《有机化学》课程教学资源（教材文献，英文版）ORGANIC CHEMISTRY

PREFACE THE SPARTAN INTEGRATION vide must be woven into. not added to. the books The third edition of this text broke new ground with its emphasis on molecular modeling, including the addition The level of the coverage had to remain the same. of more than 100 exercises of the model-building type Spartan is versatile. We used the same software This. the fourth edition. moves to the next level of mod package to develop this edition that is used in eling. Gwendolyn and Alan Shusterman's 1997 Journal research laboratories worldwide. It was essential of Chemical Education article "Teaching Chemistry with that we limit ourselves to only those features that Electron Density Models"described how models show- clarified a particular point. Organic chemistry is ing the results of molecular orbital calculations, espe challenging enough. We didnt need to make it ally electrostatic potential maps, could be used effec- difficult. If we were to err. it would there. tively in introductory courses. The software used to fore be better to err on the side of caution create the Shustermans'models was Spartan, a product of wavefunction. Inc. a third consideration surfaced soon after the work In a nutshell, the beauty of electrostatic potential maps is their ability to display the charge distribution in Student access to Spartan would be essential. a molecule. At the most fundamental level. the forces ing could help students connect with molec- that govern structure and properties in organic chemistry ular modeling better than owning the same soft are the attractions between opposite charges and the ware used to produce the text or, even better, soft repulsions between like charges. We were therefore opti ware that allowed them not only to view models mistic that electrostatic potential maps held great from the text but also to make their own. promise for helping students make the connection between structure, especially electronic structure, and All of this led to a fruitful and stimulating collab- properties. Even at an early stage we realized that tw oration with Dr. Warren Hehre. a leading theoretical main considerations had to guide our efforts chemist and the founder, president, and CEO of Wave- function, Inc. Warren was enthusiastic about the project An integrated approach was required. To be effec- and agreed to actively participate in it. He and Alan tive, Spartan models and the information they pro- Shusterman produced a CD tailored specifically to NEW IN THIS EDITION ALL-NEW ILLUSTRATIONS All figures were redrawn specific applications of either the Spartanview or to convey visual concepts clearly and forcefully In ad- Spartan Build program, found on the accompanying dition, the author created a number of new image les CD-ROM. Appendix 3 provides a complete guide to using the Spartan molecular modeling application. the Learning By Modeling CD-ROM Now students can view electrostatic potential maps to see the charge distribution of a molecule in vivid ALL-NEW SPECTRA Chapter 13, Spectroscopy, was color. These striking images afford the instructor a heavily revised, with rewritten sections on NMR and powerful means to lead students to a better under with all the NMR spectra generated on a high-fie standing of organic molecules Instrument FULL SPARTAN IMAGE INTEGRATION The Spartan- maries are recast into a more open, easier-to-read generated images are impressive in their own right, format, inspired by the popularity of the accompany- but for teaching purposes they are most effective when they are closely aligned with the text content. g summary tables Because the author personally generated the images NEW DESIGN This edition sports a new look, with an as he wrote this edition, the molecular models are emphasis on neatness, clarity, and color carefully lly integrated with text, and the educational value used to heighten interest and to create visual cues for is maximized. Additionally, icons direct students to important information. Forward Main Menu TOC Study Guide Toc Student OLCMHHE Website

xxvi PREFACE THE SPARTAN INTEGRATION The third edition of this text broke new ground with its emphasis on molecular modeling, including the addition of 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 Journal of Chemical Education article “Teaching Chemistry with Electron 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 to create the Shustermans’ models was Spartan, a product of Wavefunction, Inc. In a nutshell, the beauty of electrostatic potential maps is their ability to display the charge distribution in a molecule. At the most fundamental level, the forces that govern structure and properties in organic chemistry are the attractions between opposite charges and the repulsions between like charges. We were therefore opti￾mistic that electrostatic potential maps held great promise for helping students make the connection between structure, especially electronic structure, and properties. Even at an early stage we realized that two main 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’s core. • The level of the coverage had to remain the same. Spartan is versatile. We used the same software package to develop this edition that is used in research laboratories worldwide. It was essential that we limit ourselves to only those features that clarified a particular point. Organic chemistry is challenging enough. We didn’t need to make it more 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 work began. • 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 models from 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 theoretical chemist and the founder, president, and CEO of Wave￾function, Inc. Warren was enthusiastic about the project and agreed to actively participate in it. He and Alan Shusterman produced a CD tailored specifically to NEW IN THIS EDITION ALL-NEW ILLUSTRATIONS All figures were redrawn to convey visual concepts clearly and forcefully. In