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fourth editionORGANIC CHEMISTRYFrancis A. CareyUniversity of VirginiaBoston Burr Ridge, IL Dubuque, IA Madison, WI New York San Francisco St. LouisBangkok Bogotá Caracas Lisbon London MadridMexico City Milan New Delhi Seoul Singapore Sydney Taipei Toronto| | | |▲▲e-Text Main MenuTextbook Table of ContentsStudy Guide Table of ContentsORGANIC CHEMISTRY, FOURTH EDITIONCopyright © 2000, 1996, 1992, 1987 by The McGraw-Hill Companies, Inc. All rights reserved. Printed in theUnited States of America. Except as permitted under the United States Copyright Act of 1976, no part of thispublication may be reproduced or distributed in any form or by any means, or stored in a data base or retrievalsystem, without the prior written permission of the publisher.This book is printed on acid-free paper.1 2 3 4 5 7 8 9 0 VNH/VNH 9 0 9 8 7 6 5 4 3 2 1 0 9ISBN 0-07-290501-8Vice president and editorial director: Kevin T. KanePublisher: James M. SmithSponsoring editor: Kent A. PetersonDevelopmental editor: Terrance StantonEditorial assistant: Jennifer BensinkSenior marketing manager: Martin J. LangeSenior marketing assistant: Tami PetscheSenior project manager: Peggy J. SelleSenior production supervisor: Sandra HahnDesigner: K. Wayne HarmsPhoto research coordinator: John C. LelandSenior supplement coordinator: David A. WelshCompositor: GTS Graphics, Inc.Typeface: 10/12 Times RomanPrinter: Von Hoffmann Press, Inc.Cover/interior designer: Jamie O’NealPhoto research: Mary Reeg Photo ResearchThe credits section for this book begins on page C-1 and is considered an extension of the copyright page.Library of Congress Cataloging-in-Publication DataCarey, Francis A.Organic chemistry / Francis A. Carey. — 4th ed.p. cm.Includes index.ISBN 0-07-290501-8 — ISBN 0-07-117499-0 (ISE)1. Chemistry, Organic. I. Title.QD251.2.C364 2000547—dc21 99-045791CIPINTERNATIONAL EDITION ISBN 0-07-117499-0Copyright © 2000. Exclusive rights by The McGraw-Hill Companies, Inc. for manufacture and export. Thisbook cannot be re-exported from the country to which it is consigned by McGraw-Hill. The InternationalEdition is not available in North America.www. mhhe.comMcGraw-Hill Higher EducationA Division of The McGraw-Hill Companies| | | |▲▲e-Text Main MenuTextbook Table of ContentsStudy Guide Table of ContentsABOUT THE AUTHORFrancis A. Carey is a native of Pennsylvania, educatedin the public schools of Philadelphia, at Drexel Univer-sity (B.S. in chemistry, 1959), and at Penn State (Ph.D.1963). Following postdoctoral work at Harvard and mil-itary service, he joined the chemistry faculty of the Uni-versity of Virginia in 1966.With his students, Professor Carey has publishedover 40 research papers in synthetic and mechanisticorganic chemistry. He is coauthor (with Richard J. Sund-berg) of Advanced Organic Chemistry, a two-volumetreatment designed for graduate students and advancedundergraduates, and (with Robert C. Atkins) of OrganicChemistry: A Brief Course, an introductory text for theone-semester organic course.Since 1993, Professor Carey has been a memberof the Committee of Examiners of the Graduate RecordExamination in Chemistry. Not only does he get to par-ticipate in writing the Chemistry GRE, but the annualworking meetings provide a stimulating environment forsharing ideas about what should (and should not) betaught in college chemistry courses.Professor Carey’s main interest shifted fromresearch to undergraduate education in the early 1980s.He regularly teaches both general chemistry and organicchemistry to classes of over 300 students. He enthusi-astically embraces applications of electronic media tochemistry teaching and sees multimedia presentations asthe wave of the present.Frank and his wife Jill, who is a teacher/directorof a preschool and a church organist, are the parents ofthree grown sons and the grandparents of Riyad andAva.| | | |▲▲e-Text Main MenuTextbook Table of ContentsStudy Guide Table of ContentsixBRIEF CONTENTSPreface xxvIntroduction 11 CHEMICAL BONDING 72 ALKANES 533 CONFORMATIONS OF ALKANES AND CYCLOALKANES 894 ALCOHOLS AND ALKYL HALIDES 1265 STRUCTURE AND PREPARATION OF ALKENES: ELIMINATION REACTIONS 1676 REACTIONS OF ALKENES: ADDITION REACTIONS 2087 STEREOCHEMISTRY 2598 NUCLEOPHILIC SUBSTITUTION 3029 ALKYNES 33910 CONJUGATION IN ALKADIENES AND ALLYLIC SYSTEMS 36511 ARENES AND AROMATICITY 39812 REACTIONS OF ARENES: ELECTROPHILIC AROMATIC SUBSTITUTION 44313 SPECTROSCOPY 48714 ORGANOMETALLIC COMPOUNDS 54615 ALCOHOLS, DIOLS, AND THIOLS 57916 ETHERS, EPOXIDES, AND SULFIDES 61917 ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THECARBONYL GROUP 65418 ENOLS AND ENOLATES 70119 CARBOXYLIC ACIDS 73620 CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION 77421 ESTER ENOLATES 83122 AMINES 85823 ARYL HALIDES 91724 PHENOLS 93925 CARBOHYDRATES 97226 LIPIDS 101527 AMINO ACIDS, PEPTIDES, AND PROTEINS. NUCLEIC ACIDS 1051APPENDIX 1 PHYSICAL PROPERTIES A-1APPENDIX 2 ANSWERS TO IN-TEXT PROBLEMS A-9APPENDIX 3 LEARNING CHEMISTRY WITH MOLECULAR MODELS: Using SpartanBuild and SpartanView A-64GLOSSARY G-1CREDITS C-1INDEX I-1| | | |▲▲e-Text Main MenuTextbook Table of ContentsStudy Guide Table of ContentsPREFACExxvPHILOSOPHYFrom its first edition through this, its fourth, OrganicChemistry has been designed to meet the needs of the“mainstream,” two-semester, undergraduate organicchemistry course. It has evolved as those needs havechanged, but its philosophy remains the same. The over-arching theme is that organic chemistry is not only aninteresting subject, but also a logical one. It is logicalbecause its topics can be connected in a steady pro-gression from simple to complex. Our approach hasbeen to reveal the logic of organic chemistry by beingselective in the topics we cover, as well as thorough andpatient in developing them.Teaching at all levels is undergoing rapid change,especially in applying powerful tools that exploit thegraphics capability of personal computers. Organicchemistry has always been the most graphical of thechemical sciences and is well positioned to benefit sig-nificantly from these tools. Consistent with our philoso-phy, this edition uses computer graphics to enhance thecore material, to make it more visual, and more under-standable, but in a way that increases neither the amountof material nor its level.ORGANIZATIONThe central message of chemistry is that the propertiesof a substance come from its structure. What is lessobvious, but very powerful, is the corollary. Someonewith training in chemistry can look at the structure of asubstance and tell you a lot about its properties. Organicchemistry has always been, and continues to be, thebranch of chemistry that best connects structure withproperties. This text has a strong bias toward structure,and this edition benefits from the availability of versa-tile new tools to help us understand that structure.The text is organized to flow logically and step bystep from structure to properties and back again. As thelist of chapter titles reveals, the organization is accord-ing to functional groups—structural units within a mol-ecule most responsible for a particular property—because that is the approach that permits most studentsto grasp the material most readily. Students retain thematerial best, however, if they understand how organicreactions take place. Thus, reaction mechanisms arestressed early and often, but within a functional groupframework. A closer examination of the chapter titlesreveals the close link between a functional group class(Chapter 20, Carboxylic Acid Derivatives) and a reactiontype (Nucleophilic Acyl Substitution), for example. It isvery satisfying to see students who entered the coursebelieving they needed to memorize everything progressto the point of thinking and reasoning mechanistically.Some of the important stages in this approach areas follows:• The first mechanism the students encounter (Chap-ter 4) describes the conversion of alcohols to alkylhalides. Not only is this a useful functional-grouptransformation, but its first step proceeds by thesimplest mechanism of all—proton transfer. Theoverall mechanism provides for an early rein-forcement of acid-base chemistry and an earlyintroduction to carbocations and nucleophilic sub-stitution.• Chapter 5 continues the chemistry of alcohols andalkyl halides by showing how they can be used toprepare alkenes by elimination reactions. Here, thestudents see a second example of the formation ofcarbocation intermediates from alcohols, but inthis case, the carbocation travels a different path-way to a different destination.• The alkenes prepared in Chapter 5 are studiedagain in Chapter 6, this time with an eye towardtheir own chemical reactivity. What the studentslearned about carbocations in Chapters 4 and 5serves them well in understanding the mechanismsof the reactions of alkenes in Chapter 6.• Likewise, the mechanism of nucleophilic addition to the carbonyl group of aldehydes and ketonesdescribed in Chapter 17 sets the stage for aldol con-densation in Chapter 18, esterification of carboxylicacids in Chapter 19, nucleophilic acyl substitution inChapter 20, and ester condensation in Chapter 21.