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What is included with this book?
Preface | p. vi |
Why do most Students Struggle with Organic Chemistry? | p. 1 |
Introduction | p. 1 |
How Organic Chemistry Is Different | p. 1 |
The Wrong Strategy | p. 2 |
The Right Strategy | p. 4 |
Organization and Goals of the Book | p. 6 |
Features of This Book | p. 7 |
Lewis dot Structures and the Chemical Bond | p. 9 |
Introduction | p. 11 |
Lewis Dot Structures | p. 11 |
Formal Charge | p. 16 |
Resonance | p. 20 |
Application: Drawing Lewis Structures of Complex Molecules Quickly | p. 25 |
Application: Draw All Resonance Contributors of... | p. 27 |
Application: Shorthand Notations | p. 36 |
What Did You Learn? | p. 41 |
Molecular Geometry, Dipole Moments, and Intermolecular Interactions | p. 44 |
Introduction | p. 46 |
VSEPR Theory and Three-Dimensional Molecular Geometry | p. 46 |
Tetrahedral Geometry and the Dash-Wedge Notation | p. 52 |
Rotations about Single and Double Bonds | p. 56 |
Bond Dipoles and Polarity | p. 58 |
Intermolecular Interactions | p. 64 |
Application: cis and trans Isomers | p. 76 |
Application: Melting Point and Boiling Point Determination | p. 78 |
Application: Solubility | p. 81 |
What Did You Learn? | p. 85 |
Isomerism | p. 88 |
Introduction | p. 90 |
Isomers: A Relationship | p. 90 |
Constitutional Isomerism | p. 91 |
Stereoisomerism: Enantiomers and Diastereomers | p. 95 |
Physical and Chemical Behavior of Isomers | p. 106 |
Application: Index of Hydrogen Deficiency (Degree of Unsaturation) | p. 108 |
Application: Draw All Constitutional Isomers of... | p. 112 |
Application: Draw All Stereoisomers of... | p. 116 |
What Did You Learn? | p. 120 |
Reaction Mechanisms 1: Elementary Steps | p. 122 |
Introduction | p. 124 |
Bond Formation (Coordination) and Bond Breaking (Heterolysis) | p. 125 |
Proton Transfers | p. 131 |
Bimolecular Nucleophilic Substitution (SN2) | p. 133 |
Nucleophilic Addition and Elimination | p. 134 |
Electrophilic Addition and Elimination | p. 137 |
Carbocation Rearrangements | p. 139 |
Bimolecular Elimination (E2) | p. 140 |
Application: Simplifying Assumptions about Electron-Rich and Electron-Poor Sites | p. 141 |
Application: Stereochemistry of Reactions and the Production of a New Stereocenter | p. 146 |
Application: Stereospecificity of SN2 Steps | p. 149 |
What Have You Learned? | p. 151 |
Charge Stability: Charge is Bad! | p. 156 |
Introduction | p. 158 |
Atomic Ions | p. 158 |
Molecular Ions | p. 161 |
Resonance Effects | p. 161 |
Inductive Effects | p. 163 |
Putting It All Together | p. 168 |
Application: Strengths of Acids and Bases | p. 170 |
Application: Strengths of Nucleophiles and the Hammond Postulate | p. 177 |
Application: Solvent Effects on Nucleophile Strength | p. 182 |
Application: The Best Resonance Contributor | p. 189 |
What Did You Learn? | p. 191 |
Reaction Mechanisms 2: SN1 and E1 Reactions and Rules of Thumb for Multistep Mechanisms | p. 193 |
Introduction | p. 195 |
Elementary Steps as Part of Multistep Mechanisms: SN1 and E1 Reactions | p. 195 |
Consequences of Single-Step Versus Multistep Mechanisms | p. 200 |
Proton Transfers as Part of Multistep Mechanisms | p. 204 |
Molecularity of Elementary Steps | p. 210 |
Application: Tautomerization Reactions-Neutral, Acidic, and Basic Conditions | p. 211 |
Application: Dealing with Relatively Lengthy Mechanisms-Fischer Esterification and Imine Formation | p. 215 |
What Did You Learn? | p. 220 |
SN1/SN2/E1/E2 Reactions: The Whole Story | p. 224 |
Introduction | p. 227 |
Rate-Determining Steps: Rate Laws and the Role of the Attacking Species | p. 228 |
Factor #1: Strength of Attacking Species | p. 232 |
Factor #2: Concentration of Nucleophile/Base | p. 233 |
Factor #3: Stability of the Leaving Group | p. 235 |
Factor #4: Type of Carbon Atom Bonded to the Leaving Group | p. 237 |
Factor #5: Solvent Effects | p. 240 |
Substitution Versus Elimination | p. 241 |
Sample Problems-Putting It All Together | p. 244 |
What Did You Learn? | p. 253 |
Concluding Remarks-What Now? | p. 256 |
Solutions to Selected End-of-Chapter Problems | p. 258 |
Index | p. 275 |
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