ad￾dition, the author created a number of new images using the Spartan molecular modeling application. Now students can view electrostatic potential maps to see the charge distribution of a molecule in vivid color. These striking images afford the instructor a powerful 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 effective when they are closely aligned with the text content. Because the author personally generated the images as he wrote this edition, the molecular models are fully integrated with text, and the educational value is maximized. Additionally, icons direct students to specific applications of either the SpartanView or SpartanBuild program, found on the accompanying CD-ROM. Appendix 3 provides a complete guide to the Learning By Modeling CD-ROM. ALL-NEW SPECTRA Chapter 13, Spectroscopy, was heavily revised, with rewritten sections on NMR and with all the NMR spectra generated on a high-field instrument. IMPROVED SUMMARIES The end-of-chapter sum￾maries are recast into a more open, easier-to-read format, inspired by the popularity of the accompany￾ing summary tables. NEW DESIGN This edition sports a new look, with an emphasis on neatness, clarity, and color carefully used to heighten interest and to create visual cues for important information

PREFACE accompany our text. We call it Learning By Modelin Two new boxed essays, "How Sweet It Is! "in It and Organic Chemistry truly complement each other. hapter 25, and"Good Cholesterol? Bad Choles Many of the problems in Organic Chemistry have been terol? What's the Difference? "in Chapter 26 written expressly for the model-building software Spar cover topics of current interest from an organic tan Build that forms one part of Learning By Modeling chemists perspective Another tool, Spartan View, lets students inspect more than 250 already constructed models and animations The already-numerous examples of enzyme catalyzed organic reactions were supplemented by ranging in size from hydrogen to carboxypeptidase adding biological Baeyer-Villiger oxidations and We were careful to incorporate Spartan so it would fumaric acid dehydrogenation be a true amplifier of the textbook, not just as a stand alone tool that students might or might not use, depend- Chapters 25-27 have benefited substantially from ng on the involvement of their instructor. Thus, the the Spartan connection. We replaced many of the artist- content of the CD provides visual, three-dimensional rendered structural drawings of complex biomolecules reinforcement of the concepts covered on the printe from earlier editions with accurate models generated page. The Spartan View icon O invites students to view from imported crystallographic data. These include a molecule or animation as they are reading the text. maltose, cellobiose, and cellulose in Chapter 25 Opportunities to use Spartan Build are similarly correlated to the text with an icon 2 directing students triacylglycerols in Chapter 26 to further explore a concept or solve a modeling-based alanylglycine, leucine enkephalin, a pleated B- problem with the software sheet, an a-helix, carboxypeptidase, myoglobin, In addition to its role as the electronic backbone DNA, and phenylalanine tRNA in Chapter 27 of the CD component and the integrated learnin All of these are included on Learning By Model- approach, the Spartan software makes a visible impact ing, where you can view them as wire, ball-and-spoke on the printed pages of this edition. I used Spartan or tube, or space-filling models while rotating them in three my own computer to create many of the figures, pro- dimensions viding students with numerous visual explorations of the Both the text and Learning by modeling include oncepts of charge distribution other structures of biological interest including BIOLOGICAL APPLICATIONS AND THEIR electrostatic potential maps of the 20 common INTEGRATION amino acids showing just how different the vari- Comprehensive coverage of the important classes of bio- ous side chains are( Chapter 27) molecules(carbohydrates, lipids, amino acids, peptides proteins, and nucleic acids) appears in Chapters 25-27. SPECTROSCOPY But biological applications are such an important part of organ hemistry that they deserve more attention Because it offers an integrated treatment of nuclear mag- throughout the course. We were especially alert to oppor- netic resonance(NMR), infrared (IR), and ultraviolet tunities to introduce more biologically oriented material visible (Uv-vIS) spectroscopy, and mass spectrometry to complement that which had already grown signifi- (MS), Chapter 13 is the longest in the text. It is also the cantly since the first edition. Some specific examples chapter that received the most attention in this edition All of the sections dealing with NMR were extensively The new boxed essay"Methane and the Bio- rewritten, all of the NMR spectra were newly recorded sphere"in Chapter 2 combines elements of on a high-field instrument, and all of the text figures organic chemistry, biology, and environmental sci- were produced directly from the electronic data files ence to tell the story of where methane comes Likewise, the IR and UV-VIs sections of Chapter from and where it goes 13 were revised and all of the IR spectra were recorded A new boxed essay,"An Enzyme-Catalyzed especially for this text. Nucleophilic Substitution of an Alkyl Halide, in After being first presented in Chapter 13, spec Chapter 8 makes a direct and simple connection troscopy is then integrated into the topics that follow it between SN2 reactions and biochemistry. The functional-group chapters, 15, 16, 17, Forward Main Menu TOC Study Guide Toc Student OLCMHHE Website

