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| Introduction | |
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| Bond-Line Drawings | |
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| How to Read Bond-Line Drawings | |
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| How to Draw Bond-Line Drawings | |
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| Mistakes to Avoid | |
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| More Exercises | |
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| Identifying Formal Charges | |
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| Finding Lone Pairs That Are Not Drawn | |
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| Resonance | |
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| What Is Resonance? | |
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| Curved Arrows: The Tools for Drawing Resonance Structures | |
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| The Two Commandments | |
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| Drawing Good Arrows | |
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| Formal Charges in Resonance Structures | |
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| Drawing Resonance Structures--Step by Step | |
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| Drawing Resonance Structures--By Recognizing Patterns | |
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| A Lone Pair Next to a Pi Bond | |
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| A Lone Pair Next to a Positive Charge | |
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| A Pi Bond Next to a Positive Charge | |
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| A Pi Bond Between Two Atoms, Where One of Those Atoms Is Electronegative (N, O, etc.) | |
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| Pi Bonds Going All the Way Around a Ring | |
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| Assessing the Relative Importance of Resonance Structures | |
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| Acid-Base Reactions | |
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| Factor 1--What Atom Is the Charge on? | |
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| Factor 2--Resonance | |
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| Factor 3--Induction | |
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| Factor 4--Orbitals | |
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| Ranking the Four Factors | |
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| Quantitative Measurement (pKa values) | |
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| Predicting the Position of Equilibrium | |
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| Showing a Mechanism | |
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| Geometry | |
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| Orbitals and Hybridization States | |
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| Geometry | |
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| Nomenclature | |
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| Functional Group | |
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| Unsaturation | |
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| Naming the Parent Chain | |
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| Naming Substituents | |
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| Stereoisomerism | |
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| Numbering | |
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| Common Names | |
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| Going from a Name to a Structure | |
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| Conformations | |
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| How to Draw a Newman Projection | |
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| Ranking the Stability of Newman Projections | |
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| Drawing Chair Conformations | |
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| Placing Groups on the Chair | |
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| Ring Flipping | |
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| Comparing the Stability of Chairs | |
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| Don't Be Confused by the Nomenclature | |
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| Configurations | |
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| Locating Stereocenters | |
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| Determining the Configuration of a Stereocenter | |
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| Nomenclature | |
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| Drawing Enantiomers | |
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| Diastereomers | |
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| Meso Compounds | |
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| Drawing Fischer Projections | |
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| Optical Activity | |
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| Mechanisms | |
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| Curved Arrows | |
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| Arro w Pushing | |
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| Drawing Intermediates | |
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| Nucleophiles and Electrophiles | |
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| Bases Versus Nucleophiles | |
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| The Regiochemistry Is Contained Within the Mechanism | |
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| The Stereochemistry Is Contained Within the Mechanism | |
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| A List of Mechanisms | |
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| Substitution Reactions | |
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| The Mechanisms | |
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| Factor 1--The Electrophile (Substrate) | |
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| Factor 2--The Nucleophile | |
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| Factor 3--The Leaving Group | |
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| Factor 4--The Solvent | |
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| Using All Four Factors | |
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| Substitution Reactions Teach Us Some Important Lessons | |
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| Elimination Reactions | |
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| Mechanisms (E1 and E2) | |
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| Factor 1--The Substrate | |
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| Factor 2--The Base | |
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| Factor 3--The Leaving Group | |
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| Factor 4--Solvent Effects | |
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| Using All of the Factors | |
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| Elimination Reactions--Regiochemistry and Stereochemistry | |
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| Addition Reactions | |
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| Terminology Describing Regiochemistry | |
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| Terminology Describing Stereochemistry | |
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| Adding H and H | |
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| Adding H and X, Markovnikov | |
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| Adding H and Br, Anti-Markovnikov | |
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| Adding H and OH, Markovnikov | |
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| Adding H and OH, Anti-Markovnikov | |
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| Synthesis Techniques | |
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| Adding Br and Br; Adding Br and OH | |
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| Adding OH and OH, Anti | |
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| Adding OH and OH, Syn | |
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| Oxidati ve Cleavage of an Alkene | |
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| Predicting Products | |
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| General Tips for Predicting Products | |
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| Getting Practice | |
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| Substitution Versus Elimination Reactions | |
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| Looking Forward | |
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| Synthesis | |
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| One-step Syntheses | |
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| Multistep Syntheses | |
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| Retrosynthetic Analysis | |
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| Creating Your Own Problems | |
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| Answer Key | |
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| Index | |