Introduction 1
About This Book 1
Foolish Assumptions 2
Icons Used in This Book 3
Beyond the Book 3
Where to Go from Here 3
Part 1: The Fundamentals of Organic Chemistry 5
Chapter 1: Working with Models and Molecules 7
Constructing Lewis Structures 7
Predicting Bond Types 10
Determining Bond Dipoles 12
Determining Dipole Moments for Molecules 13
Predicting Atom Hybridizations and Geometries 15
Making Orbital Diagrams 17
Answer Key 20
Chapter 2: Speaking Organic Chemistry: Drawing and Abbreviating Lewis Structures 25
Assigning Formal Charges 26
Determining Lone Pairs on Atoms 29
Abbreviating Lewis Structures with Condensed Structures 30
Drawing Line-Bond Structures 33
Determining Hydrogens on Line-Bond Structures 36
Answer Key 38
Chapter 3: Drawing Resonance Structures 45
Seeing Cations Next to a Double Bond, Triple Bond, or Lone Pair 46
Pushing Lone Pairs Next to a Double or Triple Bond 49
Pushing Double or Triple Bonds Containing an Electronegative Atom 52
Alternating Double Bonds around a Ring 53
Drawing Multiple Resonance Structures 55
Assigning Importance to Resonance Structures 57
Answer Key 60
Chapter 4: Working with Acids and Bases 67
Defining Acids and Bases 68
Bronsted-Lowry acids and bases 68
Lewis acids and bases 70
Comparing Acidities of Organic Molecules 71
Contrasting atom electronegativity, size, and hybridization 71
The effect of nearby atoms 73
Resonance effects 75
Predicting Acid-Base Equilibria Using pKa Values 77
Answer Key 79
Part 2: The Bones of Organic Molecules: The Hydrocarbons 85
Chapter 5: Seeing Molecules in 3-D: Stereochemistry 87
Identifying Chiral Centers and Assigning Substituent Priorities 88
Assigning R & S Configurations to Chiral Centers 92
Working with Fischer Projections 95
Comparing Relationships between Stereoisomers and Meso Compounds 99
Answer Key 103
Chapter 6: The Skeletons of Organic Molecules: The Alkanes 113
Understanding How to Name Alkanes 114
Drawing a Structure from a Name 118
Answer Key 121
Chapter 7: Shaping Up with Bond Calisthenics and Conformation 127
Setting Your Sights on Newman Projections 128
Comparing Conformational Stability 131
Choosing Sides: The Cis-Trans Stereochemistry of Cycloalkanes 134
Getting a Ringside Seat with Cyclohexane Chair Conformations 135
Predicting Cyclohexane Chair Stabilities 137
Answer Key 140
Chapter 8: Doubling Down: The Alkenes 147
Giving Alkenes a Good Name 148
Markovnikov Mixers: Adding Hydrohalic Acids to Alkenes 152
Adding Halogens and Hydrogen to Alkenes 155
Just Add Water: Adding H2O to Alkenes 159
Seeing Carbocation Rearrangements 163
Answer Key 167
Chapter 9: Tripling the Fun: Alkyne Reactions and Nomenclature 179
Playing the Name Game with Alkynes 179
Adding Hydrogen and Reducing Alkynes 182
Adding Halogens and Hydrohalic Acids to Alkynes 185
Adding Water to Alkynes 189
Creating Alkynes 192
Back to the Beginning: Working Multistep Synthesis Problems 194
Answer Key 197
Part 3: Functional Groups and Their Reactions 205
Chapter 10: The Leaving Group Boogie: Substitution and Elimination of Alkyl Halides 207
The Replacements: Comparing SN1 and SN2 Reactions 208
Kicking Out Leaving Groups with Elimination Reactions 212
Putting It All Together: Substitution and Elimination 215
Answer Key 220
Chapter 11: Not as Thunk as You Drink I Am: The Alcohols 227
Name Your Poison: Alcohol Nomenclature 228
Beyond Homebrew: Making Alcohols 230
Transforming Alcohols (without Committing a Party Foul) 234
Answer Key 238
Chapter 12: Conjugated Dienes and the Diels-Alder Reaction 243
Seeing 1,2- and 1,4-Addition Reactions to Conjugated Dienes 244
Dienes and Their Lovers: Working Forward in the Diels-Alder Reaction 249
Reverse Engineering: Working Backward in the Diels-Alder Reaction 253
Answer Key 257
Chapter 13: The Power of the Ring: Aromatic Compounds 263
Determining Aromaticity, Anti-aromaticity, or Nonaromaticity of Rings 264
Figuring Out a Ring System’s MO Diagram 268
Dealing with Directors: Reactions of Aromatic Compounds 270
Order! Tackling Multistep Synthesis of Poysubstituted Aromatic Compounds 275
Answer Key 278
Part 4: Detective Work: Spectroscopy and Spectrometry 285
Chapter 14: Breaking Up (Isn’t Hard to Do): Mass Spectrometry 287
Identifying Fragments in the Mass Spectrum 287
Predicting a Structure Given a Mass Spectrum 296
Answer Key 300
Chapter 15: Cool Vibrations: IR Spectroscopy 303
Distinguishing between Molecules Using IR Spectroscopy 304
Identifying Functional Groups from an IR Spectrum 311
Answer Key 317
Chapter 16: Putting Molecules under the Magnet: NMR Spectroscopy 319
Seeing Molecular Symmetry 320
Working with Chemical Shifts, Integration, and Coupling 323
Putting It All Together: Solving for Unknown Structures Using Spectroscopy 328
Answer Key 340
Part 5: The Part of Tens 349
Chapter 17: The Ten Commandments of Organic Chemistry 351
Thou Shalt Work the Practice Problems before Reading the Answers 351
Thou Shalt Memorize Only What Thou Must 352
Thou Shalt Understand Thy Mechanisms 352
Thou Shalt Sleep at Night and Not in Class 353
Thou Shalt Read Ahead Before Class 353
Thou Shalt Not Fall Behind 353
Thou Shalt Know How Thou Learnest Best 354
Thou Shalt Not Skip Class 354
Thou Shalt Ask Questions 354
Thou Shalt Keep a Positive Outlook 354
Chapter 18: Ten Tips for Acing Orgo Exams 355
Scan and Answer the Easy Questions First 355
Read All of Every Question 356
Set Aside Time Each Day to Study 356
Form a Study Group 356
Get Old Exams 357
Make Your Answers Clear by Using Structures 357
Don’t Try to Memorize Your Way Through 357
Work a Lot of Problems 358
Get Some Sleep the Night Before 358
Recognize Red Herrings 358
Chapter 19: Ten Cool Natural Products 361
Maitotoxin 361
Penicillin 362
Nicotine 363
THC 363
Morphine 364
Taxol 364
Bombykol 365
The Green Fluorescent Protein Fluorophore 365
Ladderanes 366
Caffeine 366
Index 367
