上海交通大学：《大学化学》教学资源（参考电子书）《ORGANIC CHEMISTRY》FOURTH EDITION

xxiv PREFACE TO THE FOURTH EDITION change and often to track the fates of atoms and groups in reactions.We have used text bubbles to show important steps in a process or to note an important point. CONVENTION ALERT One factor that can make organic chemistry difficult is that new language must be learned.Organic chemists talk to each other using many different conventions and at least some of that language must be learned or communication is impossi- ble.In addition to general treatments of nomenclature at the beginning of many chapters,we have incorporated numerous Convention Alerts in which aspects of the language that chemists use are highlighted. Throughout the book,reference is made to the connection between organic chemistry and the world of biology.Almost every chapter has a section devoted to the biological relevance of new reactions discussed.We have also added Applications Boxes to illustrate the relevance of the subject to students'lives. CHOLESTEROL FORMATION Sometimes,our well-being depends on interfering with artery,which can result from high levels of LDL cholesterol, an enzyme-mediated rate acceleration.Cholesterol (p.121) are shown below.The benefit of taking a statin drug is a sig- is formed in the body by a lengthy process in which the nificant reduction in the risk of heart attacks and strokes. thioester A is reduced to mevalonic acid,which is then The statins function by inhibiting the enzyme HMG- converted in a series of reactions into cholesterol. CoA reductase,which is involved in the rate-limiting or Controlling cholesterol levels in the body is an important slowest step in the formation of mevalonic acid,and hence part of healthy living.Recent advances in medicinal and cholesterol.Without the enzyme,the reduction to mevalonic organic chemistry have allowed the development of the acid in the body is much too slow.We have learned about "statin"drugs (i.c.,atorvastatin,fluvastatin,lovastatin,pravas- hydride reagents (p.315),and we do have biological hydride tatin,simvastatin,and rosuvastatin),which act to reduce the sources.You will meet one,NADH,in Chapter 16.But simply level of"unhealthy"low-density lipoprotein (LDL)choles- mixing this"natural"hydride reagent with the HMG-CoA terol Examples of a healthy artery anda partially clogged thioester A results in no reaction.However,HMG-CoA reductase can bring the hydride source and the thioester A together in a fashion that allows the reaction to occur.The energy barrier for the reaction is lowered,and mevalonic acid formed and goes on to make cholesterol.The statins inter- fere with the reduction by inhibiting the enzyme necessary- no reduction,no cholesterol! 3-Hydroxy-3-methylglutaryl (or HMG) CoA rate-limiting HMG-CoA step reductase HO、 OH 0 Mevalonic acid steps Cholesterol

change and often to track the fates of atoms and groups in reactions. We have used text bubbles to show important steps in a process or to note an important point. One factor that can make organic chemistry difficult is that new language must be learned. Organic chemists talk to each other using many different conventions and at least some of that language must be learned or communication is impossi￾ble. In addition to general treatments of nomenclature at the beginning of many chapters, we have incorporated numerous Convention Alerts in which aspects of the language that chemists use are highlighted. Throughout the book, reference is made to the connection between organic chemistry and the world of biology. Almost every chapter has a section devoted to the biological relevance of new reactions discussed.We have also added Applications Boxes to illustrate the relevance of the subject to students’ lives. xxiv PREFACE TO THE FOURTH EDITION CONVENTION ALERT 3-Hydroxy-3-methylglutaryl (or HMG) Mevalonic acid Cholesterol CoA HMG-CoA reductase rate-limiting step many steps OH O O– –O HO A NH2 N O– O OH S O N H N H OH N O N O O O O– P O O O H H H H O O– P O OH O– P O N CHOLESTEROL FORMATION Sometimes, our well-being depends on interfering with an enzyme-mediated rate acceleration. Cholesterol (p. 121) is formed in the body by a lengthy process in which the thioester A is reduced to mevalonic acid, which is then converted in a series of reactions into cholesterol. Controlling cholesterol levels in the body is an important part of healthy living. Recent advances in medicinal and organic chemistry have allowed the development of the “statin” drugs (i.e., atorvastatin, fluvastatin, lovastatin, pravas￾tatin, simvastatin, and rosuvastatin), which act to reduce the level of “unhealthy” low-density lipoprotein (LDL) choles￾terol. Examples of a healthy artery and a partially clogged artery, which can result from high levels of LDL cholesterol, are shown below. The benefit of taking a statin drug is a sig￾nificant reduction in the risk of heart attacks and strokes. The statins function by inhibiting the enzyme HMG￾CoA reductase, which