Organic Chemistry I Workbook For Dummies

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