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| Bonding and Isomerism | |
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| How Electrons Are Arranged in Atoms | |
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| Ionic and Covalent Bonding | |
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| Carbon and the Covalent Bond | |
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| Carbon-Carbon Single Bonds | |
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| Polar Covalent Bonds | |
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| Multiple Covalent Bonds | |
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| Valence | |
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| Isomerism | |
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| Writing Structural Formulas | |
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| Abbreviated Structural Formulas | |
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| Formal Charge | |
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| Resonance | |
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| Arrow Formalism | |
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| The Orbital View of Bonding; the Sigma Bond | |
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| Carbon sp3 Hybrid Orbitals | |
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| Tetrahedral Carbon; the Bonding in Methane | |
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| Classification According to Molecular Framework | |
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| Classification According to Functional Group Additional Problems | |
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| Alkanes and Cycloalkanes: Conformational and Geometric Isomerism | |
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| The Structures of Alkanes | |
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| Nomenclature of Organic Compounds | |
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| IUPAC Rules for Naming Alkanes | |
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| Alkyl and Halogen Substituents | |
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| Use of the IUPAC Rules | |
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| Sources of Alkanes A Closer Look At: Natural Gas | |
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| Physical Properties of Alkanes and Nonbonding Intermolecular Interactions A Closer Look At: Hydrogen Bonding | |
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| Conformations of Alkanes | |
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| Cycloalkane Nomenclature and Conformation | |
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| Cis-trans Isomerism in Cycloalkanes | |
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| Summary of Isomerism A Word About: Isomers, Possible and Impossible | |
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| Reactions of Alkanes A Word About: Methane, Marsh Gas, and Miller's Experiment | |
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| The Free-Radical Chain Mechanism of Halogenation Reaction Summary Mechanism Summary Additional Problems | |
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| Alkenes and Alkynes | |
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| Definition and Classification | |
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| Nomenclature | |
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| Some Facts About Double Bonds | |
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| The Orbital Model of a Double Bond; the Pi Bond | |
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| Cis-trans Isomerism in Alkenes A Word About: The Chemistry of Vision | |
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| Addition and Substitution Reactions Compared | |
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| Polar Addition Reactions | |
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| Addition of Unsymmetric Reagents to Unsymmetric Alkenes; Markovnikov's Rule | |
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| Mechanism of Electrophilic Addition to Alkenes | |
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| Markovnikov's Rule Explained | |
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| Reaction Equilibrium: What Makes a Reaction Go? | |
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| Reaction Rates: How Fast Does a Reaction Go? | |
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| Hydroboration of Alkenes | |
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| Addition of Hydrogen | |
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| Additions to Conjugated Systems | |
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| Free-Radical Additions; Polyethylene | |
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| Oxidation of Alkenes A Word About: Ethylene: Raw Material and Plant Hormone | |
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| Some Facts About Triple Bonds | |
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| The Orbital Model of a Triple Bond | |
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| Additon Reactions of Alkynes A Word About: Petroleum, Gasoline, and Octane Number A Closer Look At: Petroleum | |
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| Acidity of Alkynes Reaction Summary Mechanism Summary Additional Problems | |
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| Aromatic Compounds | |
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| Some Facts About Benzene | |
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| The Kekulea Structure of Benzene | |
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| The Resonance Model for Benzene | |
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| Orbital Model for Benzene | |
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| Symbols for Benzene | |
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| Nomenclature of Aromatic Compounds | |
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| The Resonance Energy of Benzene | |
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| Electrophilic Aromatic Substitution | |
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| The Mechanism of Electrophilic Aromatic Substitution | |
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| Ring-Activating and Ring-Deactivating Substituents | |
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| Ortho, Para-Directing, and Meta-Directing Groups | |
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| The Importance of Directing Effects in Synthesis | |
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| Polycyclic Aromatic Hydrocarbons A Word About: Polycyclic Aromatic Hydrocarbons and Cancer A Word About: C60, an Aromatic Sphere: The Fullerenes A Closer Look At: Polycyclic Aromatic Hydrocarbons Reaction Summary Mechanism Summary Additional Problems | |
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| Stereoisomerism | |
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| Chirality and Enantiomers | |
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| Stereogenic Centers; the Stereogenic Carbon Atom | |
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| Configuration and the R-S Convention | |
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| The E-Z Convention for Cis-trans Isomers | |
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| Polarized Light and Optical Activity A Word About: Pasteur's Experiments and the van't Hoff-LeBel Explanation | |