is involved in the rate-limiting or slowest step in the formation of mevalonic acid, and hence cholesterol. Without the enzyme, the reduction to mevalonic acid in the body is much too slow. We have learned about hydride reagents (p. 315), and we do have biological hydride sources. You will meet one, NADH, in Chapter 16. But simply mixing this “natural” hydride reagent with the HMG-CoA thioester A results in no reaction. However, HMG-CoA reductase can bring the hydride source and the thioester A together in a fashion that allows the reaction to occur. The energy barrier for the reaction is lowered, and mevalonic acid is formed and goes on to make cholesterol. The statins inter￾fere with the reduction by inhibiting the enzyme necessary— no reduction, no cholesterol! 8 10 S

PREFACE TO THE FOURTH EDITION XXV It can be a great help to be shown profitable(and unprofitable)approaches to problem solving,and the PROBLEM SOLVING number of Problem Solving sections has greatly Whenever you see the word rate"in a problem,or when you see words such as increased in the fourth edition.Although there is no "faster"that talk about rates,you are very likely to have to answer the question by substitute for a thorough understanding of the ma- drawing the transition state for the reaction.Remember that the rate of a terial,our subject is an experience-intensive one,and reaction is determined by AG,the energy difference between starting material and the transition state,and not by the energy difference between starting by definition students are short on that commodity. material and product.You need a pull-down menu that says,"Think about the There are many moments in organic chemistry transition state"when the word "rate"appears in a problem. when it is important to take stock of where we are. Summary sections have been incorporated into every chapter.Here the narrative is broken and the reader is brought up to date on the important points of the previous topic.These summaries serve as excellent"reminder and review"sections when a student is studying for an exam. Each chapter ends with a summary of New Concepts,Key Terms,new Reactions,Mechanisms,and Tools,new Syntheses,and Common Errors.These sections recapitulate and reinforce the material of the chapter,and serve as excellent study tools. We incorporate unsolved problems in two ways.There are many such problems scattered throughout the text and more problems,of all degrees of difficulty,are found at the end of each chapter.They range from drill exercises and simple examples, designed to emphasize important skills and illustrate techniques,to sophisticated, challenging problems.In those last cases,we are careful to provide hints and refer- ences to material useful for the solution.All these problems are solved in the Study Guide,which does much more than provide a bare-bones answer.It,along with the new Problem Solving sections in the fourth edition,tries to show students prob- lem-solving techniques that will help them solve future problems.There are also many solved problems in the text,each designed to reinforce a point just made. The fourth edition contains many new problems including ones that require the use of the Organic Reactions Animations software. Highlights of the Content and Organizational Changes in the Fourth Edition The fourth edition has: A much more complete discussion of resonance in Chapter 1.This change is in response to a request by reviewers who felt this central theme should be presented as early as possible.We agree.Understanding resonance structures is critical,and early coverage provides a strong foundation.The student will have a chance to review the topic in Chapter 9. .A reorganization of Chapter 15.The new outline emphasizes important topics in NMR spectroscopy.Also,the chapter was modified so that it is even more movable than it was in the third edition,in case the instructor wants to present spectroscopy early in the first semester.We believe spectroscopy is a topic that should be taught early.Students can use the tools(UV,IR,NMR,MS)to help understand symme- try,resonance,electronegativity,aromaticity,acidity,and reactivity of molecules. Spectroscopy is an important tool to link structure and activity. Enolates discussed as a single topic in Chapter 19.Earlier editions of this text had the enolate topic covered in two chapters separated by a chapter on carboxylic acids. Because enolates of aldehydes,ketones,esters,and carboxylic acids all share similar