| | | |▲▲e-Text Main MenuTextbook Table of ContentsStudy Guide Table of Contentsxxvi PREFACETHE SPARTAN INTEGRATIONThe third edition of this text broke new ground with itsemphasis on molecular modeling, including the additionof more than 100 exercises of the model-building type.This, the fourth edition, moves to the next level of mod-eling. Gwendolyn and Alan Shusterman’s 1997 Journalof Chemical Education article “Teaching Chemistry withElectron Density Models” described how models show-ing the results of molecular orbital calculations, espe-cially electrostatic potential maps, could be used effec-tively in introductory courses. The software used tocreate the Shustermans’ models was Spartan, a productof Wavefunction, Inc.In a nutshell, the beauty of electrostatic potentialmaps is their ability to display the charge distribution ina molecule. At the most fundamental level, the forcesthat govern structure and properties in organic chemistryare the attractions between opposite charges and therepulsions between like charges. We were therefore opti-mistic that electrostatic potential maps held greatpromise for helping students make the connectionbetween structure, especially electronic structure, andproperties. Even at an early stage we realized that twomain considerations had to guide our efforts.• An integrated approach was required. To be effec-tive, Spartan models and the information they pro-vide must be woven into, not added to, the book’score.• The level of the coverage had to remain the same.Spartan is versatile. We used the same softwarepackage to develop this edition that is used inresearch laboratories worldwide. It was essentialthat we limit ourselves to only those features thatclarified a particular point. Organic chemistry ischallenging enough. We didn’t need to make itmore difficult. If we were to err, it would there-fore be better to err on the side of caution.A third consideration surfaced soon after the workbegan.• Student access to Spartan would be essential.Nothing could help students connect with molec-ular modeling better than owning the same soft-ware used to produce the text or, even better, soft-ware that allowed them not only to view modelsfrom the text, but also to make their own.All of this led to a fruitful and stimulating collab-oration with Dr. Warren Hehre, a leading theoreticalchemist and the founder, president, and CEO of Wave-function, Inc. Warren was enthusiastic about the projectand agreed to actively participate in it. He and AlanShusterman produced a CD tailored specifically toNEW IN THIS EDITIONALL-NEW ILLUSTRATIONS All figures were redrawnto convey visual concepts clearly and forcefully. In ad-dition, the author created a number of new imagesusing the Spartan molecular modeling application.Now students can view electrostatic potential mapsto see the charge distribution of a molecule in vividcolor. These striking images afford the instructor apowerful means to lead students to a better under-standing of organic molecules.FULL SPARTAN IMAGE INTEGRATION The Spartan-generated images are impressive in their own right,but for teaching purposes they are most effectivewhen they are closely aligned with the text content.Because the author personally generated the imagesas he wrote this edition, the molecular models arefully integrated with text, and the educational valueis maximized. Additionally, icons direct students tospecific applications of either the SpartanView orSpartanBuild program, found on the accompanyingCD-ROM. Appendix 3 provides a complete guide tothe Learning By Modeling CD-ROM.ALL-NEW SPECTRA Chapter 13, Spectroscopy, washeavily revised, with rewritten sections on NMR andwith all the NMR spectra generated on a high-fieldinstrument.IMPROVED SUMMARIES The end-of-chapter sum-maries are recast into a more open, easier-to-readformat, inspired by the popularity of the accompany-ing summary tables.NEW DESIGN This edition sports a new look, with anemphasis on neatness, clarity, and color carefullyused to heighten interest and to create visual cues forimportant information.| | | |▲▲e-Text Main MenuTextbook Table of ContentsStudy Guide Table of ContentsPREFACE xxviiaccompany our text. We call it Learning By Modeling.It and Organic Chemistry truly complement each other.Many of the problems in Organic Chemistry have beenwritten expressly for the model-building software Spar-tanBuild that forms one part of Learning By Modeling.Another tool, SpartanView, lets students inspect morethan 250 already constructed models and animations,ranging in size from hydrogen to carboxypeptidase.We were careful to incorporate Spartan so it wouldbe a true amplifier of the textbook, not just as a stand-alone tool that students might or might not use, depend-ing on the involvement of their instructor. Thus, thecontent of the CD provides visual, three-dimensionalreinforcement of the concepts covered on the printedpage. The