Organic Chemistry I Workbook for Dummies

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