It can be a great help to be shown profitable (and unprofitable) approaches to problem solving, and the number of Problem Solving sections has greatly increased in the fourth edition. Although there is no substitute for a thorough understanding of the ma￾terial, our subject is an experience-intensive one, and by definition students are short on that commodity. There are many moments in organic chemistry when it is important to take stock of where we are. Summary sections have been incorporated into every chapter. Here the narrative is broken and the reader is brought up to date on the important points of the previous topic.These summaries serve as excellent “reminder and review” sections when a student is studying for an exam. Each chapter ends with a summary of New Concepts, Key Terms, new Reactions, Mechanisms, and Tools, new Syntheses, and Common Errors. These sections recapitulate and reinforce the material of the chapter, and serve as excellent study tools. We incorporate unsolved problems in two ways. There are many such problems scattered throughout the text and more problems, of all degrees of difficulty, are found at the end of each chapter. They range from drill exercises and simple examples, designed to emphasize important skills and illustrate techniques, to sophisticated, challenging problems. In those last cases, we are careful to provide hints and refer￾ences to material useful for the solution. All these problems are solved in the Study Guide, which does much more than provide a bare-bones answer. It, along with the new Problem Solving sections in the fourth edition, tries to show students prob￾lem-solving techniques that will help them solve future problems. There are also many solved problems in the text, each designed to reinforce a point just made. The fourth edition contains many new problems including ones that require the use of the Organic Reactions Animations software. Highlights of the Content and Organizational Changes in the Fourth Edition The fourth edition has: • A much more complete discussion of resonance in Chapter 1. This change is in response to a request by reviewers who felt this central theme should be presented as early as possible. We agree. Understanding resonance structures is critical, and early coverage provides a strong foundation. The student will have a chance to review the topic in Chapter 9. • A reorganization of Chapter 15. The new outline emphasizes important topics in NMR spectroscopy. Also, the chapter was modified so that it is even more movable than it was in the third edition, in case the instructor wants to present spectroscopy early in the first semester. We believe spectroscopy is a topic that should be taught early. Students can use the tools (UV, IR, NMR, MS) to help understand symme￾try, resonance, electronegativity, aromaticity, acidity, and reactivity of molecules. Spectroscopy is an important tool to link structure and activity. • Enolates discussed as a single topic in Chapter 19. Earlier editions of this text had the enolate topic covered in two chapters separated by a chapter on carboxylic acids. Because enolates of aldehydes, ketones, esters, and carboxylic acids all share similar PREFACE TO THE FOURTH EDITION xxv PROBLEM SOLVING Whenever you see the word “rate” in a problem, or when you see words such as “faster” that talk about rates, you are very likely to have to answer the question by drawing the transition state for the reaction. Remember that the rate of a reaction is determined by ΔG‡ , the energy difference between starting material and the transition state, and not by the energy difference between starting material and product. You need a pull-down menu that says, “Think about the transition state” when the word “rate” appears in a problem

xxvi PREFACE TO THE FOURTH EDITION reactions,we have combined them into one chapter.It is the chemistry of carban- ions formed by deprotonating the carbon alpha to a carbonyl that sews this chapter together.Students will benefit from this unified approach to enolate chemistry. New structures and topics in the carbohydrate chapter,Chapter 22.This chapter was rewritten in an attempt to provide more current carbohydrate material.Many instructors do not cover carbohydrates in their organic chemistry course,but those who do will find both the historical Fischer proof and modern synthetic methods presented in this chapter.We have drawn most of the carbohydrates as chair struc- tures so that students can recognize and remember why glucose is the most com- mon carbohydrate. .Special Topics in most chapters (except Chapters 7,20,21,and 23).This material deals with logical extensions and applications of related subjects.Instructors who choose to move through the chapters more quickly may opt to leave these sections out of lecture material.We hope students will read the Special Topic sections.The material is provided because we believe it is important,but we recognize that it is not critical. .A substantially increased use of the terms electropbile and nucleopbile throughout the text.There is a unifying theme that the interaction between Lewis acids (elec- trophiles)and Lewis bases (nucleophiles)in organic chemistry is stabilizing.In orbital terms,that statement simply means that the interaction between a filled and empty orbital is stabilizing.The text has a focus on this principle and the frequent use of these terms will help direct the student to see their significance. More end-of-chapter problems.Over 100 new