SpartanView icon invites students to viewa molecule or animation as they are reading the text.Opportunities to use SpartanBuild are similarlycorrelated to the text with an icon directing studentsto further explore a concept or solve a modeling-basedproblem with the software.In addition to its role as the electronic backboneof the CD component and the integrated learningapproach, the Spartan software makes a visible impacton the printed pages of this edition. I used Spartan onmy own computer to create many of the figures, pro-viding students with numerous visual explorations of theconcepts of charge distribution.BIOLOGICAL APPLICATIONS AND THEIRINTEGRATIONComprehensive coverage of the important classes of bio-molecules (carbohydrates, lipids, amino acids, peptides,proteins, and nucleic acids) appears in Chapters 25–27.But biological applications are such an important part oforganic chemistry that they deserve more attentionthroughout the course. We were especially alert to oppor-tunities to introduce more biologically oriented materialto complement that which had already grown signifi-cantly since the first edition. Some specific examples:• The new boxed essay “Methane and the Bio-sphere” in Chapter 2 combines elements oforganic chemistry, biology, and environmental sci-ence to tell the story of where methane comesfrom and where it goes.• A new boxed essay, “An Enzyme-CatalyzedNucleophilic Substitution of an Alkyl Halide,” inChapter 8 makes a direct and simple connectionbetween SN2 reactions and biochemistry.• Two new boxed essays, “How Sweet It Is!” inChapter 25, and “Good Cholesterol? Bad Choles-terol? What’s the Difference?” in Chapter 26,cover topics of current interest from an organicchemist’s perspective.• The already-numerous examples of enzyme-catalyzed organic reactions were supplemented byadding biological Baeyer-Villiger oxidations andfumaric acid dehydrogenation.Chapters 25–27 have benefited substantially fromthe Spartan connection. We replaced many of the artist-rendered structural drawings of complex biomoleculesfrom earlier editions with accurate models generatedfrom imported crystallographic data. These include:• maltose, cellobiose, and cellulose in Chapter 25• triacylglycerols in Chapter 26• alanylglycine, leucine enkephalin, a pleated ␤-sheet, an ␣-helix, carboxypeptidase, myoglobin,DNA, and phenylalanine tRNA in Chapter 27All of these are included on Learning By Model-ing, where you can view them as wire, ball-and-spoke,tube, or space-filling models while rotating them in threedimensions.Both the text and Learning By Modeling includeother structures of biological interest including:• a space-filling model of a micelle (Chapter 19)• electrostatic potential maps of the 20 commonamino acids showing just how different the vari-ous side chains are (Chapter 27)SPECTROSCOPYBecause it offers an integrated treatment of nuclear mag-netic resonance (NMR), infrared (IR), and ultraviolet-visible (UV-VIS) spectroscopy, and mass spectrometry(MS), Chapter 13 is the longest in the text. It is also thechapter that received the most attention in this edition.All of the sections dealing with NMR were extensivelyrewritten, all of the NMR spectra were newly recordedon a high-field instrument, and all of the text figureswere produced directly from the electronic data files.Likewise, the IR and UV-VIS sections of Chapter13 were revised and all of the IR spectra were recordedespecially for this text.After being first presented in Chapter 13, spec-troscopy is then integrated into the topics that follow it.The functional-group chapters, 15, 16, 17, 19, 20, 22,| | | |▲▲e-Text Main MenuTextbook Table of ContentsStudy Guide Table of Contentsxxviii PREFACEand 24, all contain spectroscopy sections as well asexamples and problems based on display spectra.INTEGRATION OF TOPICSToo often, in too many courses (and not just in organicchemistry), too many interesting topics never get cov-ered because they are relegated to the end of the text as“special topic chapters” that, unfortunately, fall by thewayside as the end of the term approaches. We have,from the beginning and with each succeeding edition,looked for opportunities to integrate the most importantof these “special” topics into the core material. I ampleased with the results. Typically, this integration isaccomplished by breaking a topic into its componentelements and linking each of those elements to one ormore conceptually related core topics.There is, for example, no end-of-text chapter enti-tled “Heterocyclic Compounds.” Rather, heteroatomsare defined in Chapter 1 and nonaromatic heterocycliccompounds introduced in Chapter 3; heterocyclic aro-matic compounds are included in Chapter 