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| Properties of Enantiomers | |
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| Fischer Projection Formulas | |
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| Compounds with More Than One Stereogenic Center; Diastereomers | |
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| Meso Compounds; the Stereoisomers of Tartaric Acid | |
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| Stereochemistry; a Recap of Definitions | |
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| Stereochemistry and Chemical Reactions A Word About: Enantiomers and Biological Activity | |
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| Resolution of a Racemic Mixture A Closer Look At: Thalidomide Additional Problems | |
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| Organic Halogen Compounds; Substitution and Elimination Reactions | |
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| Nucleophilic Substitution | |
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| Examples of Nucleophilic Substitution | |
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| Nucleophilic Substitution Mechanism | |
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| The SN2 Mechanism | |
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| The SN1 Mechanism | |
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| The SN1 and SN2 Mechanisms Compared A Word About: SN2 Reactions in Nature: Biological Methylations | |
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| Dehydrohalogenation, an Elimination Reaction; the E2 and E1 Mechanisms | |
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| Substitution and Elimination in Competition | |
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| Polyhalogenated Aliphatic Compounds A Word About: CFCs, the Ozone Layer, and Trade-Offs A Word About: Halogenated Organic Compounds from the Sea Reaction Summary Mechanism Summary Additional Problems | |
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| Alcohols, Phenols, and Thiols | |
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| Nomenclature of Alcohols A Word About: Industrial Alcohols | |
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| Classification of Alcohols | |
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| Nomenclature of Phenols | |
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| Hydrogen Bonding in Alcohols and Phenols | |
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| Acidity and Basicity Reviewed | |
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| The Acidity of Alcohols and Phenols | |
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| The Basicity of Alcohols and Phenols | |
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| Dehydration of Alcohols to Alkenes | |
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| The Reaction of Alcohols with Hydrogen Halides | |
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| Other Ways to Prepare Alkyl Halides from Alcohols | |
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| A Comparison of Alcohols and Phenols | |
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| Oxidation of Alcohols to Aldehydes, Ketones, and Carboxylic Acids A Word About: Biologically Important Alcohols and Phenols | |
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| Alcohols with More Than One Hydroxyl Group | |
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| Aromatic Substitution in Phenols A Word About: Quinones and the Bombardier Beetle | |
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| Oxidation of Phenols | |
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| Phenols as Antioxidants | |
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| Thiols, the Sulfur Analogs of Alcohols and Phenols A Word About: Hair, Curly or Straight Reaction Summary Additional Problems | |
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| Ethers and Epoxides | |
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| Nomenclature of Ethers | |
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| Physical Properties of Ethers | |
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| Ethers as Solvents | |
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| The Grignard Reagent; an Organometallic Compound | |
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| Preparation of Ethers A Closer Look At: MTBE | |
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| Cleavage of Ethers A Word About: Ether and Anesthesia | |
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| Epoxides (Oxiranes) A Word About: The Gypsy Moth's Epoxide | |
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| Reactions of Epoxides | |
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| Cyclic Ethers Reaction Summary Additional Problems | |
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| Aldehydes and Ketones | |
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| Nomenclature of Aldehydes and Ketones | |
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| Some Common Aldehydes and Ketones | |
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| Synthesis of Aldehydes and Ketones | |
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| Aldehydes and Ketones in Nature | |
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| The Carbonyl Group | |
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| Nucleophilic Addition to Carbonyl Groups; an Overview | |
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| Addition of Alcohols: Formation of Hemiacetals and Acetals | |
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| Addition of Water; Hydration of Aldehydes and Ketones | |
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| Addition of Grignard Reagents and Acetylides | |
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| Addition of Hydrogen Cyanide; Cyanohydrins | |
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| Addition of Nitrogen Nucleophiles | |
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| Reduction of Carbonyl Compounds | |
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| Oxidation of Carbonyl Compounds | |
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| Keto-Enol Tautomerism | |
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| Acidity of a-Hydrogens; the Enolate Anion | |
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| Deuterium Exchanges in Carbonyl Compounds | |
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| The Aldol Condensation | |
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| The Mixed Aldol Condensation A Word About: Water Treatment and the Chemistry of Enols/Enolates | |
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| Commercial Syntheses via the Aldol Condensation Reaction Summary Mechanism Summary Additional Problems | |
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| Carboxylic Acids and Their Derivatives | |
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| Nomenclature of Acids | |
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| Physical Properties of Acids | |
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| Acidity and Acidity Constants | |
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| What Makes Carboxylic Acids Acidic? | |
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| Effect of Structure on Acidity; the Inductive Effect Revisited | |
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| Conversion of Acids to Salts | |
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| Preparation o | |