PREFACE xxvii accompany our text. We call it Learning By Modeling. It and Organic Chemistry truly complement each other. Many of the problems in Organic Chemistry have been written expressly for the model-building software Spar￾tanBuild that forms one part of Learning By Modeling. Another tool, SpartanView, lets students inspect more than 250 already constructed models and animations, ranging in size from hydrogen to carboxypeptidase. We were careful to incorporate Spartan so it would be 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, the content of the CD provides visual, three-dimensional reinforcement of the concepts covered on the printed page. The SpartanView icon invites students to view a molecule or animation as they are reading the text. Opportunities to use SpartanBuild are similarly correlated to the text with an icon directing students to further explore a concept or solve a modeling-based problem with the software. In addition to its role as the electronic backbone of the CD component and the integrated learning approach, the Spartan software makes a visible impact on the printed pages of this edition. I used Spartan on my own computer to create many of the figures, pro￾viding students with numerous visual explorations of the concepts of charge distribution. BIOLOGICAL APPLICATIONS AND THEIR INTEGRATION Comprehensive 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 of organic chemistry that they deserve more attention throughout the course. We were especially alert to oppor￾tunities to introduce more biologically oriented material to 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 of organic chemistry, biology, and environmental sci￾ence to tell the story of where methane comes from and where it goes. • A new boxed essay, “An Enzyme-Catalyzed Nucleophilic Substitution of an Alkyl Halide,” in Chapter 8 makes a direct and simple connection between SN2 reactions and biochemistry. • Two new boxed essays, “How Sweet It Is!” in Chapter 25, and “Good Cholesterol? Bad Choles￾terol? What’s the Difference?” in Chapter 26, cover topics of current interest from an organic chemist’s perspective. • The already-numerous examples of enzyme￾catalyzed organic reactions were supplemented by adding biological Baeyer-Villiger oxidations and fumaric acid dehydrogenation. Chapters 25–27 have benefited substantially from the Spartan connection. We replaced many of the artist￾rendered structural drawings of complex biomolecules from earlier editions with accurate models generated from 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 27 All 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 three dimensions. Both the text and Learning By Modeling include other structures of biological interest including: • a space-filling model of a micelle (Chapter 19) • electrostatic potential maps of the 20 common amino acids showing just how different the vari￾ous side chains are (Chapter 27) SPECTROSCOPY Because 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 the chapter that received the most attention in this edition. All of the sections dealing with NMR were extensively rewritten, all of the NMR spectra were newly recorded on a high-field instrument, and all of the text figures were produced directly from the electronic data files. Likewise, the IR and UV-VIS sections of Chapter 13 were revised and all of the IR spectra were recorded especially 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,

PREFACE and 24, all contain spectroscopy sections as well as I liked, for example, writing the new boxed essay examples and problems based on display spectra. Laws, Theories, and the Scientific Method"and placing it in Chapter 6. The scientific method is one thing that NTEGRATION OF TOPICS who takes a college-level chemistry should be familiar with. but most arent. It normall Too often, in too many courses(and not just in organic appears in Chapter I of general chemistry texts, before the chemistry), too many interesting topics never get cov students have enough factual knowledge to really under- ered because they are relegated to the end of the text as stand it, and it's rarely mentioned again. By the time our special topic chapters"that, unfortunately, fall by the organic chemistry students get to"Laws, Theories, and the wayside as the end of the term approaches. We have Scientific Method, however, we have told them about the from the beginning and with each succeeding edition experimental observations that led to Markovnikov's law, looked for opportunities to integrate the most important ng has prog of these"special topics into the core material. I am a broadly accepted theory based on carbocation stability pleased with the results. Typically, this integration is It makes a nice story. Lets use it accomplished by breaking a topic into its component elements and linking each of those elements to one or FEWER TOPICS EQUALS MORE HELP more conceptually related core topics There is, for example, no end-of-text chapter enti- By being selective in the topics we cover, we can tled"Heterocyclic Compounds. Rather, heteroatoms include more material designed to help the student learn. are defined in Chapter 1 and nonaromatic heterocyclic Solved sample problems: In addition to a generous number of end-of-chapter problems, the text electrophilic and nucleophilic aromatic substitution reac includes more than 450 problems within the chap- tions described in Chapters 12 and 23, respectively. Het- rs themselves. Of these in-chapter problems rocyclic compounds appear in numerous ways througl approximately one-third are multipart exercises out the text and the biological role of two classes of that contain a detailed solution to part (a) outlin- them-the purines and pyrimidines--features promi ing the reasoning behind the answer. nently in the discussion of nucleic acids in Chapter 27 Summary tables: Annotated summary tables have he economic impact of synthetic polymers is too been a staple of Organic Chemistry ever since the great to send them to the end of the book as a separate first edition and have increased in number to more chapter or to group them with biopolymers. We regard than 50. Well received by students and faculty polymers as a natural part of organic chemistry and pay alike, they