Organic Chemistry I Workbook For Dummies
von: Arthur Winter
For Dummies, 2009
ISBN: 9780470405246
Sprache: Englisch
363 Seiten, Download: 17085 KB
Format: PDF, auch als Online-Lesen
Title Page | 5 | ||
Copyright Page | 6 | ||
Table of Contents | 13 | ||
Introduction | 17 | ||
About This Book | 17 | ||
Conventions Used in This Book | 18 | ||
Foolish Assumptions | 18 | ||
How This Book Is Organized | 18 | ||
Part I: The Fundamentals of Organic Chemistry | 18 | ||
Part II: The Bones of Organic Molecules: Hydrocarbons | 19 | ||
Part III: Functional Groups and Their Reactions | 19 | ||
Part IV: Detective Work: Spectroscopy and Spectrometry | 19 | ||
Part V: The Part of Tens | 19 | ||
Icons Used in This Book | 20 | ||
Where to Go from Here | 20 | ||
Part 1 The Fundamentals of Organic Chemistry | 21 | ||
Chapter 1 Working with Models and Molecules | 23 | ||
Constructing Lewis Structures | 23 | ||
Predicting Bond Types | 26 | ||
Determining Bond Dipoles | 27 | ||
Determining Dipole Moments for Molecules | 28 | ||
Predicting Atom Hybridizations and Geometries | 30 | ||
Making Orbital Diagrams | 31 | ||
Answer Key | 34 | ||
Chapter 2 Speaking Organic Chemistry: Drawing and Abbreviating Lewis Structures | 39 | ||
Assigning Formal Charges | 39 | ||
Determining Lone Pairs on Atoms | 41 | ||
Abbreviating Lewis Structures with Condensed Structures | 42 | ||
Drawing Line-Bond Structures | 45 | ||
Determining Hydrogen son Line-Bond Structures | 47 | ||
Answer Key | 49 | ||
Chapter 3 Drawing Resonance Structures | 55 | ||
Seeing Cations Next to a Double Bond, Triple Bond, or Lone Pair | 56 | ||
Pushing Lone Pairs Next to a Double or Triple Bond | 59 | ||
Pushing Double or Triple Bonds Containing an Electronegative Atom | 61 | ||
Alternating Double Bonds around a Ring | 63 | ||
Drawing Multiple Resonance Structures | 65 | ||
Assigning Importance to Resonance Structures | 67 | ||
Answer Key | 69 | ||
Chapter 4 Working with Acids and Bases | 75 | ||
Defining Acids and Bases | 75 | ||
Bronsted-Lowry acids and bases | 76 | ||
Lewis acids and bases | 78 | ||
Comparing Acidities of Organic Molecules | 79 | ||
Contrasting atom electronegativity, size, and hybridization | 79 | ||
The effect of nearby atoms | 82 | ||
Resonance effects | 83 | ||
Predicting Acid-Base Equilibria Using pKa Values | 85 | ||
Answer Key | 87 | ||
Part 2 The Bones of Organic Molecules:The Hydrocarbons | 93 | ||
Chapter 5 Seeing Molecules in 3-D: Stereochemistry | 95 | ||
Identifying Chiral Centers and Assigning Substituent Priorities | 95 | ||
Assigning R & S Configurations to Chiral Centers | 99 | ||
Working with Fischer Projections | 102 | ||
Comparing Relationships between Stereoisomers and Meso Compounds | 105 | ||
Answer Key | 108 | ||
Chapter 6 The Skeletons of Organic Molecules: The Alkanes | 117 | ||
Understanding How to Name Alkanes | 117 | ||
Drawing a Structure from a Name | 122 | ||
Answer Key | 125 | ||
Chapter 7 Shaping Up with Bond Calisthenics and Conformation | 131 | ||
Setting Your Sights on Newman Projections | 131 | ||
Comparing Conformational Stability | 135 | ||
Choosing Sides: The Cis-Trans Stereochemistry of Cycloalkanes | 137 | ||
Getting a Ringside Seat with Cyclohexane Chair Conformations | 139 | ||
Predicting Cyclohexane Chair Stabilities | 141 | ||
Answer Key | 143 | ||
Chapter 8 Doubling Down: The Alkenes | 151 | ||
Giving Alkenes a Good Name | 151 | ||
Markovnikov Mixers: Adding Hydrohalic Acids to Alkenes | 156 | ||
Adding Halogens and Hydrogen to Alkenes | 159 | ||
Just Add Water: Adding H2O to Alkenes | 163 | ||
