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| Introduction | |
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| About This Book | |
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| Conventions Used in This Book | |
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| Foolish Assumptions | |
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| How This Book Is Organized | |
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| Icons Used in This Book | |
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| Where to Go from Here | |
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| Going Organic: The Chemistry of Carbon | |
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| The Wonderful World of Organic Chemistry | |
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| Shaking Hands with Organic Chemistry | |
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| What Are Organic Molecules, Exactly? | |
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| An Organic Chemist by Any Other Name | |
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| Dissecting Atoms: Atomic Structure and Bonding | |
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| Electron House-Arrest: Shells and Orbitals | |
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| Atom Marriage: Bonding | |
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| To Share or Not to Share: Ionic and Covalent Bonding | |
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| Separating Charge: Dipole Moments | |
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| Seeing Molecular Geometries | |
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| It's All Greek to Me: Sigma and Pi Bonding | |
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| Speaking with Pictures: Drawing Structures | |
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| Picture-Talk: Lewis Structures | |
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| Problem Solving: Arrow Pushing | |
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| Drawing Resonance Structures | |
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| Covering the Bases (And the Acids) | |
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| A Defining Moment: Acid-Base Definitions | |
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| Comparing Acidities of Organic Molecules | |
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| Defining pKa: A Quantitative Scale of Acidity | |
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| Problem Solving: Predicting the Direction of Acid-Base Reactions at Equilibrium | |
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| Reactivity Centers: Functional Groups | |
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| Hydrocarbons | |
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| Singly Bonded Heteroatoms | |
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| Carbonyl Compounds | |
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| Test Your Knowledge | |
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| Seeing in 3-D: Stereochemistry | |
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| Drawing Molecules in 3-D | |
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| Comparing Stereoisomers and Constitutional Isomers | |
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| Mirror Image Molecules: Enantiomers | |
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| Seeing Chiral Centers | |
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| Assigning Configurations to Chiral Centers: The R/S Nomenclature | |
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| Problem Solving: Determining R/S Configuration | |
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| The Consequences of Symmetry: Meso Compounds | |
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| Rotating Plane-Polarized Light | |
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| Multiple Chiral Centers: Diastereomers | |
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| Representing 3-D Structures on Paper: Fischer Projections | |
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| Keeping the Jargon Straight | |
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| Hydrocarbons | |
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| The Bones of Organic Molecules: The Alkanes | |
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| What's in a Name? Alkane Nomenclature | |
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| Converting a Name to a Structure | |
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| Problem Solving: Drawing Isomers from a Molecular Formula | |
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| Conformation of Straight-Chain Alkanes | |
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| Full Circle: Cycloalkanes | |
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| Problem Solving: Drawing the Most Stable Chair Conformation | |
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| Reacting Alkanes: Free Radical Halogenation | |
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| Seeing Double: The Alkenes | |
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| Defining Alkenes | |
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| Taking Away Hydrogens: Degrees of Unsaturation | |
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| Nomenclature of alkenes | |
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| Stereochemistry of alkenes | |
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| Stabilities of Alkenes | |
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| Formation of Alkenes | |
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| Reactions of Alkenes | |
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| It Takes Alkynes: The Carbon-Carbon Triple Bond | |
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| Naming Alkynes | |
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| Seeing Alkyne Orbitals | |
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| Alkynes in Rings | |
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| Making Alkynes | |
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| Functional Groups | |
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| Replacing and Removing: Substitution and Elimination Reactions | |
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| Group Swap: Substitution Reactions | |
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| Seeing Second-Order Substitution: The S[subscript N]2 Mechanism | |
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| First-Order Substitution: The S[subscript N]1 Reaction | |
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| Seeing Elimination Reactions | |
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| Help! Distinguishing Substitution from Elimination | |
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| Getting Drunk on Organic Molecules: The Alcohols | |
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| Classifying Alcohols | |
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| An Alcohol By Any Other Name: Naming Alcohols | |
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| Alcohol-Making Reactions | |
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| Reactions of Alcohols | |
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| Side-By-Side: Conjugated Alkenes and the Diels-Alder Reaction | |
