《有机化学》课程教学资源（参考书籍）Organic Chemistry（7th Edition）Prentice Hall（2009, L.G. Wade, Jr. Whitman College）.pdf_P21-P25

xxiv Preface I've continued the gradual transition to the newer IUPAC names with the revised locations of numbers, such as in hexa-1,3-diene instead of 1,3-hexadiene. I've also completed the transition from kcal to kJ as the primary energy units, since kJ units are used in all general chemistry texts at this time. I've added several sections to recent editions to cover new material or material of current interest. Chapter 4: A section on free-radical inhibitors was added to show students how some of the common inhibitors break the free-radical chain reaction, and their importance in chemistry and biochemistry. Chapter 5: Using the Mislow and Siegel definition (1. Am. Chern. Soc. 1984, 106, 3319), I introduce the popular (but often incorrectly defined) term stereocenter and explain the differences between this term and the IUPAC terms chirality center and asymmetric carbon atom (or chiral carbon atom). The term stereocenter is much broader than the more precise term asymmetric carbon atom, and it assumes that one already knows the stereochemical properties of the molecule (to know which bonds will give rise to stereoisomers upon their interchange). The casual use of the broad term stereocenter where a more precise term is required often results in logical fallacies (1. Chern. Educ. 2006, 83, 1793 ). Therefore, I have continued to encourage students to identify the (immediately apparent) asymmetric carbon atoms to use as tools in examining a molecule to determine its stereochemistry. Chapter 8: The Nobel Prize-winning asymmetric reduction work by Noyori and Knowles is discussed, together with its implications for enantioselective drug synthesis. Another new section has been added covering the mechanism and synthetic uses of olefin metathesis, highlighting the work by Chauvin, Grubbs, and Schrock that recently won the Nobel Prize. Chapter 12: Fourier-transform IR spectroscopy is discussed, together with the reasons why this technique gives improved sensitivity and resolution over the dispersive method. Chapter 13: The NMR spectra have been converted to high-field (300 MHz) spectra from the excellent Aldrich collection. The expansion boxes have been refined and clarified to make sure that the individual splittings are visible. The DEPT technique has been expanded and used in more of the problems. Chapter 14: The Nobel Prize-winning Sharpless asymmetric epoxidation is discussed, together with the factors that selectively enhance the formation of one enantiomer of the product. Chapter 16: A section has been added that discusses the aromaticity of Fullerenes and their relationship to other allotropes of carbon. Chapter 24: A section has been added that discusses prions: proteins which are thought to be infectious because of misfolding, resulting in clumping and formation of plaques. This topic relates the topic at hand (protein conformations) directly to the ongoing concern about mad cow disease. 3. Electrostatic Potential Maps. Electrostatic potential maps are used in cases where they might help students to visualize the charge distribution of a species in a way that helps to explain the electrophilic or nucleophilic nature of a compound. In introducing EPMs, I've emphasized their qualitative nature without stressing their mathematical derivation. As a result, I've explained and used EPMs much like they are introduced in the general chemistry textbooks. Several new EPMs have been added in the seventh edition. The entire book has been edited, with many sections reorganized and rewritten to enhance clarity. As in the first edition, each new topic is introduced carefully and explained thoroughly. Many introductory sections have been rewritten to update them and make them more approachable for students. Whenever possible, illustrations have been added or modified to help students visualize the physical concepts

The emphasis continues to be on chemical reactivity. Chemical reactions are introduced as soon as possible, and each functional group is considered in view of its reactivity toward electrophiles, nucleophiles, oxidants, reductants, and other reagents. "Electron-pushing" mechanisms are stressed throughout as a means of explaining and predicting this reactivity. Structural concepts such as stereochemistry and spectroscopy are thoroughly treated as useful techniques that enhance the fundamental study of chemical reactivity. Organization This book maintains the traditional organization that concentrates on one functional group at a time while comparing and contrasting the reactivity of different functional groups. Reactions are emphasized, beginning with Lewis acid-base reactions in Chapter 1, continuing with thermodynamics and kinetics in Chapter 4, and covering most