problems have been added in this edition.The added problems are not the mind-numbing sort;these are practice problems that will give the student more experience and confidence with the sub- ject.Organic Reaction Animations (ORA)problems have also been added.These questions will help the student connect the ORA visualizations with the principles being discussed in the chapter. Overall Organization To understand atoms and molecules one must first think sensibly about electrons, and for that we need to explore a bit of what quantum mechanics tells us.That does not mean we will all have to become mathematicians.Far from it.Our discussion here will be purely qualitative,since we need only grasp qualitatively what the math- ematicians have to say to us.Qualitative molecular orbital theory is not too compli- cated a subject for students,and requires no mathematics.Yet,this simple theory is amazingly powerful in its ability to rationalize and,especially,to predict structure and reactivity.The abbreviated tutorial in Chapter 1 on qualitative applications of molecular orbital theory is likely to be new to students.This material is important, as it enables us to emphasize explanations throughout the rest of the book.Not only are traditional subjects such as aromaticity and conjugation(Chapters 12-14)more accessible with the background of Chapter 1,but explanations for the essential,build- ing-block reactions of organic chemistry (Chapters 7 and 9,for example)become possible.There is,after all,no essential difference between the classic statement "Lewis acids react with Lewis bases"and the idea that the interaction of a filled and empty orbital is stabilizing.The latter formulation allows all sorts of seemingly dis- parate reactions to be gathered together-unified-in a very useful way.(For exam- ple,a hydride shift and the SN1 reaction become partners in a unified theory rather than two wildly different reactions that must be memorized in all their detail)

reactions, we have combined them into one chapter. It is the chemistry of carban￾ions formed by deprotonating the carbon alpha to a carbonyl that sews this chapter together. Students will benefit from this unified approach to enolate chemistry. • New structures and topics in the carbohydrate chapter, Chapter 22. This chapter was rewritten in an attempt to provide more current carbohydrate material. Many instructors do not cover carbohydrates in their organic chemistry course, but those who do will find both the historical Fischer proof and modern synthetic methods presented in this chapter. We have drawn most of the carbohydrates as chair struc￾tures so that students can recognize and remember why glucose is the most com￾mon carbohydrate. • Special Topics in most chapters (except Chapters 7, 20, 21, and 23). This material deals with logical extensions and applications of related subjects. Instructors who choose to move through the chapters more quickly may opt to leave these sections out of lecture material. We hope students will read the Special Topic sections. The material is provided because we believe it is important, but we recognize that it is not critical. • A substantially increased use of the terms electrophile and nucleophile throughout the text. There is a unifying theme that the interaction between Lewis acids (elec￾trophiles) and Lewis bases (nucleophiles) in organic chemistry is stabilizing. In orbital terms, that statement simply means that the interaction between a filled and empty orbital is stabilizing. The text has a focus on this principle and the frequent use of these terms will help direct the student to see their significance. • More end-of-chapter problems. Over 100 new problems have been added in this edition. The added problems are not the mind-numbing sort; these are practice problems that will give the student more experience and confidence with the sub￾ject. Organic Reaction Animations (ORA) problems have also been added. These questions will help the student connect the ORA visualizations with the principles being discussed in the chapter. Overall Organization To understand atoms and molecules one must first think sensibly about electrons, and for that we need to explore a bit of what quantum mechanics tells us.That does not mean we will all have to become mathematicians. Far from it. Our discussion here will be purely qualitative, since we need only grasp qualitatively what the math￾ematicians have to say to us. Qualitative molecular orbital theory is not too compli￾cated a subject for students, and requires no mathematics. Yet, this simple theory is amazingly powerful in its ability to rationalize and, especially, to predict structure and reactivity. The abbreviated tutorial in Chapter 1 on qualitative applications of molecular orbital theory is likely to be new to students. This material is important, as it enables us to emphasize explanations throughout the rest of the book. Not only are traditional subjects such as aromaticity and conjugation (Chapters 12–14) more accessible with the background of Chapter 1, but explanations for the essential, build￾ing-block reactions of organic chemistry (Chapters 7 and 9, for example) become possible. There is, after all, no essential difference between the classic statement “Lewis acids react with Lewis bases” and the idea that the interaction of a filled and empty orbital is stabilizing. The latter formulation allows all sorts of seemingly dis￾parate reactions to be gathered together—unified—in a very useful way. (For exam￾ple, a hydride shift and the SN1 reaction become partners in a unified theory rather than two wildly different reactions that must be memorized in all their detail.) xxvi PREFACE TO THE FOURTH EDITION

