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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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