of the important substitution, addition, and elimination reactions in the three chapters following stereochemistry. Spectroscopic techniques (IR, MS, and NMR) are covered in Chapters 12 and 13, so that they can be included in the first semester if desired. This early coverage is needed to allow effective use of spectroscopy in the laboratory. Still, a large amount of organic chemistry has been covered before this digression into structure determination. The principles of spectroscopy are practiced and reinforced in later chapters, where the characteristic spectral features of each functional group are summarized and reinforced by practice problems. Key Features FLEXIBILITY OF COVERAGE No two instructors teach organic chemistry exactly the same way. This book covers all the fundamental topics in detail, building each new concept on those that come before. Many topics may be given more or less emphasis at the discretion of the instructor. Examples of these topics are 13C NMR spectroscopy, ultraviolet spectroscopy, conservation of orbital symmetry, amino acids and proteins, nucleic acids, and the special topics chapters, lipids and synthetic polymers. Another area of flexibility is in the problems. The wide-ranging problem sets review the material from several viewpoints, and more study problems are provided than most students are able to complete. This large variety allows the instructor to select the most appropriate problems for the individual course. UP-TO-DATE TREATMENT In addition to the classical reactions, this book covers many techniques and reactions that have more recently gained wide use among practicing chemists. Molecular-orbital theory is introduced early and used to explain electronic effects in conjugated and aromatic systems, pericyclic reactions, and ultraviolet spectroscopy. Carbon-13 NMR spectroscopy is treated as the routine tool it has become in most research laboratories, and the DEPT technique is introduced in this edition. Many of the newer synthetic techniques are also included, such as asymmetric hydrogenation and epoxidation, use of sodium triacetoxyborohydride, Birch reduction, Swern oxidations, alkylation of 1,3-dithianes, olefin metathesis, and oxidations using pyridinium chlorochromate. REACTION MECHANISMS Reaction mechanisms are important in all areas of organic chemistry, but they are difficult for many students. Students fall into the trap of memorizing a mechanism while not understanding why it proceeds as it does. This book stresses the principles used to predict mechanisms. Problem-solving sections develop basic techniques for approaching Preface xxv

xxvi Preface mechanism problems, and they work to minimize rote memorization. These techniques emphasize deciding whether the reaction is acidic, basic, or free radical in nature, then breaking it down into Lewis acid-base interactions and using "electron pushing arrows" to illustrate these individual steps. Important mechanisms are highlighted by placing them in the Mechanism and Key Mechanism boxes. INTRODUCTION TO MECHANISMS USING FREE-RADICAL HALOGENATION The advantages and disadvantages of using free-radical halogenation to introduce reaction mechanisms have been debated for many years. The principal objection to freeradical halogenation is that it is not a useful synthetic reaction. But useful reactions such as nucleophilic substitution and additions to alkenes are complicated by participation of the solvent and other effects. Gas-phase free-radical halogenation allows a clearer treatment of kinetics and thermodynamics, as long as its disadvantages as a synthetic reaction are discussed and students are aware of the limitations. ORGANIC SYNTHESIS Organic synthesis is stressed throughout this book, with progressive discussions of the process involved in developing a synthesis. Retrosynthetic analysis is emphasized, and the student learns to work backward from the target compound and forward from the starting materials to find a common intermediate. Typical yields have been provided for many synthetic reactions, although I hope students will not misuse these numbers. Too often students consider the yield of a reaction to be a fixed characteristic just as the melting point of a compound is fixed. In practice, many factors affect product yields, and literature values for apparently similar reactions often differ by a factor of 2 or more. The yields given in this book are typical yields that a good student with excellent technique might obtain. SPECTROSCOPY Spectroscopy is one of the most important tools of the organic chemist. This book develops the theory for each type of spectroscopy and then discusses the characteristic spectral features. The most useful and dependable characteristics are summarized into a small number of rules of thumb that allow the student to interpret most spectra