PREFACE TO THE FOURTH EDITION xxvii The language that makes both the macro scale and the micro scale accessible to us is mathematics.Although we need not do the mathematical operations ourselves, we do need to appreciate some of the things that quantum mechanics has to say to us.Chapter 1 also focuses strongly on Lewis structures-pictorial representations of atoms and ions.The ability to write good Lewis structures easily and to deter- mine the locations of charges in molecules with ease is an essential skill.This skill is part of the language of chemistry and will be as important in Chapter 23 as it is in Chapter 1. After the introductory chapter comes a sequence of four chapters devoted large- ly to aspects of structure(Chapters 2-5).Here the details of the archetypal struc- tures of organic chemistry are introduced.Hybridization appears,and the wonderful three-dimensionality of the subject begins to grow in.Some functional groups are introduced,and stereochemistry is dealt with in depth.A particularly vexing and fun- damental question concerns what makes two atoms or molecules the same or dif- ferent.The fourth edition includes a preview of NMR spectroscopy in Chapter 2. This section is not detailed-it is only an introduction-but it allows a real discus- sion of that elusive question of"difference."It also allows reinforcement through a series of new problems introduced throughout the first half of the book. In Chapter 3,the addition of HX molecules to alkenes allows an introduction to synthesis,as well as a discussion of selectivity,catalysis,and reaction mechanism in general. After the series of"structure"chapters comes Chapter 6 on alcohols,amines, halides,and the properties of solvents.This chapter functions as a lead in to a dis- cussion of several building-block reactions,the Sv2,SN1,E2,and E1 reactions. Chapter 7 is one of the key chapters,and the reactions discussed here-substi- tution and elimination-serve as reference points throughout the book;they are fun- damental reactions to which we return over and over in later chapters in order to make analogies. Once we have these basic reference reactions under control,a general discussion of the role of energetics-kinetics and thermodynamics-becomes appropriate (Chapter 8).Chapters 9 and 10 introduce other building-block reactions,and other functional groups,in the context of an expansion of the earlier discussion of addi- tion reactions in Chapter 3.Even at these early stages we introduce the biological applications of organic chemistry.For example,in the chapters devoted to the struc- ture of alkanes,and,especially,alkenes,biorelevant examples appear.These do not obscure the essential information of the chapters,however.They are kept as exam- ples,potential extensions,and applications of what we have learned at this point. Later on in the book their role is expanded,with whole chapters(Chapters 22 and 23)devoted to biological topics. The basic reactions of the middle chapters(Chapters 7-14)provide a founda- tion for the chemistry of carbonyl compounds,the subject of a series of chapters in the second half of the book (Chapters 16-19). Chapter 15,set in the midst of this run of chapters,is devoted to spectroscopy. Sections of earlier chapters have already dealt with parts of this subject in an intro- ductory way (Chapter 2 for NMR,Chapter 12 for UV/vis).So,in order to allow flexible usage of this chapter,we have tried to make this chapter freestanding. To make an analogy to the study of a language,in the first sequence of reaction chapters(Chapters 7,9,and 10)we write sentences constructed from the vocabu- lary and grammar developed in the early,structural chapters.We will go on in later chapters in the book to more complicated mechanisms and molecules,and to write