11, and theirelectrophilic and nucleophilic aromatic substitution reac-tions described in Chapters 12 and 23, respectively. Het-erocyclic compounds appear in numerous ways through-out the text and the biological role of two classes ofthem—the purines and pyrimidines—features promi-nently in the discussion of nucleic acids in Chapter 27.The economic impact of synthetic polymers is toogreat to send them to the end of the book as a separatechapter or to group them with biopolymers. We regardpolymers as a natural part of organic chemistry and payattention to them throughout the text. The preparation ofvinyl polymers is described in Chapter 6, polymer ste-reochemistry in Chapter 7, diene polymers in Chapter10, Ziegler–Natta catalysis in Chapter 14, and conden-sation polymers in Chapter 20.INTEGRATING THE CHEMISTRYCURRICULUMI always thought that the general chemistry coursewould be improved if more organic chemists taught it,and have done just that myself for the past nine years.I now see that just as general chemistry can benefit fromthe perspective that an organic chemist brings to it, socan the teaching and learning of organic chemistry beimproved by making the transition from general chem-istry to organic smoother. Usually this is more a matterof style and terminology than content—an incrementalrather than a radical change. I started making suchchanges in the third edition and continue here.I liked, for example, writing the new boxed essay“Laws, Theories, and the Scientific Method” and placingit in Chapter 6. The scientific method is one thing thateveryone who takes a college-level chemistry courseshould be familiar with, but most aren’t. It normallyappears in Chapter 1 of general chemistry texts, before thestudents have enough factual knowledge to really under-stand it, and it’s rarely mentioned again. By the time ourorganic chemistry students get to “Laws, Theories, and theScientific Method,” however, we have told them about theexperimental observations that led to Markovnikov’s law,and how our understanding has progressed to the level ofa broadly accepted theory based on carbocation stability.It makes a nice story. Let’s use it.FEWER TOPICS EQUALS MORE HELPBy being selective in the topics we cover, we caninclude more material designed to help the student learn.Solved sample problems: In addition to a generousnumber of end-of-chapter problems, the textincludes more than 450 problems within the chap-ters themselves. Of these in-chapter problemsapproximately one-third are multipart exercisesthat contain a detailed solution to part (a) outlin-ing the reasoning behind the answer.Summary tables: Annotated summary tables havebeen a staple of Organic Chemistry ever since thefirst edition and have increased in number to morethan 50. Well received by students and facultyalike, they remain one of the text’s strengths.End-of-chapter summaries: Our experience with thesummary tables prompted us to recast the narra-tive part of the end-of-chapter summaries into amore open, easier-to-read format.SUPPLEMENTSFor the StudentStudy Guide and Solutions Manual by Francis A.Carey and Robert C. Atkins. This valuable supplementprovides solutions to all problems in the text. More thansimply providing answers, most solutions guide the stu-dent with the reasoning behind each problem. In addi-tion, each chapter of the Study Guide and SolutionsManual concludes with a Self-Test designed to assessthe student’s mastery of the material.Online Learning CenterAt www.mhhe.com/carey, this comprehensive, exclusiveWeb site provides a wealth of electronic resources for| | | |▲▲e-Text Main MenuTextbook Table of ContentsStudy Guide Table of ContentsPREFACE xxixinstructors and students alike. Content includes tutorials,problem-solving strategies, and assessment exercises forevery chapter in the text.Learning By Modeling CD-ROMIn collaboration with Wavefunction, we have created across-function CD-ROM that contains an electronicmodel-building kit and a rich collection of animationsand molecular models that reveal the interplay betweenelectronic structure and reactivity in organic chemistry.Packaged free with the text, Learning By Model-ing has two components: SpartanBuild, a user-friendlyelectronic toolbox that lets you build, examine, and eval-uate literally thousands of molecular models; and Spar-tanView, an application with which you can view andexamine more than 250 molecular models and anima-tions discussed in the text. In the textbook, icons pointthe way to where you can use these state-of-the-art mol-ecular modeling applications to expand your under-standing and sharpen your conceptual skills. This edi-tion of the text contains numerous problems that takeadvantage