Along the way, you see how to determine dipoles for bonds and for molecules — an extremely useful tool for predicting solubility and reactivity of organic molecules.Constructing Lewis St
Organic Chemistry I Workbook 2nd Edition by Arthur Winter, PhD Organic Chemistry I Workbook For Dummies,® 2nd Edition Published by: John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030-5774, www.wiley.com Copyright © 2022 by John Wiley & Sons, Inc., Hoboken, New Jersey Published simultaneously in Canada No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning or otherwise, except as permitted under Sections 107 or 108 of the 1976 United States Copyright Act, without the prior written permission of the Publisher Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, (201) 748-6011, fax (201) 748-6008, or online at http://www.wiley.com/go/permissions Trademarks: Wiley, For Dummies, the Dummies Man logo, Dummies.com, Making Everything Easier, and related trade dress are trademarks or registered trademarks of John Wiley & Sons, Inc and may not be used without written permission All other trademarks are the property of their respective owners John Wiley & Sons, Inc is not associated with any product or vendor mentioned in this book LIMIT OF LIABILITY/DISCLAIMER OF WARRANTY: WHILE THE PUBLISHER AND AUTHORS HAVE USED THEIR BEST EFFORTS IN PREPARING THIS WORK, THEY MAKE NO REPRESENTATIONS OR WARRANTIES WITH RESPECT TO THE ACCURACY OR COMPLETENESS OF THE CONTENTS OF THIS WORK AND SPECIFICALLY DISCLAIM ALL WARRANTIES, INCLUDING WITHOUT LIMITATION ANY IMPLIED WARRANTIES OF MERCHANTABILITY OR FITNESS FOR A PARTICULAR PURPOSE NO WARRANTY MAY BE CREATED OR EXTENDED BY SALES REPRESENTATIVES, WRITTEN SALES MATERIALS OR PROMOTIONAL STATEMENTS FOR THIS WORK THE FACT THAT AN ORGANIZATION, WEBSITE, OR PRODUCT IS REFERRED TO IN THIS WORK AS A CITATION AND/OR POTENTIAL SOURCE OF FURTHER INFORMATION DOES NOT MEAN THAT THE PUBLISHER AND AUTHORS ENDORSE THE 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print and electronic formats and by print-on-demand Some material included with standard print versions of this book may not be included in e-books or in print-on-demand If this book refers to media such as a CD or DVD that is not included in the version you purchased, you may download this material at http://booksupport.wiley.com For more information about Wiley products, visit www.wiley.com 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 Part 1: The Fundamentals of Organic Chemistry CHAPTER 1: CHAPTER 2: CHAPTER 3: CHAPTER 4: Working with Models and Molecules Speaking Organic Chemistry: Drawing and Abbreviating Lewis Structures �����������������25 Drawing Resonance Structures 45 Working with Acids and Bases 67 Part 2: The Bones of Organic Molecules: The Hydrocarbons CHAPTER 5: CHAPTER 6: CHAPTER 7: CHAPTER 8: CHAPTER 9: 85 Seeing Molecules in 3-D: Stereochemistry 87 The Skeletons of Organic Molecules: The Alkanes 113 Shaping Up with Bond Calisthenics and Conformation 127 Doubling Down: The Alkenes 147 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 Vibrations: IR Spectroscopy 303 CHAPTER 16: Putting Molecules under the Magnet: NMR Spectroscopy 319 CHAPTER 15: Cool 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 Cool Natural Products 361 CHAPTER 19: Ten Index 367 Table of Contents INTRODUCTION About This Book Foolish Assumptions Icons Used in This Book Beyond the Book Where to Go from Here PART 1: THE FUNDAMENTALS OF ORGANIC CHEMISTRY Working with Models and Molecules CHAPTER 1: Constructing Lewis Structures 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: CHAPTER 3: CHAPTER 4: Speaking