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Introduction | |
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Important Concepts That Underlie Most of Organic Chemistry | |
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Electronegativity | |
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Ionic and Covalent Bonding | |
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Writing Chemical Structures | |
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Isomerism | |
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Resonance | |
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Hydrogen-Bonding and Boiling Points | |
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Water-Solubility | |
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Acid-Base Concepts | |
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Functional Groups | |
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Chapter 1 Review Problems | |
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Alkanes | |
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Structure and Bonding | |
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IUPAC Nomenclature | |
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Shapes of Simple Alkanes | |
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Shapes of Cyclic Alkanes | |
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Physical Properties of Alkanes | |
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Chapter 2 Review Problems | |
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Stereochemistry | |
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Stereogenic Atoms | |
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Naming Molecules with Stereogenic Atoms: The R,S (Cahn-Ingold-Prelog) System | |
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Possible Relationships Between Two Structures with the Same Molecular Formula | |
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Optical Rotation | |
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Implications of Stereoisomerism | |
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Chapter 3 Review Problems | |
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Alkenes | |
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Structure and Bonding | |
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IUPAC Nomenclature | |
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Physical Properties | |
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The General Reaction of Alkenes: Addition to the C=C | |
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Introduction to Reaction Mechanisms | |
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Addition Reactions of Alkenes, Classified by Mechanistic Similarities | |
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Diels-Alder Reaction | |
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Preparations of Alkenes | |
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Chapter 4 Review Problems | |
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Alkynes | |
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Structure and Bonding | |
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IUPAC Nomenclature | |
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The General Reaction of Alkynes: Addition to the C[identical with]C | |
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Additions of H-X and Water | |
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Addition of X[subscript 2] | |
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Hydroboration | |
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Oxidation of Alkynes with KMnO[subscript 4] and Ozone | |
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Reduction | |
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Acidity of 1-Alkynes | |
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Preparations of Alkynes | |
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Chapter 5 Review Problems | |
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Nucleophilic Substitution and Elimination Reactions | |
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Base Strength and Nucleophile Strength in Water and Hydrogen-Bonding Solvents | |
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Base Strength and Nucleophile Strength in Other Solvents | |
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Reactions of Methyl and Primary Alkyl Halides with Strong Nucleophiles/Bases | |
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Reactions of Tertiary Alkyl Halides with Strong Nucleophiles/Bases | |
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Reactions of Secondary Alkyl Halides with Strong Nucleophiles/Bases | |
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Reactions of Tertiary Alkyl Halides with Weak Nucleophiles/Bases | |
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Reactions of Secondary Alkyl Halides with Weak Nucleophiles/Bases | |
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Reactions of Methyl and Primary Alkyl Halides with Weak Nucleophiles/Bases | |
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Carbocation Rearrangements | |
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Summary of Nucleophilic Substitution and Elimination Reactions | |
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Chapter 6 Review Problems | |
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Free-Radical Reactions | |
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Introduction to Free-Radicals | |
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Free-Radical Chlorination of Methane | |
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The Energetics of Halogenation of Methane with Other Halogens | |
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Free-Radical Chlorination of Other Alkanes | |
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Free-Radical Bromination of Alkanes | |
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The Selectivity of Free-Radical Bromination Versus Chlorination | |
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Other Halogenating Agents | |
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Free-Radical Halogenation of Allylic and Benzylic Hydrogens | |
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Oxygen as a Free-Radical | |
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Chapter 7 Review Problems | |
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Alcohols and Thiols | |
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IUPAC Nomenclature of Alcohols | |
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Physical Properties of Alcohols | |
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Reactions That Cleave the O-H Bond | |
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Reactions That Cleave the C-O Bond | |
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Oxidation of Alcohols | |
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Preparations of Alcohols | |
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Thiol Naming and Properties | |
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Thiol Reactions and Preparations | |
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Chapter 8 Review Problems | |
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Ethers, Thioethers, and Epoxides | |
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Structure and Nomenclature | |
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Physical Properties | |
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Preparations | |
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Reactions | |
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Chapter 9 Review Problems | |
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Aromatic Compounds | |
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Structure of Benzene | |
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Unexpected Stability of Benzene | |
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Huckel's Rules | |
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Aromatic and Antiaromatic Compounds | |
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Nomenclature of Benzene Derivatives | |
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Electrophilic Aromatic Substitution of Benzene | |
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Electrophilic Aromatic Substitution of Substituted Benzenes: Directing Abilities | |
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Electrophilic Aromatic Substitution of Substituted Benzenes: Activating or Deactivating Effects | |
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Synthesis of Disubstituted and Trisubstituted Benzenes | |
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Phenol Naming and Properties | |
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Other Aromatic Compounds | |
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Chapter 10 Review Problems | |
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Amines | |
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Nomenclature | |
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Physical Properties | |
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Basicity | |
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Reactions as Nucleophiles | |
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Reactions of Amines with Nitrous Acid | |
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Preparations | |
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Chapter 11 Review Problems | |
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Aldehydes and Ketones | |
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Nomenclature | |
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Physical Properties | |
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General Reaction: Nucleophilic Addition to the C=O | |
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Reactions with Strong Nucleophiles | |
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Reactions with Weak Nucleophiles | |
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Oxidations of Aldehydes | |
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Reductions of Aldehydes and Ketones | |
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Preparations | |
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Acidity of the Alpha-Hydrogen | |
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Halogenation at the Alpha-Carbon | |
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Aldol Condensation | |
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Chapter 12 Review Problems | |
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Carboxylic Acids and Derivatives | |
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Structures | |
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Nomenclature of Carboxylic Acids | |
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Physical Properties of Carboxylic Acids | |
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Acidity of Carboxylic Acids | |
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The General Reaction of Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution, Addition-Elimination, or "Up, Down, and Out" | |
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Conversions of Carboxylic Acids into Carboxylic Acid Derivatives | |
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Acid Chlorides: Naming and Properties | |
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Anhydrides: Naming and Properties | |
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Esters: Naming and Properties | |
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Amides: Naming and Properties | |
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Nitriles: Naming and Properties | |
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Interconversions of Carboxylic Acids and Derivatives | |
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Reductions of Carboxylic Acids and Derivatives | |
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Chapter 13 Review Problems | |
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More Chemistry of Enols and Enolates | |
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Acidities of Various Types of C-H Bonds | |
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Alkylation of Malonic Esters and Acetoacetic Esters | |
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The Knoevenagel Condensation | |
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The Claisen Condensation and Related Reactions | |
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Conjugate Addition Reactions (The Michael Reaction) | |
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Robinson Annelation | |
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Alkylations and Acylations of Ketones | |
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Chapter 14 Review Problems | |
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Spectroscopy | |
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Infrared Spectroscopy | |
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Nuclear Magnetic Resonance Spectroscopy | |
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Mass Spectrometry | |
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Putting It All Together to Solve Problems | |
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Chapter 15 Review Problems | |
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Answers to Review Problems | |
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Final Exam | |
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Answers to Final Exam | |
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Index | |