuration [( R ) and ( S ) Nomenclature] Specific Rotation: A Physical Property Relationship of Specific Rotation and Absolute Configuration Mixtures of Enantiomers and Racemates Alkenes Diastereomers Stereogenic Centers in Cyclic Molecules Stereogenic Centers in Complex Molecules Optical Resolution Biological Relevance Correlation of Homework with Concepts Answers to In-Chapter Questions Homework Notes Acid-Base Reactions of π-Bonds: Addition Reactions Alkenes and Acid-Base Chemistry Carbocation Intermediates Alkenes React with Weak Acids in the Presence of an Acid Catalyst Alkenes React as Lewis Bases with Dihalogens Alkenes React as Lewis Bases with Borane Alkenes React as Lewis Bases with Mercury(II) Compounds Alkynes React as Brønsted-Lowry Bases or Lewis Bases Oxidation Reactions of Alkenes Nonionic Reactions: Radicals and Alkene Polymerization Synthetic Transformations Organization of Reaction Types Biological Relevance Correlation of Homework with Concepts Answers to In-Chapter Questions Homework Notes Nucleophiles: Lewis Base-Like Reactions at sp3Carbon Alkyl Halides, Sulfonate Esters, and the Electrophilic C-X Bond Nucleophiles and Bimolecular Substitution (the SN2 Reaction) Functional Group Transformations via the SN2 Reaction Tertiary Halide Reacts with a Nucleophile When the Solvent Is Water Solvolysis Reactions of Alkyl Halides Preparation of Halides by Substitution Reactions Reactions of Ethers Free Radical Halogenation of Alkanes Synthetic Transformations Organization of Reaction Types Biological Relevance Correlation of Homework with Concepts Answers to In-Chapter Questions Homework Notes Bases-Induced Elimination Reactions Bimolecular Elimination Stereochemical Consequences of the E2 Reaction E2 Reaction in Cyclic Molecules Unimolecular Elimination: The E1 Reaction Intramolecular Elimination 1,3-Elimination: Decarboxylation Elimination Reactions of Vinyl Halides: Formation of Alkynes Functional Group Exchanges Based on Elimination Organization of Reaction Types Biological Relevance Correlation of Homework with Concepts Answers to In-Chapter Questions Homework Notes Substitution and Elimination Reactions Can Compete Few Simplifying Assumptions Protic versus Aprotic and Water Nucleophilic Strength versus Base Strength Nature of the Halide What about Secondary Halides? Strength and Limitations of the Simplifying Assumptions When Do the Assumptions Fail? Correlation of Homework with Concepts Answers to In-Chapter Questions Homework Notes Spectroscopic Methods of Identification Light and Energy Mass Spectrometry Infrared Spectroscopy Nuclear Magnetic Resonance Spectroscopy Identifying Monofunctional Molecules Carbon-13 NMR Spectroscopy: Counting the Carbons Biological Relevance Correlation of Homework with Concepts Answers to In-Chapter Questions Homework Notes Organic Molecules That Contain Alkali Metals or Transition Metals (Organometallics) Introducing Magnesium into a Molecule Reaction of Aryl and Vinyl Halides with Magnesium Grignard Reagents Are Bases Grignard Reagents Are Poor Nucleophiles with Alkyl Halides Organolithium Reagents Organocuprates Organometallic Disconnections Organization of Reaction Types Biological Relevance Correlation of Homework with Concepts Answers to In-Chapter Questions Homework Notes Carbonyl Compounds: Structure, Nomenclature, Reactivity Carbonyl Group Aldehydes and Ketones: Nomenclature Chemical Reactivity of Ketones and Aldehydes Carboxylic Acids: Nomenclature and Properties Dicarboxylic Acids Dicarboxylic Acids Have Two p Ka Values Carboxylic Acid Derivatives: Structure and Nomenclature Acyl Substitution with Carboxylic Acid Derivatives Sulfonic Acids Biological Relevance Correlation of Homework with Concepts Answers to In-Chapter Questions Homework Notes Oxidation Defining and Oxidation Oxidation of Alcohols with Chromium (VI) Oxidation of Alkenes Revisited Oxidative Cleavage Summary of Functional Group Exchanges Organization of Reaction Types Biological Relevance Correlation of Homework with Concepts Answers to In-Chapter Questions Homework Notes Reactions of Aldehydes and Ketones Chemical Reactivity of the Carbonyl Group Reaction of Aldehydes or Ketones with Strong Nucleophiles Weak Nucleophiles: Reversible versus Irreversible Acyl Addition Alcohols: Weak Nucleophiles That Yield Reactive Products Amines Are Nucleophiles Carbon-Carbon Bond-Forming Reactions and Functional Group Modification Organization of Reaction Types Biological Relevance Correlation of Homework with Concepts Answers to In-Chapter Questions Homework Notes Reduction Defining a Reduction Hydrides as Reducing Agents Hydride Reduction of Other Functional Groups Catalytic Hydrogenation Dissolving Metal Reductions Summary of Functiona.