Organic Chemistry: Drawing and Abbreviating Lewis Structures 25 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 26 29 30 33 36 38 Drawing Resonance Structures 45 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 46 49 52 53 55 57 60 Working with Acids and Bases 67 Defining Acids and Bases Bronsted-Lowry acids and bases Lewis acids and bases Comparing Acidities of Organic Molecules Contrasting atom electronegativity, size, and hybridization The effect of nearby atoms Resonance effects Predicting Acid-Base Equilibria Using pKa Values Answer Key 68 68 70 71 71 73 75 77 79 Table of Contents v PART 2: THE BONES OF ORGANIC MOLECULES: THE HYDROCARBONS 85 Seeing Molecules in 3-D: Stereochemistry 87 CHAPTER 5: 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: CHAPTER 8: Shaping Up with Bond Calisthenics and Conformation 127 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 128 131 134 135 137 140 Doubling Down: The Alkenes 147 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 148 152 155 159 163 167 Tripling the Fun: Alkyne Reactions and Nomenclature 179 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 179 182 185 189 192 194 197 PART 3: FUNCTIONAL GROUPS AND THEIR REACTIONS 205 CHAPTER 9: CHAPTER 10: vi The Leaving Group Boogie: Substitution and Elimination of Alkyl Halides 207 The Replacements: Comparing SN1 and SN2 Reactions Kicking Out Leaving Groups with Elimination Reactions Putting It All Together: Substitution and Elimination Answer Key 208 212 215 220 Organic Chemistry I Workbook For Dummies CHAPTER 11: CHAPTER 12: Not as Thunk as You Drink I Am: The Alcohols 227 Name Your Poison: Alcohol Nomenclature Beyond Homebrew: Making Alcohols Transforming Alcohols (without Committing a Party Foul) Answer Key 228 230 234 238 Conjugated Dienes and the Diels-Alder Reaction 243 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 244 249 253 257 The Power of the Ring: Aromatic Compounds 263 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 Poysubstituted Aromatic Compounds Answer Key 264 268 270 275 278 PART 4: DETECTIVE WORK: SPECTROSCOPY AND SPECTROMETRY 285 Breaking Up (Isn’t Hard to Do): Mass Spectrometry 287 CHAPTER 13: CHAPTER 14: 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 The Ten Commandments of Organic Chemistry 351 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 351 352 352 353 353 353 354 CHAPTER 17: Table of Contents vii Thou Shalt Not Skip Class 354 Thou Shalt Ask Questions 354 Thou Shalt Keep a Positive Outlook 354 CHAPTER 18: 355 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 355 356 356 356 357 357 357 358 358 358 Ten Cool Natural Products 361 Maitotoxin Penicillin Nicotine THC Morphine Taxol Bombykol The Green Fluorescent Protein Fluorophore Ladderanes Caffeine 361 362 363 363 364 364 365 365 366 366 INDEX 367 CHAPTER 19: viii Ten Tips for Acing Orgo Exams Organic Chemistry I Workbook For Dummies alkenes, 148 propylbenzene, 294–295, 302 alkynes, 180, 197–198 propyl substituent, 114, 122, 123 substituents, 114–115 proteins, 361 penicillin, 362 proton donor, 69 pentane purely covalent bond, 10, 21 Newman projection, 131, 133, 141, 142 pyridinium chlorochromate (PCC), 234, 234–236, 241 parent and substituent names, 114 staggered conformation, 133, 142 pentavalent bond, 50 pentavalent carbon, 64 1-penten-3-yne, 197 pentet, 344 pentyl substituent, 114 2-pentyne, 306–307 1-pentyne, 306–307 Q quartet, 341 quaternary carbons, 281 quinoline, 182 R R-3-methyl-2-butanol, 230, 238–239 peripheral atoms, racemic products, 223 Perkin, William, 263 R configurations, 89, 92–95, 96, 105–108 peroxides, 196 reaction coordinate diagram, 245 pi