without looking up or memorizing large tables of data. For reference use, extensive tables of NMR and IR data and a more complete version of the Woodward-Fieser rules for UV are provided as appendices. This approach is particularly effective with IR and NMR spectroscopy, and with mass spectrometry. Practical rules are given to help students see what information is available in the spectrum and what spectral characteristics usually correspond to what structural features. Sample problems show how the information from various spectra is combined to propose a structure. The emphasis is on helping students develop an intuitive feel for using spectroscopy to solve structural problems. NOMENCLATURE IUPAC nomenclature is stressed throughout the book, but common nomenclature is also discussed and used to develop students' familiarity. Teaching only the IUPAC nomenclature might be justifiable in theory, but such an approach would handicap students in their further study and use of the literature. Much of the literature of chemistry, biology, and medicine uses common names such as methyl ethyl ketone, isovaleric acid, methyl tert-butyl ether, y-aminobutyric acid, and c:-caprolactam. This book emphasizes why systematic nomenclature is often preferred, yet it encourages familiarity with common names as well. I've enjoyed working on this new edition, and I hope that it is an improved finetuning of the sixth edition. I've tried to make this book as error-free as possible, but I'm sure some errors have slipped by. If you find errors, or have suggestions about how the book might be made better, please let me know (L. G. Wade, Whitman College

Walla Walla, WA 99362; e-mail: wadelg@whitman.edu). Errors can be fixed quickly in the next printing. I've already started a file of possible changes and improvements for the eighth edition, and I hope many of the current users will contribute suggestions to this file. I hope this book makes your job easier and helps more of your students to succeed. That's the most important reason why I wrote it. INSTRUCTOR RESOURCES Instructor Resource on CD/DVD (0-32-159872-5) This lecture resource is prepared by Rizalia Klausmeyer of Bay lor University and Christine Hermann of Radford University. This resource provides an integrated collection of resources to help you make efficient and effective use of your time. This CD/DVD features most art from the text including figures and tables in PDF format for high-resolution printing, as well as four pre-built PowerPoint presentations. The first contains images embedded within the slides, the second contains worked examples in progressive reveal format, the third contains Clicker "CRS" questions and the final PowerPoint presentation is a Lecture outline. This CD/DVD also contains the TestGen, a computerized version of the Test Item File that enables professors to create and tailor exams to their needs. ACE Organic Chemistry On-Line Homework System Pearson Prentice Hall, in conjunction with Robert B. Grossman and Raphael A. Finkel and a team of programmers at the University of Kentucky, has developed a homework system for organic chemistry that can finally support the types of problems assigned in organic chemistry. The homework system contains hundreds of organic chemistry structure-drawing problems, allows students to draw structures, recognizes correct and incorrect answers, and provides structure-specific feedback. This drawing activity with immediate feedback results in a better learning experience for students. The homework system also grades student responses automatically and stores their activity in a gradebook, providing you a better way to track student learning while saving you time. Please contact your local Prentice Hall representative for more information. Transparency Set (0-32-159869-5) This package comprises 275 four-color acetates of the most useful images, computer art, and line drawings from the text. The Transparency Pack is available at no charge to adopters of Organic Chemistry, Seventh Edition. Test Item File (0-32-159868-7) by Gary Hollis of Roanoke College; Don Davies of Weber State University; and Todd Johnson of Weber State University. This is a printed version of all questions in the TestGen software found on the Instructor Resource on CD/DVD. The new Seventh Edition contains over 2600 questions. BlackBoard and WebCT: Practice and assessment materials are available upon request in these course management platforms. Acknowledgments I am pleased to thank the many talented people who helped with this revision. More than anyone else, Jan Simek, author of the Solutions Manual, has consistently provided me with excellent advice and sound judgment through several editions of this book. In this edition, Jan provided input on all of the chapter revisions, and helped with the writing of the new section on olefin metathesis. He also co-authored most of the new problems and all of the Answers to Selected Problems. Particular thanks are also due to John Murdzek and Ray Mullaney, who both made thousands of useful suggestions throughout the writing and revision process, and who helped to shape this new edition. I would like to thank the reviewers for their valuable insight and commentary. Although I did not adopt all their suggestions, most of them were helpful and contributed to the quality of the final product. Preface xxvii