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| Seeing Conjugated Double Bonds | |
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| Addition of Hydrohalic Acids to Conjugated Alkenes | |
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| The Diels-Alder Reaction | |
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| Problem Solving: Determining Products of Diels-Alder Reaction | |
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| Lord of the Rings: Aromatic Compounds | |
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| Defining Aromatic Compounds | |
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| Explaining Aromaticity: Molecular Orbital Theory | |
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| Problem Solving: Determining Aromaticity | |
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| Problem Solving: Predicting Acidities and Basicities | |
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| Naming Benzenes and Aromatics | |
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| Bringing Out the Howitzers: Electrophilic Aromatic Substitution of Benzene | |
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| Adding Two: Synthesis of Disubstituted Benzenes | |
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| Problem Solving: Synthesis of Substituted Benzenes | |
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| Nucleophiles Attack! Nucleophilic Aromatic Substitution | |
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| Spectroscopy and Structure Determination | |
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| A Smashing Time: Mass Spectrometry | |
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| Defining Mass Spectrometry | |
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| Taking Apart a Mass Spectrometer | |
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| The Mass Spectrum | |
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| Kind and Caring: Sensitivity of Mass Spec | |
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| Resolving the Problem: Resolution | |
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| Changing the Weight: Isotopes | |
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| The Nitrogen Rule | |
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| Identifying Common Fragmentation Patterns | |
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| Key Ideas Checklist | |
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| Seeing Good Vibrations: IR Spectroscopy | |
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| Bond Calisthenics: Infrared Absorption | |
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| Dissecting an IR Spectrum | |
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| Identifying the Functional Groups | |
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| Seeing to the Left of the C-H Absorptions | |
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| Seeing to the Right of the C-H Absorptions | |
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| NMR Spectroscopy: Hold on to Your Hats, You're Going Nuclear! | |
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| Why NMR? | |
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| How NMR Works | |
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| The NMR Spectrum | |
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| The NMR Spectrum Manual: Dissecting the Pieces | |
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| Considering Carbon NMR | |
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| Checklist: Putting the Pieces Together | |
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| Following the Clues: Solving Problems in NMR | |
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| Follow the Clues | |
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| Working Problems | |
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| Three Common Mistakes in NMR Problem Solving | |
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| The Part of Tens | |
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| Ten Keys for Surviving Orgo | |
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| Have a Good Attitude | |
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| Work the Problems | |
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| Don't Fall Behind | |
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| Study the Right Way | |
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| Go to Class | |
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| Get Help When You Need It | |
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| Ask Questions | |
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| Do Organic Every Day | |
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| Take Exams the Right Way | |
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| Work the Problems | |
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| Ten Cool Organic Discoveries | |
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| Explosives and Dynamite! | |
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| Fermentation | |
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| The Synthesis of Urea | |
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| The Handedness of Tartaric Acid | |
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| Diels-Alder Reaction | |
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| Buckyballs | |
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| Soap | |
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| Aspartame | |
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| Peicillin | |
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| Teflon | |
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| Ten Great Organic Chemists | |
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| Robert Burns Woodward | |
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| August Kekule | |
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| K.C. Nicolaou | |
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| E.J. Corey | |
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| Louis Pasteur | |
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| Dorothy Hodgkin | |
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| Emil Fischer | |
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| Linus Pauling | |
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| John Pople | |
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| Friedrich Wohler and Adolf Kolbe | |
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| Appendixes | |
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| Working Multistep Synthesis Problems | |
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| Why Multistep Synthesis? | |
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| The Five Commandments | |
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| Working Reaction Mechanisms | |
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| The Two Unspoken Mechanism Types | |
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| Do's and Don'ts for Working Mechanisms | |
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| Types of Mechanisms | |
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| Seeing by Example: Example Mechanism Problem | |
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| Glossary | |
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| Index | |