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| Preface | |
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| Why do most Students Struggle with Organic Chemistry? | |
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| Introduction | |
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| How Organic Chemistry Is Different | |
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| The Wrong Strategy | |
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| The Right Strategy | |
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| Organization and Goals of the Book | |
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| Features of This Book | |
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| Lewis dot Structures and the Chemical Bond | |
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| Introduction | |
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| Lewis Dot Structures | |
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| Formal Charge | |
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| Resonance | |
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| Application: Drawing Lewis Structures of Complex Molecules Quickly | |
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| Application: Draw All Resonance Contributors of... | |
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| Application: Shorthand Notations | |
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| What Did You Learn? | |
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| Molecular Geometry, Dipole Moments, and Intermolecular Interactions | |
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| Introduction | |
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| VSEPR Theory and Three-Dimensional Molecular Geometry | |
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| Tetrahedral Geometry and the Dash-Wedge Notation | |
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| Rotations about Single and Double Bonds | |
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| Bond Dipoles and Polarity | |
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| Intermolecular Interactions | |
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| Application: cis and trans Isomers | |
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| Application: Melting Point and Boiling Point Determination | |
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| Application: Solubility | |
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| What Did You Learn? | |
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| Isomerism | |
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| Introduction | |
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| Isomers: A Relationship | |
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| Constitutional Isomerism | |
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| Stereoisomerism: Enantiomers and Diastereomers | |
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| Physical and Chemical Behavior of Isomers | |
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| Application: Index of Hydrogen Deficiency (Degree of Unsaturation) | |
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| Application: Draw All Constitutional Isomers of... | |
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| Application: Draw All Stereoisomers of... | |
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| What Did You Learn? | |
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| Reaction Mechanisms 1: Elementary Steps | |
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| Introduction | |
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| Bond Formation (Coordination) and Bond Breaking (Heterolysis) | |
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| Proton Transfers | |
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| Bimolecular Nucleophilic Substitution (SN2) | |
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| Nucleophilic Addition and Elimination | |
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| Electrophilic Addition and Elimination | |
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| Carbocation Rearrangements | |
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| Bimolecular Elimination (E2) | |
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| Application: Simplifying Assumptions about Electron-Rich and Electron-Poor Sites | |
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| Application: Stereochemistry of Reactions and the Production of a New Stereocenter | |
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| Application: Stereospecificity of SN2 Steps | |
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| What Have You Learned? | |
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| Charge Stability: Charge is Bad! | |
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| Introduction | |
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| Atomic Ions | |
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| Molecular Ions | |
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| Resonance Effects | |
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| Inductive Effects | |
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| Putting It All Together | |
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| Application: Strengths of Acids and Bases | |
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| Application: Strengths of Nucleophiles and the Hammond Postulate | |
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| Application: Solvent Effects on Nucleophile Strength | |
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| Application: The Best Resonance Contributor | |
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| What Did You Learn? | |
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| Reaction Mechanisms 2: SN1 and E1 Reactions and Rules of Thumb for Multistep Mechanisms | |
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| Introduction | |
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| Elementary Steps as Part of Multistep Mechanisms: SN1 and E1 Reactions | |
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| Consequences of Single-Step Versus Multistep Mechanisms | |
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| Proton Transfers as Part of Multistep Mechanisms | |
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| Molecularity of Elementary Steps | |
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| Application: Tautomerization Reactions-Neutral, Acidic, and Basic Conditions | |
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| Application: Dealing with Relatively Lengthy Mechanisms-Fischer Esterification and Imine Formation | |
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| What Did You Learn? | |
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| SN1/SN2/E1/E2 Reactions: The Whole Story | |
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| Introduction | |
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| Rate-Determining Steps: Rate Laws and the Role of the Attacking Species | |
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| Factor #1: Strength of Attacking Species | |
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| Factor #2: Concentration of Nucleophile/Base | |
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| Factor #3: Stability of the Leaving Group | |
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| Factor #4: Type of Carbon Atom Bonded to the Leaving Group | |
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| Factor #5: Solvent Effects | |
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| Substitution Versus Elimination | |
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| Sample Problems-Putting It All Together | |
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| What Did You Learn? | |
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| Concluding Remarks-What Now? | |
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| Solutions to Selected End-of-Chapter Problems | |
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| Index | |