remain one of the texts strengths attention to them throughout the text. The prepara End-of-chapter summaries: Our with the vinyl polymers is described in Chapter 6, poly summary tables prompted us to recast the narra- geochemistry in Chapter 7, diene polymers in tive part of the end-of-chapter summaries into a 10, Ziegler-Natta catalysis in Chapter 14, and conder more open, easier-to-read format sation polymers in Chapter 20 SUPPLEMENTS INTEGRATING THE CHEMISTRY CURRICULUM For the student Study Guide and Solutions Manual by Francis A I always thought that the general chemistry course Carey and Robert C. Atkins. This valuable supplement would be improved if more organic chemists taught it, provides solutions to all problems in the text. More than and have done just that myself for the past nine years imply providing answers, most solutions guide the stu I now see that just as general chemistry can benefit from dent with the reasoning behind each problem. In addi the perspective that an organic chemist brings to it, so tion, each chapter of the Study Guide and Solutions can the teaching and learning of organic chemistry be Manual concludes with a Self- Test designed to assess improved by making the transition from general chem- the students mastery of the material istry to organic smoother. Usually this is more a matter of style and terminology than content-an incremental Online Learning Center atherthanaradicalchangeIstartedmakingsuchAtwww.mhhe.com/carey,thiscomprehensiveexclusive changes in the third edition and continue here Web site provides a wealth of electronic resources for Forward Main Menu TOC Study Guide Toc Student OLCMHHE Website

xxviii PREFACE and 24, all contain spectroscopy sections as well as examples and problems based on display spectra. INTEGRATION OF TOPICS Too often, in too many courses (and not just in organic chemistry), 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 the wayside as the end of the term approaches. We have, from the beginning and with each succeeding edition, looked for opportunities to integrate the most important of these “special” topics into the core material. I am pleased with the results. Typically, this integration is accomplished by breaking a topic into its component elements and linking each of those elements to one or more conceptually related core topics. There is, for example, no end-of-text chapter enti￾tled “Heterocyclic Compounds.” Rather, heteroatoms are defined in Chapter 1 and nonaromatic heterocyclic compounds introduced in Chapter 3; heterocyclic aro￾matic compounds are included in Chapter 11, and their electrophilic 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 of them—the purines and pyrimidines—features promi￾nently in the discussion of nucleic acids in Chapter 27. The economic impact of synthetic polymers is too great to send them to the end of the book as a separate chapter or to group them with biopolymers. We regard polymers as a natural part of organic chemistry and pay attention to them throughout the text. The preparation of vinyl polymers is described in Chapter 6, polymer ste￾reochemistry in Chapter 7, diene polymers in Chapter 10, Ziegler–Natta catalysis in Chapter 14, and conden￾sation polymers in Chapter 20. INTEGRATING THE CHEMISTRY CURRICULUM I always thought that the general chemistry course would 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 from the perspective that an organic chemist brings to it, so can the teaching and learning of organic chemistry be improved by making the transition from general chem￾istry to organic smoother. Usually this is more a matter of style and terminology than content—an incremental rather than a radical change. I started making such changes in the third edition and continue here. I liked, for example, writing the new boxed essay “Laws, Theories, and the Scientific Method” and placing it in Chapter 6. The scientific method is one thing that everyone who takes a college-level chemistry course should be familiar with, but most aren’t. It normally appears in Chapter 1 of general chemistry texts, before the students have enough factual knowledge to really under￾stand it, and it’s rarely mentioned again. By the time our organic chemistry students get to “Laws, Theories, and the Scientific Method,” however, we have told them about the experimental observations that led to Markovnikov’s law, and how our understanding has progressed to the level of a broadly accepted theory based on carbocation stability. It makes a nice story. Let’s use it. FEWER TOPICS EQUALS MORE HELP By being selective in the topics we cover, we can include more material designed to help the student learn. Solved sample problems: In addition to a generous number of end-of-chapter problems, the text includes more than 450 problems within the chap￾ters themselves. Of these in-chapter problems approximately one-third are multipart exercises that contain a detailed solution to part (a) outlin￾ing the reasoning behind the answer. Summary tables: Annotated summary tables have been a staple of Organic Chemistry ever since the first edition and have increased in number to more than 50. Well received by students and faculty alike, they remain one of the text’s strengths. End-of-chapter summaries: Our experience with the summary tables prompted us to recast the narra￾tive part of the end-of-chapter summaries into a more open, easier-to-read format. SUPPLEMENTS For the Student Study Guide and Solutions Manual by Francis A. Carey and Robert C. Atkins. This valuable supplement provides solutions to all problems in the text. More than simply providing answers, most solutions guide the stu￾dent with the reasoning behind each problem. In addi￾tion, each chapter of the Study Guide and Solutions Manual concludes with a Self-Test designed to assess the student’s mastery of the material. Online Learning Center At www.mhhe.com/carey, this comprehensive, exclusive Web site provides a wealth of electronic resources for