Organic Chemistry I Workbook For Dummies

402 Pages·2022·15.39 MB·english

by  Arthur Winter

Organic
Chemistry I
Workbook
2nd Edition
by Arthur Winter, PhD
Organic Chemistry I Workbook For Dummies,® 2nd Edition
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Library of Congress Control Number: 2021950191
ISBN 978-1-119-85577-4 (pbk); ISBN 978-1-119-85578-1 (ebk); ISBN 978-1-119-85579-8 (ebk)
Contents at a Glance
Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1
Part 1: The Fundamentals of Organic Chemistry . . . . . . . . . . . . . . . . . . 5
CHAPTER 1: Working with Models and Molecules . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7
CHAPTER 2: Speaking Organic Chemistry: Drawing and Abbreviating Lewis Structures . . . . . . . . .25
CHAPTER 3: Drawing Resonance Structures . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 45
CHAPTER 4: Working with Acids and Bases . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 67
Part 2: The Bones of Organic Molecules: The Hydrocarbons . . . . . . . 85
CHAPTER 5: Seeing Molecules in 3-D: Stereochemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 87
CHAPTER 6: The Skeletons of Organic Molecules: The Alkanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 113
CHAPTER 7: Shaping Up with Bond Calisthenics and Conformation . . . . . . . . . . . . . . . . . . . . . . . . .127
CHAPTER 8: Doubling Down: The Alkenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 147
CHAPTER 9: Tripling the Fun: Alkyne Reactions and Nomenclature . . . . . . . . . . . . . . . . . . . . . . . . . 179
Part 3: Functional Groups and Their Reactions . . . . . . . . . . . . . . . . . . 205
CHAPTER 10: The Leaving Group Boogie: Substitution and Elimination of Alkyl Halides . . . . . . . . .207
CHAPTER 11: Not as Thunk as You Drink I Am: The Alcohols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 227
CHAPTER 12: Conjugated Dienes and the Diels-Alder Reaction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 243
CHAPTER 13: The Power of the Ring: Aromatic Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 263
Part 4: Detective Work: Spectroscopy and Spectrometry . . . . . . . . 285
CHAPTER 14: Breaking Up (Isn’t Hard to Do): Mass Spectrometry . . . . . . . . . . . . . . . . . . . . . . . . . . . . 287
CHAPTER 15: Cool Vibrations: IR Spectroscopy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 303
CHAPTER 16: Putting Molecules under the Magnet: NMR Spectroscopy . . . . . . . . . . . . . . . . . . . . . . 319
Part 5: The Part of Tens . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 349
CHAPTER 17: The Ten Commandments of Organic Chemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .351
CHAPTER 18: Ten Tips for Acing Orgo Exams . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 355
CHAPTER 19: Ten Cool Natural Products . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 361
Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 367

Table of Contents
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
Speaking Organic Chemistry: Drawing and
CHAPTER 2:
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
Table of Contents v
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 H O to Alkenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 159
2
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
The Leaving Group Boogie: Substitution and
CHAPTER 10:
Elimination of Alkyl Halides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .207
The Replacements: Comparing S 1 and S 2 Reactions . . . . . . . . . . . . . . . . . . . . . . . 208
N N
Kicking Out Leaving Groups with Elimination Reactions . . . . . . . . . . . . . . . . . . . . . . 212
Putting It All Together: Substitution and Elimination . . . . . . . . . . . . . . . . . . . . . . . . . 215
Answer Key . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 220
vi Organic Chemistry I Workbook For Dummies
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
Putting Molecules under the Magnet:
CHAPTER 16:
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
Table of Contents vii
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
viii Organic Chemistry I Workbook For Dummies