bonds, 17, 24 reactions pi electrons 1,2-addition, 244–248, 257–258 in benzene rings, 341 1,4-addition, 244–248, 257–258 Hückel number, 264 acid-base, 68–69, 69, 70–71, 71–76, 77–78, 79, 79–84, 83–84 in resonance structures, 46–48, 50, 52–53, 60 and ring aromaticity, 264–267, 278–280 pKa values, 77–78, 83–84 planar geometry, 212 plane of symmetry, 100–101, 110–111, 340 poisoned palladium catalyst, 182 polar covalent bond, 10, 21 positive outlook, 354 potassium amide, 11 potassium permanganate, 283 potassium tert-butoxide, 222 practice problems, working on, 351–352 primary alcohols, 231–236 primary amides, 318 primary amine, 317 primary carbocations, 152–153, 163–165, 220 propane lowest-energy conformation, 133 Newman projection, 130, 140 parent and substituent names, 114 2-propanol, 308, 317 propionic acid, 308, 317 propylamine, 309, 317 deprotonation, 212 Diels-Alder, 243, 249–253, 258–260 double dehydrohalogenation, 192 E1, 213, 223–224 E2, 212–219, 223–224 E2 reactions, 222–223 elimination, 212–214, 212–219, 221–223, 223–224 Grignard, 230–232, 241 halogenation, 155–159, 156, 172–175, 185–188, 199–200 hydroboration, 160, 161, 162 hydrogenation, 155–159, 156, 172–175, 182–184, 198 hydrohalic acid addition, 152–155, 171–172, 185–188, 199–200, 243 Markovnikov addition, 152–155, 159, 159–163, 171–172, 175–176, 189–191, 200–201 McLafferty rearrangement, 281, 289–292, 301 oxidation, 234–237, 241–242 oxymercuration/demercuration, 159, 161 polysubstituted, 275–277, 283–284 reduction, 182–184, 198, 230–231 reverse Diels-Alder, 253–255 Index 379 reactions (continued) SN1, 208–211, 215–219, 220–221, 223–224 SN2, 208–211, 215–219, 220–221, 223–224 Hückel number, 264 molecular orbital diagrams, 267–268, 279–280 nonaromaticity, 264–267, 278–280 substitution, 208–211, 215–219, 220–221, 223–224 syn addition, 156 trans addition, 156 water-addition, 189–191, 200–201 red herrings, 358–359 reduction reactions alkynes, 182–184, 198 carboxylic acids, 230–231 esters, 230–231 ketones, 230–231 relative ratios, 323–324, 340 replacements, 208–211, 220–221 resonance structures and acidity, 75–76, 82–83 answer key, 60–66 arrow pushing, 46–48, 60–61 assigning importance to, 57–59, 65–66 cations in, 46–47 defined, 45 double bonds, 49–51, 61–62 and electronegative atoms, 52–53, 62–63 and Lewis structures, 45 lone pairs, 49–51, 61–62 multiple, 55–57, 64–65 ring systems with alternating double bonds, 53–55, 63–64 rules, 46 retrosynthesis, 194 reverse Diels-Alder reaction adding double bonds to diene and dienophile, 254 breaking the bonds, 254 S scanning pattern-matching method, 39 S configurations, 92–95, 96, 105–108 secondary alcohols, 234–237 secondary amine, 317 secondary carbocations, 152–153, 163–165, 176, 220–221 secondary metabolites, 361 secondary substrates, 209 sex pheromone, 365 sextet, 341 Shimomura, Osamu, 365 sigma adduct, 282 sigma bonds, 17, 24 single bonds and chiral centers, 88–89, 104–105 defined, 17 and formal charges, 26–27, 38 in meso compounds, 100 in resonance structures, 45–67, 50 sigma bonds, 17 singlets, 341 size of atoms, 72 skipping classes, 354 sleep, 353, 358 SN1 reactions, 208–211, 215–219, 220–221, 223–224 SN2 reactions, 208–211, 215–219, 220–221, 223–224 sodium, 21 examples, 254–255 sodium borohydride (NaBH4), 159–163, 175–176, 230, 240 number of carbons, 254 sodium fluoride, 12 stereochemistry, 254 solid wedge, 127 using retrosynthesis in, 253 sp hybridization, 15–18, 22–24 right-most carbon sp2 hybridization, 15–17, 22–24 lone pairs, 50 sp3 hybridization, 15–17, 22–24 in multiple resonance structures, 56 spectroscopy, infrared (IR) ring flip, 136 absorbances, 304 ring structures