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Copyright, iv
Introduction, v
Contents, ix
Chapter 1. BOND-LINE DRAWINGS, 1
1.1. How to Read Bond-Line Drawings, 1
1.2. How to Draw Bond-Line Drawings, 5
1.3. Mistakes to Avoid, 7
1.4. More Exercises, 8
1.5. Identifying Formal Charges, 10
1.6. Finding Lone Pairs That Are Not Drawn, 14
Chapter 2. RESONANCE, 20
2.1. What Is Resonance?, 20
2.2. Curved Arrows: The Tools for Drawing Resonance Structures, 21
2.3. The Two Commandments, 24
2.4. Drawing Good Arrows, 27
2.5. Formal Charges in Resonance Structures, 29
2.6. Drawing Resonance Structures—Step by Step, 33
2.7. Drawing Resonance Structures—By Recognizing Patterns, 38
A Lone Pair Next to a Pi Bond, 38
A Lone Pair Next to a Positive Charge, 41
A Pi Bond Next to a Positive Charge, 43
A Pi Bond Between Two Atoms, Where One of Those Atoms Is Electronegative (N, O, etc.), 44
Pi Bonds Going All the Way Around a Ring, 45
2.8. Assessing the Relative Importance of Resonance Structures, 47
Chapter 3. ACID–BASE REACTIONS, 53
3.1. Factor 1—What Atom Is the Charge on?, 54
3.2. Factor 2—Resonance, 57
3.3. Factor 3—Induction, 62
3.4. Factor 4—Orbitals, 66
3.5. Ranking the Four Factors, 67
3.6. Quantitative Measurement (pKa values), 71
3.7. Predicting the Position of Equilibrium, 71
3.8. Showing a Mechanism, 73
Chapter 4. GEOMETRY, 76
4.1. Orbitals and Hybridization States, 76
4.2. Geometry, 80
Chapter 5. NOMENCLATURE, 84
5.1. Functional Group, 85
5.2. Unsaturation, 87
5.3. Naming the Parent Chain, 89
5.4. Naming Substituents, 91
5.5. Stereoisomerism, 95
5.6. Numbering, 98
5.7. Common Names, 103
5.8. Going from a Name to a Structure, 104
Chapter 6. CONFORMATIONS, 106
6.1. How to Draw a Newman Projection, 107
6.2. Ranking the Stability of Newman Projections, 111
6.3. Drawing Chair Conformations, 115
6.4. Placing Groups on the Chair, 118
6.5. Ring Flipping, 123
6.6. Comparing the Stability of Chairs, 129
6.7. Don’t Be Confused by the Nomenclature, 133
Chapter 7. CONFIGURATIONS, 134
7.1. Locating Stereocenters, 135
7.2. Determining the Configuration of a Stereocenter, 138
7.3. Nomenclature, 146
7.4. Drawing Enantiomers, 151
7.5. Diastereomers, 156
7.6. Meso Compounds, 157
7.7. Drawing Fischer Projections, 160
7.8. Optical Activity, 165
Chapter 8. MECHANISMS, 167
8.1. Curved Arrows, 168
8.2. Arrow Pushing, 173
8.3. Drawing Intermediates, 175
8.4. Nucleophiles and Electrophiles, 178
8.5. Bases Versus Nucleophiles, 179
8.6. The Regiochemistry Is Contained Within the Mechanism, 182
8.7. The Stereochemistry Is Contained Within the Mechanism, 185
8.8. A List of Mechanisms, 190
Chapter 9. SUBSTITUTION REACTIONS, 211
9.1. The Mechanisms, 211
9.2. Factor 1—The Electrophile (Substrate), 214
9.3. Factor 2—The Nucleophile, 217
9.4. Factor 3—The Leaving Group, 220
9.5. Factor 4—The Solvent, 223
9.6. Using All Four Factors, 226
9.7. Substitution Reactions Teach Us Some Important Lessons, 227
Chapter 10. ELIMINATION REACTIONS, 229
10.1. Mechanisms (E1 and E2), 230
10.2. Factor 1—The Substrate, 231
10.3. Factor 2—The Base, 232
10.4. Factor 3—The Leaving Group, 235
10.5. Factor 4—Solvent Effects, 236
10.6. Using All of the Factors, 236
10.7. Elimination Reactions—Regiochemistry and Stereochemistry, 238
Chapter 11. ADDITION REACTIONS, 242
11.1. Terminology Describing Regiochemistry, 242
11.2. Terminology Describing Stereochemistry, 244
11.3. Adding H and H, 253
11.4. Adding H and X, Markovnikov, 256
11.5. Adding H and Br, Anti-Markovnikov, 263
11.6. Adding H and OH, Markovnikov, 268
11.7. Adding H and OH, Anti-Markovnikov, 272
11.8. Synthesis Techniques, 277
11.9. Adding Br and Br; Adding Br and OH, 285
11.10. Adding OH and OH, Anti, 290
11.11. Adding OH and OH, Syn, 293
11.12. Oxidative Cleavage of an Alkene, 296
Chapter 12. PREDICTING PRODUCTS, 299
12.1. General Tips for Predicting Products, 299
12.2. Getting Practice, 300
12.3. Substitution Versus Elimination Reactions, 311
12.4. Looking Forward, 315
Chapter 13. SYNTHESIS, 316
13.1. One-step Syntheses, 318
13.2. Multistep Syntheses, 329
13.3. Retrosynthetic Analysis, 330
13.4. Creating Your Own Problems, 331
Answer Key, 333
Index, 355

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