The language that makes both the macro scale and the micro scale accessible to us is mathematics. Although we need not do the mathematical operations ourselves, we do need to appreciate some of the things that quantum mechanics has to say to us. Chapter 1 also focuses strongly on Lewis structures—pictorial representations of atoms and ions. The ability to write good Lewis structures easily and to deter￾mine the locations of charges in molecules with ease is an essential skill. This skill is part of the language of chemistry and will be as important in Chapter 23 as it is in Chapter 1. After the introductory chapter comes a sequence of four chapters devoted large￾ly to aspects of structure (Chapters 2–5). Here the details of the archetypal struc￾tures of organic chemistry are introduced. Hybridization appears, and the wonderful three-dimensionality of the subject begins to grow in. Some functional groups are introduced, and stereochemistry is dealt with in depth. A particularly vexing and fun￾damental question concerns what makes two atoms or molecules the same or dif￾ferent. The fourth edition includes a preview of NMR spectroscopy in Chapter 2. This section is not detailed—it is only an introduction—but it allows a real discus￾sion of that elusive question of “difference.” It also allows reinforcement through a series of new problems introduced throughout the first half of the book. In Chapter 3, the addition of HX molecules to alkenes allows an introduction to synthesis, as well as a discussion of selectivity, catalysis, and reaction mechanism in general. After the series of “structure” chapters comes Chapter 6 on alcohols, amines, halides, and the properties of solvents. This chapter functions as a lead in to a dis￾cussion of several building-block reactions, the SN2, SN1, E2, and E1 reactions. Chapter 7 is one of the key chapters, and the reactions discussed here—substi￾tution and elimination—serve as reference points throughout the book; they are fun￾damental reactions to which we return over and over in later chapters in order to make analogies. Once we have these basic reference reactions under control, a general discussion of the role of energetics—kinetics and thermodynamics—becomes appropriate (Chapter 8). Chapters 9 and 10 introduce other building-block reactions, and other functional groups, in the context of an expansion of the earlier discussion of addi￾tion reactions in Chapter 3. Even at these early stages we introduce the biological applications of organic chemistry. For example, in the chapters devoted to the struc￾ture of alkanes, and, especially, alkenes, biorelevant examples appear. These do not obscure the essential information of the chapters, however. They are kept as exam￾ples, potential extensions, and applications of what we have learned at this point. Later on in the book their role is expanded, with whole chapters (Chapters 22 and 23) devoted to biological topics. The basic reactions of the middle chapters (Chapters 7–14) provide a founda￾tion for the chemistry of carbonyl compounds, the subject of a series of chapters in the second half of the book (Chapters 16–19). Chapter 15, set in the midst of this run of chapters, is devoted to spectroscopy. Sections of earlier chapters have already dealt with parts of this subject in an intro￾ductory way (Chapter 2 for NMR, Chapter 12 for UV/vis). So, in order to allow flexible usage of this chapter, we have tried to make this chapter freestanding. To make an analogy to the study of a language, in the first sequence of reaction chapters (Chapters 7, 9, and 10) we write sentences constructed from the vocabu￾lary and grammar developed in the early, structural chapters. We will go on in later chapters in the book to more complicated mechanisms and molecules, and to write PREFACE TO THE FOURTH EDITION xxvii

xxviii PREFACE TO THE FOURTH EDITION whole paragraphs and even short essays in organic chemistry.Some of those essays are contained in the Special Topics chapters toward the end of the book(Chapters 20-23)in which biological chemistry and physical-organic chemistry are further explored with the material of the early chapters as a foundation. Flexibility.There is no consensus on the precise order in which to take up many subjects in organic chemistry.This book makes different decisions possible.For example,as already pointed out,the spectroscopy chapter is largely freestanding. Traditionally,it comes where it is here,roughly at the midpoint of the book.But cogent arguments can be made that spectroscopy should be introduced earlier,and that is possible,if one is willing to pay the price of delaying the serious discussion of chemical reactions one more chapter. The last few chapters explicitly constitute a series of Special Topics.No one real- ly hopes to finish everything in an organic textbook in one year,and this book pro- vides a number of choices.One might emphasize biological aspects of our science, for example,and Chapters 22 and 23 provide an opportunity to do this.Alternatively, a more physical approach would see the exciting chemistry of Chapters 20 and 21 as more appropriate. Instructor Resources PowerPoint slides,available at wwnorton.com/nrl.Both lecture slides and slides containing textbook art are available for download from the instructor site.Lecture slides include questions for classroom response systems(also known as clickers). Transparency set,with approximately 150 key figures from the text. Test Bank(Tim