Organic Chemistry I Workbook for Dummies

Description

From models to molecules to mass spectrometry-solve organic chemistry problems with ease Got a grasp on the organic chemistry terms and concepts you need to know, but get lost halfway through a problem or worse yet, not know where to begin? Have no fear - this hands-on guide helps you solve the many types of organic chemistry problems you encounter in a focused, step-by-step manner. With memorization tricks, problem-solving shortcuts, and lots of hands-on practice exercises, you'll sharpen your skills and improve your performance. You'll see how to work with resonance; the triple-threat alkanes, alkenes, and alkynes; functional groups and their reactions; spectroscopy; and more! 100s of Problems! Know how to solve the most common organic chemistry problems Walk through the answers and clearly identify where you went wrong (or right) with each problem Get the inside scoop on acing your exams! Use organic chemistry in practical applications with confidence Organic Chemistry I Workbook for Dummies About the Author Dedication Author’s Acknowledgments Contents at a Glance Table of Contents Introduction About This Book Conventions Used in This Book Foolish Assumptions How This Book Is Organized Icons Used in This Book Where to Go from Here Part I: The Fundamentals of Organic Chemistry Chapter 1: Working with Models and Molecules Constructing Lewis Structures Predicting Bond Types Determining Bond Dipoles Determining Dipole Moments for Molecules Predicting Atom Hybridizations and Geometries Making Orbital Diagrams Answer Key Chapter 2: Speaking Organic Chemistry: Drawing and Abbreviating Lewis Structures Assigning Formal Charges Determining Lone Pairs on Atoms Abbreviating Lewis Structures with Condensed Structures Drawing Line-Bond Structures Determining Hydrogens on Line-Bond Structures Answer Key Chapter 3: Drawing Resonance Structures Seeing Cations Next to a Double Bond, Triple Bond, or Lone Pair Pushing Lone Pairs Next to a Double or Triple Bond Pushing Double or Triple Bonds Containing an Electronegative Atom Alternating Double Bonds around a Ring Drawing Multiple Resonance Structures Assigning Importance to Resonance Structures Answer Key Chapter 4: Working with Acids and Bases Defining Acids and Bases Comparing Acidities of Organic Molecules Predicting Acid-Base Equilibria Using pKa Values Answer Key Part II: The Bones of Organic Molecules: The Hydrocarbons Chapter 5: Seeing Molecules in 3-D: Stereochemistry Identifying Chiral Centers and Assigning Substituent Priorities Assigning R & S Configurations to Chiral Centers Working with Fischer Projections Comparing Relationships between Stereoisomers and Meso Compounds Answer Key Chapter 6: The Skeletons of Organic Molecules: The Alkanes Understanding How to Name Alkanes Drawing a Structure from a Name Answer Key Chapter 7: Shaping Up with Bond Calisthenics and Conformation Setting Your Sights on Newman Projections Comparing Conformational Stability Choosing Sides: The Cis-Trans Stereochemistry of Cycloalkanes Getting a Ringside Seat with Cyclohexane Chair Conformations Predicting Cyclohexane Chair Stabilities Answer Key Chapter 8: Doubling Down: The Alkenes Giving Alkenes a Good Name Markovnikov Mixers: Adding Hydrohalic Acids to Alkenes Adding Halogens and Hydrogen to Alkenes Just Add Water: Adding H2O to Alkenes Seeing Carbocation Rearrangements Answer Key Chapter 9: Tripling the Fun: Alkyne Reactions and Nomenclature Playing the Name Game with Alkynes Adding Hydrogen and Reducing Alkynes Adding Halogens and Hydrohalic Acids to Alkynes Adding Water to Alkynes Creating Alkynes Back to the Beginning: Working Multistep Synthesis Problems Answer Key Part III: Functional Groups and Their Reactions Chapter 10: The Leaving Group Boogie: Substitution and Elimination of Alkyl Halides The Replacements: Comparing SN1 and SN2 Reactions Kicking Out Leaving Groups with Elimination Reactions Putting It All Together: Substitution and Elimination Answer Key Chapter 11: Not as Thunk as You Drink I Am: The Alcohols Name Your Poison: Alcohol Nomenclature Beyond Homebrew: Making Alcohols Transforming Alcohols ( without Committing a Party Foul) Answer Key Chapter 12: Conjugated Dienes and the Diels-Alder Reaction Seeing 1,2-and 1,4-Addition Reactions to Conjugated Dienes Dienes and Their Lovers: Working Forward in the Diels-Alder Reaction Reverse Engineering: Working Backward in the Diels-Alder Reaction Answer Key Chapter 13: The Power of the Ring: Aromatic Compounds Determining Aromaticity, Anti-aromaticity, or Nonaromaticity of Rings Figuring Out a Ring System’s MO Diagram Dealing with Directors: Reactions of Aromatic Compounds Order! Tackling Multistep Synthesis of Polysubstituted Aromatic Compounds Answer Key Part IV: Detective Work: Spectroscopy and Spectrometry Chapter 14: Breaking Up (Isn’t Hard to Do): Mass Spectrometry Identifying Fragments in the Mass Spectrum Predicting a Structure Given a Mass Spectrum Answer Key Chapter 15: Cool Vibrations: IR Spectroscopy Distinguishing between Molecules Using IR Spectroscopy Identifying Functional Groups from an IR Spectrum Answer Key Chapter 16: Putting Molecules under the Magnet: NMR Spectroscopy Seeing Molecular Symmetry Working with Chemical Shifts, Integration, and Coupling Putting It All Together: Solving for Unknown Structures Using Spectroscopy Answer Key Part V: The Part of Tens Chapter 17: The Ten Commandments of Organic Chemistry Thou Shalt Work the Practice Problems before Reading the Answers Thou Shalt Memorize Only What Thou Must Thou Shalt Understand Thy Mechanisms Thou Shalt Sleep at Night and Not in Class Thou Shalt Read Ahead Before Class Thou Shalt Not Fall Behind Thou Shalt Know How Thou Learnest Best Thou Shalt Not Skip Class Thou Shalt Ask Questions Thou Shalt Keep a Positive Outlook Chapter 18: Ten Tips for Acing Orgo Exams Scan and Answer the Easy Questions First Read All of Every Question Set Aside Time Each Day to Study Form a Study Group Get Old Exams Make Your Answers Clear by Using Structures Don’t Try to Memorize Your Way Through Work a Lot of Problems Get Some Sleep the Night Before Recognize Red Herrings Index