distinguishing between molecules, 303–310 alternating double bonds, 53–55 functional groups, 305 alternative double bonds, 63–64 overview, 303 anti-aromaticity, 264–267, 278–280 spectrum, 304 aromaticity of, 264–267, 278–280 wavenumbers, 304 380 Organic Chemistry I Workbook For Dummies spectroscopy, nuclear magnetic resonance (NMR) structures, Lewis answer key, 340–347 adding valence electrons to the molecule, chemical equivalence in, 320 answer key, 38–43 chemically unique atoms, 320 condensed structures, 30–33 chemical shift, 323, 327, 341 connectivity of atoms, common fragments, 329 constructing, 7–10 coupling, 323 filling each atom’s octet, degrees of unsaturation, 328, 331, 342, 343, 344 formal charges, 26–28 deshielding, 323 line-bond structures, 33–35 diamagnetic anisotropy, 323, 342 lone pairs, 29–30 doublets, 323 number of valence electrons, integration curves, 323 orbital diagrams, 17–19 mirror planes, 320 molecular symmetry, 319–322 and resonance structures, 45 structures, line-bond, 41–43 multiplet, 344 carbon chain in, 33, 41 n + rule, 325, 327, 341 double bonds in, 41 overview, 320 drawing, 33–35 pentet, 344 four-membered ring, 35, 42 quartet, 341 hydrogens on, 36–37, 43 relative ratios, 323–324, 340 nitrogen in, 34 sextet, 341 singlets, 341 triple bonds in, 41 structures, resonance solving for unknown structures, 328–339 and acidity, 75–76, 82–83 sum of relative ratios, 324 answer key, 60–66 triplets, 323, 341 arrow pushing, 46–48, 60–61 staggered conformation, 129 assigning importance to, 57–59, 65–66 stereochemistry cations in, 46–47 alcohol, 228, 238–239 defined, 45 answer key, 103–111 double bonds, 49–51, 61–62 Cahn-Ingold-Prelog rules, 88–89 and electronegative atoms, 52–53, 62–63 chiral centers, 88–91 and Lewis structures, 45 cis stereochemistry, 148 lone pairs, 49–51, 61–62 defined, 87 multiple, 55–57, 64–65 Diels-Alder reaction, 249–250 ring systems with alternating double bonds, 53–55, 63–64 E stereochemistry, 149 Fischer projections, 95–99, 108–110 meso compounds, 99–102, 110–111 plane of symmetry, 100–101 R and S configurations, 92–95, 96, 105–108 stereoisomers, 99–102, 110–111 trans stereochemistry, 148 Z stereochemistry, 149 stereoisomers, 87, 99–102, 110–111 steric strain, 260 rules, 46 structures, ring alternating double bonds, 53–55 alternative double bonds, 63–64 anti-aromaticity, 264–267, 278–280 aromaticity of, 264–267, 278–280 Hückel number, 264 molecular orbital diagrams, 267–268, 279–280 nonaromaticity, 264–267, 278–280 Index 381 study groups, 356–357 substituents ten commandments of organic chemistry asking questions, 354 alcohol, 228, 238–239 getting enough sleep, 353 alkanes, 114–115 knowing how you learn the best, 354 alkenes, 148–149 memorization, 352 alkynes, 180 not falling behind, 353 butyl, 114, 117 not skipping class, 354 t-butyl, 122 positive outlook, 354 and chiral centers, 103–104 reading ahead before class, 353 chlorine, 150, 180 understanding the mechanisms, 352 cyclobutyl, 123, 183 work the problems before reading the answers, 351–352 cyclopropyl, 115 decyl, 114 defined, 114 ethyl, 114, 116 fluorine, 150, 180 heptyl, 114 hexyl, 114 iodine, 180 ten cool natural products bombykol, 365 caffeine, 366 green fluorescent protein, 365 ladderanes, 366 maitotoxin, 361–362 morphine, 364 isopropyl, 119, 142 nicotine, 363 methyl, 114, 116, 119, 121, 122, 123, 197 taxol, 364 nenyl, 114 penicillin, 362 tetrahydrocannabinol, 363 octyl, 114 terminal alkynes, 192–193 pentyl, 114 tert-butoxide, 211, 222 priorities, assigning, 88–89, 103–104 tert-butylcyclohexane, 117, 122 propyl, 114, 122, 123 tertiary alcohols, 234–237 substitution reactions, 208–211, 