of these applications. Appendix 3 provides acomplete guide to using the CD.For the InstructorOverhead Transparencies. These full-color transparen-cies of illustrations from the text include reproductionsof spectra, orbital diagrams, key tables, computer-generated molecular models, and step-by-step reactionmechanisms.Test Bank. This collection of 1000 multiple-choice questions, prepared by Professor Bruce Osterbyof the University of Wisconsin–LaCrosse, is available toadopters in print, Macintosh, or Windows format.Visual Resource Library. This invaluable lectureaid provides the instructor with all the images from thetextbook on a CD-ROM. The PowerPoint formatenables easy customization and formatting of the imagesinto the lecture.The Online Learning Center, described in the pre-vious section, has special features for instructors, includ-ing quiz capabilities.Please contact your McGraw-Hill representativefor additional information concerning these supple-ments.| | | |▲▲e-Text Main MenuTextbook Table of ContentsStudy Guide Table of ContentsACKNOWLEDGMENTSxxxiYou may have noticed that this preface is almost entirely“we” and “our,” not “I” and “my.” That is becauseOrganic Chemistry is, and always has been, a teameffort. From the first edition to this one, the editorial andproduction staffs at WCB/McGraw-Hill have been com-mitted to creating an accurate, interesting, student-oriented text. Special thanks go to Kent Peterson, TerryStanton, and Peggy Selle for their professionalism, skill,and cooperative spirit. Linda Davoli not only copyedited the manuscript but offered valuable advice aboutstyle and presentation. GTS Graphics had the critical jobof converting the copy-edited manuscript to a real book.Our contact there was Heather Stratton; her enthusiasmfor the project provided us an unusual amount of free-dom to fine-tune the text.I have already mentioned the vital role played byWarren Hehre and Alan Shusterman in integrating Spar-tan into this edition. I am grateful for their generosity ingiving their time, knowledge, and support to this proj-ect. I also thank Dr. Michal Sabat of the University ofVirginia for his assistance in my own modeling efforts.All of the NMR and IR spectra in this edition wererecorded at the Department of Chemistry of JamesMadison University by two undergraduate students, Jef-frey Cross and Karin Hamburger, under the guidance ofThomas Gallaher. We are indebted to them for theirhelp.Again, as in the three previous editions, Dr. RobertC. Atkins has been indispensable. Bob is the drivingforce behind the Study Guide and Solutions Manual thataccompanies this text. He is much more than that,though. He reads and critiques every page of the man-uscript and every page of two rounds of proofs. I trusthis judgment completely when he suggests how to sim-plify a point or make it clearer. Most of all, he is a greatfriend.This text has benefited from the comments offeredby a large number of teachers of organic chemistry whoreviewed it at various stages of its development. I appre-ciate their help. They includeReviewers for the Fourth EditionJennifer Adamski, Old Dominion UniversityJeffrey B. Arterburn, New Mexico State UniversitySteven Bachrach, Trinity UniversityJared A. Butcher, Jr., Ohio UniversityBarry Carpenter, Cornell UniversityPasquale R. Di Raddo, Ferris State UniversityJill Discordia, Le Moyne CollegeWilliam A. Donaldson, Marquette UniversityMark Forman, St. Joseph’s UniversityWarren Giering, Boston UniversityBenjamin Gross, University of Tennessee–ChattanoogaR. J. Hargrove, Mercer UniversityE. Alexander Hill, University of Wisconsin–MilwaukeeShawn Hitchcock, Illinois State UniversityL. A. Hull, Union CollegeColleen Kelley, Northern Arizona UniversityBrenda Kesler, San Jose State UniversityC. A. Kingsbury, University of Nebraska–LincolnFrancis M. Klein, Creighton UniversityPaul M. Lahti, University of Massachusetts–AmherstRita S. Majerle, South Dakota State UniversityMichael Millam, Phoenix CollegeTyra Montgomery, University of Houston–DowntownRichard Narske, Augustana UniversityMichael A. Nichols, John Carroll UniversityBruce E. Norcross, SUNY–BinghamtonCharles A. Panetta, University of MississippiMichael J. Panigot, Arkansas State UniversityJoe Pavelites, William Woods CollegeTy Redd, Southern Utah UniversityCharles Rose, University of NevadaSuzanne Ruder, Virginia Commonwealth UniversityChristine M. Russell, College of DuPageDennis A. Sardella, Boston CollegeJanice G. Smith, Mt. Holyoke CollegeTami I. Spector, University of San FranciscoKen Turnbull, Wright State UniversityClifford M. Utermoehlen, USAF AcademyCurt Wentrup, University of QueenslandS. D. Worley, Auburn UniversityReviewers for the Third EditionEdward Alexander, San Diego Mesa CollegeRonald Baumgarten, University of Illinois–ChicagoBarry Carpenter, Cornell UniversityJohn Cochran, Colgate University| | | |▲▲e-Text Main MenuTextbook Table of ContentsStudy Guide Table of Contents[...]