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| Note: Each chapter concludes with Additional Problems | |
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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 | |
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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 A Closer Look at...Natural Gas | |
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| Sources of Alkanes | |
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| Physical Properties of Alkanes and Nonbonding Intermolecular Interactions | |
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| 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-transIsomerism in Cycloalkanes | |
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| A Word About: Isomers- Possible and Impossible | |
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| Summary of Isomerism | |
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| Reactions of Alkanes | |
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| A Word About: Methane, Marsh Gas, and Miller's Experiment | |
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| The Free-Radical Chain Mechanism of Halogenation | |
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| Reaction Summary | |
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| Mechanism Summary | |
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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-transIsomerism in Alkenes | |
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| 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 | |
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| 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 Bonds | |
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| Additon Reactions of Alkynes | |
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| A Word About: Petroleum, Gasoline, and Octane Number | |
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| Acidity of Alkynes | |
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| Reaction Summary | |
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| Mechanism Summary | |
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| Aromatic Compounds | |
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| Some Facts About Benzene | |
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| The Kekuleacute; 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, andMeta-Directing Groups | |
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| The Importance of Directing Effects in Synthesis | |
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| Polycyclic Aromatic Hydrocarbons | |
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| A Word About: Polycyclic Aromatic Hydrocarbons and Cancer | |
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| A Closer Look at...Polycyclic Aromatic Hydrocarbons | |
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| A Word About: C60, an Aromatic Sphere: The Fullerenes | |
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| Reaction Summary | |
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| Mechanism Summary | |
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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 theR-SConvention | |
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| TheE-ZConvention forCis-transIsomers | |
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| Polarized Light and Optical Activity | |
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| 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 | |