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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 | |