xxviii Preface Seventh Edition Prescriptive Reviewers Steven Graham Fathi Halaweish Julius Harp Christine Hermann Kathy Hess St. John's University, Jamaica Jung-MoAhn Arthur J. Ashe Merritt B. Andrus David Brown Kristen Meisenheimer Stephen A Miller Guillermo Moyna Anthony J. Pearson Stanley Raucher David Son Joseph B. Wachter University of Texas at Dallas University of Michigan Brigham Young University St. John's University Cal Polytechnic at San Luis Obispo University of Florida University of the Sciences in Philadelphia Case Western Reserve University University of Washington Southern Methodist University Michigan State University Steve Holmgren Angela King Vera Kolb Paul Kropp Scott Lewis Guigen Li Helena Malinakova MarkMascal South Dakota State University North Carolina A&T University Radford University Cypress College Montana State University Wake Forest University University of Wisconsin, Parkside University of North Carolina, Chapel Hill James Madison University Texas Tech University University of Kansas Sixth Edition Prescriptive Reviewers John Masnovi University of California, Davis Cleveland State University Bill Baker Barry Coddens Barbara Colonna Chris Gorman Geneive Henry William Jenks Przemyslaw Maslak Rabi Musah Allan Pinhas Suzanne Ruder Maria de Graca Vicente University of South Florida Northwestern University University of Miami North Carolina State University Susquehanna University Iowa State University Pennsylvania State University University at Albany University of Cincinnati Virginia Commonwealth University Louisiana State University John McBride Martin McClinton James R. McKee Gary Miracle Gholam Mirafzal Tom Mitzel David Modarelli Andrew Morehead Richard Morrison Thomas Nalli Michael Nee Northwest Vista College Brevard Community College University of the Sciences in Philadelphia Texas Tech University Drake University Trinity College University of Akron East Carolina University University of Georgia Winona State University Sixth Edition Manuscript Reviewers Mark Niemczyk Glenn Nomura Patrick O'Connor Cyril Parkanyi Anthony Pearson John Penn University of California, Berkeley Wheaton College Georgia Perimeter College David Alonso Rutgers University Dan Becker John Berger Bob Bly Mary Boyd Hindy Bronstein Philip Brown Christine Brzezowski Patrick Buick David Cantillo Dee Ann Casteel Amber Charlebois Cai Chengzhi Jamie Lee Cohen Richard Conley Robert Crow William Donaldson Aouad Emmanuel Malcolm Forbes Anne Gaquere Rainer Glaser Andrews University Loyola University Montclair State University University of South Carolina Loyola University, Chicago Fordham College at Lincoln Center North Carolina State University University of Alberta Florida Atlantic University Hillsborough Community College Bucknell University William Paterson University University of Houston Pace University Middlesex County College St. Louis College of Pharmacy Marquette University Rutgers University, Newark Campus University of North Carolina, Chapel Hill State University of West Georgia University of Missouri, Columbia James Poole Owen Priest John Rainier Kirk Schanze David Shultz Joseph Sloop Luise Strange John Struss Joseph Tufariello Kent Voelkner Dan Von Riesen Sheild Wallace Lisa Whalen Florida Atlantic University Case Western Reserve University West Virginia University Ball State University Northwestern University University of Utah University of Florida North Carolina State University United States Military Academy Georgia Perimeter College University of Tampa University at Buffalo Lake Superior State College Roger Williams University Albuquerque Technical Vocational Institute University of New Mexico Sixth Edition Accuracy Reviewers Thomas Nalli Susan Scheible Winona State University University of Colorado at Denver Finally, I want to thank the people at Prentice Hall, whose dedication and flexibility contributed to the completion of this project. Assistant Editor Carol DuPont and Editor in Chief Nicole Folchetti kept the project moving, ensured the needed resources were available, and made many useful comments and suggestions. Production Editor Rebecca Dunn kept the production process organized, on track, and on schedule. It has been a pleasure working with all these thoroughly professional and competent people. L. G. Wade, Jr. Walla Walla, Washington