Organic Chemistry I Workbook For Dummies

Need help with organic chemistry? Get extra practice with this workbook 

If you’re looking for a little extra help with organic chemistry than your Organic Chemistry I class offers, Organic Chemistry I Workbook For Dummies is exactly what you need! It lets you take the theories you’re learning (and maybe struggling with) in class and practice them in the same format you’ll find on class exams and other licensing exams, like the MCAT. It offers tips and tricks to memorize difficult concepts and shortcuts to solving problems.  

This reference guide and practice book explains the concepts of organic chemistry (such as functional groups, resonance, alkanes, and stereochemistry) in a concise, easy-to-understand format that helps you refine your skills. It also includes real practice with hundreds of exam questions to test your knowledge. 

• Walk through the answers and clearly identify where you went wrong (or right) with each problem 
• Get practical advice on acing your exams 
• Use organic chemistry in practical applications 

Organic Chemistry I Workbook For Dummies provides you with opportunities to review the material and practice solving problems based on the topics covered in a typical Organic Chemistry I course. With the help of this practical reference, you can face down your exam and pass on to Organic Chemistry II with confidence! 

Arthur Winter, PhD, is the author of the popular Organic Chemistry Help! website chemhelper.com and Organic Chemistry I For Dummies. His professional focus is on the chemistry of magneto-organic materials.

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 S_N1 and S_N2 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

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