Seeing Carbocation Rearrangements | 167 | ||
Answer Key | 170 | ||
Chapter 9 Tripling the Fun: Alkyne Reactions and Nomenclature | 181 | ||
Playing the Name Game with Alkynes | 181 | ||
Adding Hydrogen and Reducing Alkynes | 184 | ||
Adding Halogens and Hydrohalic Acids to Alkynes | 186 | ||
Adding Water to Alkynes | 188 | ||
Creating Alkynes | 191 | ||
Back to the Beginning: Working Multistep Synthesis Problems | 194 | ||
Answer Key | 196 | ||
Part 3 Functional Groups and Their Reactions | 203 | ||
Chapter 10 The Leaving Group Boogie: Substitution and Elimination of Alkyl Halides | 205 | ||
The Replacements: Comparing SN1 and SN2 Reactions | 205 | ||
Kicking Out Leaving Groups with Elimination Reactions | 210 | ||
Putting It All Together: Substitution and Elimination | 213 | ||
Answer Key | 217 | ||
Chapter 11 Not as Thunk as You Drink I Am: The Alcohols | 223 | ||
Name Your Poison: Alcohol Nomenclature | 223 | ||
Beyond Homebrew: Making Alcohols | 226 | ||
Transforming Alcohols (without Committing a Party Foul) | 231 | ||
Answer Key | 234 | ||
Chapter 12 Conjugated Dienes and the Diels-Alder Reaction | 239 | ||
Seeing 1,2- and 1,4-Addition Reactions to Conjugated Dienes | 239 | ||
Dienes and Their Lovers: Working Forward in the Diels-Alder Reaction | 244 | ||
Reverse Engineering: Working Backward in the Diels-Alder Reaction | 249 | ||
Answer Key | 252 | ||
Chapter 13 The Power of the Ring: Aromatic Compounds | 257 | ||
Determining Aromaticity, Anti-aromaticity, or Nonaromaticity of Rings | 258 | ||
Figuring Out a Ring System’s MO Diagram | 261 | ||
Dealing with Directors: Reactions of Aromatic Compounds | 263 | ||
Order! Tackling Multistep Synthesis of Polysubstituted Aromatic Compounds | 267 | ||
Answer Key | 270 | ||
Part 4 Detective Work:Spectroscopy and Spectrometry | 277 | ||
Chapter 14 Breaking Up (Isn’t Hard to Do): Mass Spectrometry | 279 | ||
Identifying Fragments in the Mass Spectrum | 279 | ||
Predicting a Structure Given a Mass Spectrum | 287 | ||
Answer Key | 290 | ||
Chapter 15 Cool Vibrations: IR Spectroscopy | 293 | ||
Distinguishing between Molecules Using IR Spectroscopy | 293 | ||
Identifying Functional Groups from an IR Spectrum | 300 | ||
Answer Key | 306 | ||
Chapter 16 Putting Molecules under the Magnet: NMR Spectroscopy | 309 | ||
Seeing Molecular Symmetry | 309 | ||
Working with Chemical Shifts, Integration, and Coupling | 312 | ||
Putting It All Together: Solving for Unknown Structures Using Spectroscopy | 316 | ||
Answer Key | 327 | ||
Part 5 The Part of Tens | 335 | ||
Chapter 17 The Ten Commandments of Organic Chemistry | 337 | ||
Thou Shalt Work the Practice Problems before Reading the Answers | 337 | ||
Thou Shalt Memorize Only What Thou Must | 338 | ||
Thou Shalt Understand Thy Mechanisms | 338 | ||
Thou Shalt Sleep at Night and Not in Class | 338 | ||
Thou Shalt Read Ahead Before Class | 339 | ||
Thou Shalt Not Fall Behind | 339 | ||
Thou Shalt Know How Thou Learnest Best | 339 | ||
Thou Shalt Not Skip Class | 340 | ||
Thou Shalt Ask Questions | 340 | ||
Thou Shalt Keep a Positive Outlook | 340 | ||
Chapter 18 Ten Tips for Acing Orgo Exams | 341 | ||
Scan and Answer the Easy Questions First | 341 | ||
Read All of Every Question | 341 | ||
Set Aside Time Each Day to Study | 342 | ||
Form a Study Group | 342 | ||
Get Old Exams | 342 | ||
Make Your Answers Clear by Using Structures | 343 | ||
Don’t Try to Memorize Your Way Through | 343 | ||
Work a Lot of Problems | 343 | ||
Get Some Sleep the Night Before | 343 | ||
Recognize Red Herrings | 344 | ||
EULA | 363 |