215–219, 220–221, 223–224 tertiary butyl chloride, 342 substrates, 209, 212–214, 213, 220 tertiary carbocations, 152–153, 163–165, 176–177, 220–221 sulfonation, 271 tetrahalides, 185 sulfur, 81 tetrahydrocannabinol (THC), 363 sulfuric acid, 200 thermodynamic products, 245 syn addition, 156, 160 thiols, 209 synthesis 3-D models alcohols, 239–241 answer key, 103–111 alkynes, 194–196, 203 Cahn-Ingold-Prelog rules, 88–89 aromatic compounds, 275–277, 283–284 chiral centers, 88–91 retrosynthesis, 194 defined, 87 Fischer projections, 95–99, 108–110 T meso compounds, 99–102, 110–111 tautomerization, 189–191, 200–201 taxol, 364 382 Organic Chemistry I Workbook For Dummies plane of symmetry, 100–101 R and S configurations, 92–95, 96, 105–108 stereoisomers, 99–102, 110–111 tips for acing exams, 355 hydrogenation reactions, 182–184, 198 forming study groups, 356–357 hydrohalic acid addition reactions, 185–188, 199–200 getting enough sleep, 358 IR absorption, 305, 305–307 getting old exams, 357 in line-bond structures, 41 making answers clear by using structures, 357 and lone pairs, 49–51, 61–62 memorization, 357 reduction reactions, 182–184, 198 reading every questions, 356 resonance structures, 46–48, 60–61 recognizing red herrings, 358–359 scanning and answering the easy questions first, 355–356 setting aside time each day to study, 356 work a lot of problems, 358 totally eclipsed conformation, 132 trans-1,2-dibromocyclohexane, 138 trans-1,2-dichloroethane, 14, 21 trans-1,2-dimethylcyclohexane, 145–146 trans-1,4-diethylcyclohexane, 138, 144 trans-1-chloro-2-methylcylohexane, 135, 142 trans-5-methyl-2-hexene, 149 trans addition, 156 trans-alkenes, 182, 183, 198 trans configuration, 134–135 trans products, 156 trans stereochemistry, 148 triple bonds arrow pushing, 52–53, 62–63, 185–186 Cahn-Ingold-Prelog rules, 88–89, 104–105 cations next to, 46–48, 60–61 electronegativity, 52–53, 62–63 water-addition reactions, 189–191, 200–201 triplets, 323, 341 Tsien, Roger, 365 V valence electrons, 8–9, 20, 26 W water acidity, 73 addition to alkenes, 159–163, 175–176 addition to alkynes, 189–191 wavenumbers, 304 Williamson ether synthesis, 235–236, 242 Wohler, Friedrich, 351 working on problems, 351–352, 358 Z Z-1-chloro-1-fluoro-1-pentene, 146, 150 Z stereochemistry, 149 halogenation reactions, 185–188, 199–200 Index 383 About the Author Arthur Winter received his BS in chemistry from Frostburg State University, his PhD in chemistry from the University of Maryland, and did a postdoctoral fellowship at Ohio State University He currently is a professor of chemistry at Iowa State University He is the author of Organic Chemistry I For Dummies (Wiley) His two major research interests involve exploiting photochemistry to solve challenging problems in medicine and using high-powered lasers to start small laboratory fires Dedication For Julie Winter Author’s Acknowledgments I thank the good folks at Wiley for making this workbook possible First, I thank Lindsay Lefevere and Kathy Cox for getting the ball rolling on this project and keeping it on a steady course I also thank Chad Sievers, Danielle Voirol, and Alissa Schwipps for their dedication and patience with the editing the first edition, and Greg Tubach, Michelle Hacker, and Katharine Dvorak for help with this new edition Publisher’s Acknowledgments Senior Acquisitions Editor: Greg Tubach Production Editor: Mohammed Zafar Ali Managing Editor: Michelle Hacker Cover Image: © Sebastian Duda/Shutterstock Project Editor: Katharine Dvorak Technical Editor: Joe C. Burnell, PhD Take dummies with you everywhere you go! 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