... shown was issued in 1971 by Argentina | COMPUTERS AND ORGANIC CHEMISTRY A familiar arrangement of the sciences places chemistry between physics, which is highly mathematical, and biology, which is highly descriptive Among chemistry s subdisci- e-Text Main Menu | Textbook Table of Contents | Study Guide Table of Contents Introduction plines, organic chemistry is less mathematical than descriptive in that... fundamentally different from inorganic compounds; it was believed inorganic compounds could be synthesized in the laboratory, but organic compounds could not—at least not from inorganic materials In 1823, Friedrich Wöhler, fresh from completing his medical studies in Germany, traveled to Stockholm to study under Berzelius A year later Wöhler accepted a position teaching chemistry and conducting research... cyanate (an inorganic compound) OœC(NH2)2 ± £ Urea (an organic compound) The transformation observed by Wöhler was one in which an inorganic salt, ammonium cyanate, was converted to urea, a known organic substance earlier isolated from urine This experiment is now recognized as a scientific milestone, the first step toward overturning the philosophy of vitalism Although Wöhler’s synthesis of an organic compound... were burned in air By the time of Lavoisier’s studies, two branches of chemistry were becoming recognized One branch was concerned with matter obtained from natural or living sources and was called organic chemistry The other branch dealt with substances derived from nonliving matter—minerals and the like It was called inorganic chemistry Combustion analysis soon established that the compounds derived... same journal (pp 883–886) chemistry It was he who in 1807 coined the term organic chemistry for the study of compounds derived from natural sources Berzelius, like almost everyone else at the time, subscribed to the doctrine known as vitalism Vitalism held that living systems possessed a “vital force” which was absent in nonliving systems Compounds derived from natural sources (organic) were thought... focusing on electrons In effect, Robinson analyzed organic reactions by looking at the electrons and understood that atoms moved because they were carried along by the transfer of electrons Ingold applied the quantitative methods of physical chemistry to the study of organic reactions so as to better understand the sequence of events, the mechanism, by which an organic substance is converted to a product... reactions of organic chemistry have been scrutinized to the degree that we have a relatively clear picture of the intermediates that occur during the passage of starting materials to products Extension of the principles of mechanism to reactions that occur in living systems, on the other hand, is an area in which a large number of important questions remain to be answered THE INFLUENCE OF ORGANIC CHEMISTRY. .. blood pressure We now know that it contains ephedrine, an organic compound similar in structure and physiological activity to adrenaline, a hormone secreted by the adrenal gland Almost all drugs prescribed today for the treatment of disease are organic compounds—some are derived from natural sources; many others are the products of synthetic organic chemistry As early as 2500 BC in India, indigo was used... and the like It was called inorganic chemistry Combustion analysis soon established that the compounds derived from natural sources contained carbon, and eventually a new definition of organic chemistry emerged: organic chemistry is the study of carbon compounds This is the definition we still use today BERZELIUS, WÖHLER, AND VITALISM As the eighteenth century gave way to the nineteenth, Jöns Jacob Berzelius... of greater efficacy The influence of computers on the practice of organic chemistry is a significant recent development and will be revisited numerous times in the chapters that follow 5 A DNA double helix as pictured on a 1964 postage stamp issued by Israel CHALLENGES AND OPPORTUNITIES | L L A major contributor to the growth of organic chemistry during this century has been the accessibility of cheap . Francis A. Organic chemistry / Francis A. Carey. — 4th ed.p. cm.Includes index.ISBN 0-07-290501-8 — ISBN 0-07-117499-0 (ISE)1. Chemistry, Organic. I papers in synthetic and mechanistic organic chemistry. He is coauthor (with Richard J. Sund-berg) of Advanced Organic Chemistry, a two-volumetreatment
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