Minger,Mesa Community College).New to the fourth edition, the Test Bank contains 1,150 questions from which to choose.Questions are organ- ized by chapter section,and each question is ranked by difficulty and type.The Test Bank is available as a printed book,in Word RTF,in PDF,and in ExamView Assessment Suite. Student Resources Study Guide/Solutions Manual (Maitland Jones,Jr.,New York University;Henry L. Gingrich,Princeton University;Steven A.Fleming,Temple University).Written by the textbook authors,this guide provides students with fully worked solutions to all unworked problems that appear in the text.In addition to the solutions presented for each specific problem,the authors present good problem-solving strategies for solving organic chemistry problems in general. StudySpace,available at wwnorton.com/studyspace.This free and open Web site is available to all students.StudySpace includes more than 350 interactive,3-D WEB3D molecules from the text (formerly hosted on Norton's Orgo3D Web site).These structures were made in Chem3D and can be manipulated in space and viewed in several ways(ball-and-stick,space-filling,etc.).In addition,there is a short writeup and usually a few questions (and answers!)for most of the molecules. StudySpace will house two review features from the text:Essential Skills and Details and Convention Alerts.The site will also provide links to the ebook and SmartWork. SmartWork:an online tutorial and homework program for organic chemistry, available at wwnorton.com/smartwork.SmartWork is the most intuitive online tutorial and homework-management system available for organic chemistry.Powerful

whole paragraphs and even short essays in organic chemistry. Some of those essays are contained in the Special Topics chapters toward the end of the book (Chapters 20–23) in which biological chemistry and physical-organic chemistry are further explored with the material of the early chapters as a foundation. Flexibility. There is no consensus on the precise order in which to take up many subjects in organic chemistry. This book makes different decisions possible. For example, as already pointed out, the spectroscopy chapter is largely freestanding. Traditionally, it comes where it is here, roughly at the midpoint of the book. But cogent arguments can be made that spectroscopy should be introduced earlier, and that is possible, if one is willing to pay the price of delaying the serious discussion of chemical reactions one more chapter. The last few chapters explicitly constitute a series of Special Topics. No one real￾ly hopes to finish everything in an organic textbook in one year, and this book pro￾vides a number of choices. One might emphasize biological aspects of our science, for example, and Chapters 22 and 23 provide an opportunity to do this. Alternatively, a more physical approach would see the exciting chemistry of Chapters 20 and 21 as more appropriate. Instructor Resources • PowerPoint slides, available at wwnorton.com/nrl. Both lecture slides and slides containing textbook art are available for download from the instructor site. Lecture slides include questions for classroom response systems (also known as clickers). • Transparency set, with approximately 150 key figures from the text. • Test Bank (Tim Minger, Mesa Community College). New to the fourth edition, the Test Bank contains 1,150 questions from which to choose. Questions are organ￾ized by chapter section, and each question is ranked by difficulty and type.The Test Bank is available as a printed book, in Word RTF, in PDF, and in ExamView Assessment Suite. Student Resources • Study Guide/Solutions Manual (Maitland Jones, Jr., New York University; Henry L. Gingrich, Princeton University; Steven A. Fleming,Temple University). Written by the textbook authors, this guide provides students with fully worked solutions to all unworked problems that appear in the text. In addition to the solutions presented for each specific problem, the authors present good problem-solving strategies for solving organic chemistry problems in general. • StudySpace, available at wwnorton.com/studyspace. This free and open Web site is available to all students. StudySpace includes more than 350 interactive, 3-D molecules from the text (formerly hosted on Norton’s Orgo3D Web site). These structures were made in Chem3D and can be manipulated in space and viewed in several ways (ball-and-stick, space-filling, etc.). In addition, there is a short writeup and usually a few questions (and answers!) for most of the molecules. StudySpace will house two review features from the text: Essential Skills and Details and Convention Alerts. The site will also provide links to the ebook and SmartWork. • SmartWork: an online tutorial and homework program for organic chemistry, available at wwnorton.com/smartwork. SmartWork is the most intuitive online tutorial and homework-management system available for organic chemistry. Powerful xxviii PREFACE TO THE FOURTH EDITION WEB 3D