《有机化学》课程教学资源（参考书籍）Organic Chemistry With Biological Applications, 2nd Edition -Brooks Cole（2010, John McMurry, Cornell University）

PREFACE xix ()is uni ain clas coverage.The i ates w h ach ajo mechanipath fo owing an c chemistry.Finally.the book ends with a c apterdevotel to natural products and their biosynthesis. Content Changes in the Second Edition Text content has been revised substantially for this second edition as a result of user feedback.Consequently.the text covers most of the standard topics found in typical organic courses yet still retains an emphasis on biological reactions and molecules perhans the most noticeable change is that the book is now titled Organic Chemistry with Biological Applications to emphasize that it is,above all,written for the standard organic chemistry course found in colleges and universities everywhere. Within the text itself,a particularly important change is that the chapter on chirality and stereochemistry at tetrahedral centers,a topic crucial to understanding biological chemistry,has been moved forward to Chapter 4 from its previous placement in Chapter 9.In addition,the chapter on organo- halides has been moved from Chapter 10 to Chapter 12,thereby placing spec- troscopy earlier(Chapters 10 and 11). Other Changes and Newly Added Content Alkene ozonolysis and diol cleavage-added in Section 8.8 Addition of carbenes to alkenes-added in Section 8.9 The Diels-Alder cycloaddition reaction-added in Section 8.14 Acetvlide alkvlations-added in Section 8.15 Aromatic ions-added in Section 9.4 Nucleophilic aromatic substitution-added in Section 9.9 Aromatic hydrogenation-added in Section 9.10 Allvlic bromination of alkenes-added in section 12.2 Dess-Martin oxidation of alcohols-added in Section 13.5 Protection of alcohols as silyl ethers-added in Section 13.6 Claisen rearrangement-added in Section 13.10 Protection of ketones and aldehydes as acetals-added in Section 14.8 。 Coniugate addition of diorganocuprates to enones-added in section 14.11 Grignard reaction of nitriles-added in Section 15. Reaction of diorganocuprates with acid halides-added in Section 16.4 Alpha bromination of carboxylic acids-added in Section 17.3 Amino acid metabolism-simplified coverage,Section 20.4 Amino acid biosynthesis-simplified coverage,Section 20.5 Final comments on metabolism-added in Section 23.10 Nucleotide metabolism-simplified coverage,Section 24.9

preface xix (see Section 8.5, page 261). The third group of chapters (19–25) is unique to this text in their depth of coverage. These chapters deal exclusively with the main classes of biomolecules—amino acids and proteins, carbohydrates, lip￾ids, and nucleic acids—and show how thoroughly organic chemistry perme￾ates biological chemistry. Following an introduction to each class, major metabolic pathways for that class are discussed from the perspective of mechanistic organic chemistry. Finally, the book ends with a chapter devoted to natural products and their biosynthesis. Content Changes in the Second Edition Text content has been revised substantially for this second edition as a result of user feedback. Consequently, the text covers most of the standard topics found in typical organic courses yet still retains an emphasis on biological reactions and molecules. Perhaps the most noticeable change is that the book is now titled Organic Chemistry with Biological Applications to emphasize that it is, above all, written for the standard organic chemistry course found in colleges and universities everywhere. Within the text itself, a particularly important change is that the chapter on chirality and stereochemistry at tetrahedral centers, a topic crucial to understanding biological chemistry, has been moved forward to Chapter 4 from its previous placement in Chapter 9. In addition, the chapter on organo￾halides has been moved from Chapter 10 to Chapter 12, thereby placing spec￾troscopy earlier (Chapters 10 and 11). Other Changes and Newly Added Content • Alkene ozonolysis and diol cleavage—added in Section 8.8 • Addition of carbenes to alkenes—added in Section 8.9 • The Diels–Alder cycloaddition reaction—added in Section 8.14 • Acetylide alkylations—added in Section 8.15 • Aromatic ions—added in Section 9.4 • Nucleophilic aromatic substitution—added in Section 9.9 • Aromatic hydrogenation—added in Section 9.10 • Allylic bromination of alkenes—added in Section 12.2 • Dess–Martin oxidation of alcohols—added in Section 13.5 • Protection of alcohols as silyl ethers—added in Section 13.6 • Claisen rearrangement—added in Section 13.10 • Protection of ketones and aldehydes as acetals—added in Section 14.8 • Conjugate addition of diorganocuprates to enones—added in Section 14.11 • Grignard reaction of nitriles—added in Section 15.7 • Reaction of diorganocuprates with acid halides—added in Section 16.4 • Alpha bromination of carboxylic acids—added in Section 17.3 • Amino acid metabolism—simplified coverage, Section 20.4 • Amino acid biosynthesis—simplified coverage, Section 20.5 • Final comments on metabolism—added in Section 23.10 • Nucleotide metabolism—simplified coverage, Section 24.9 39144_ FM_i-xxiv.indd xix 8/26/09 10:48:54 AM

PREFACE Nucleotide biosynthesis-simplified coverage.Section 24.10 An Introduction to Natural Products Chem- There is n ore thar of biol enough organic chemistry in this book,along with t far is that all the stude 0 medical school.will n any about eauty Features of the Second Edition Reaction Mechanisms evertical presentati ned in ction mechanisms that has my c Che h stry with Bic ecome ps prm s.Withhs n seea fo occurring at eac 14.10 591 fo 22.7 on page 912 for Visualization of Biological Reactions One of the most important goals of this book is to demystify biological chem- istry-to show students how the mechanisms of biological reactions are the same as those of laboratory organic reactions.Toward this end.and to let students more easily visualize the changes that occur during reactions of large biomolecules.I use an innovative method for focusing attention on the reacting parts in large molecules by "ghosting"the nonreacting parts.See Figure 13.6 on page 522,for example. Other Features "Why do we have to learn this?" I've so many times that duction chapter now es Why apter? paragraph that te st ent why th e mate out e cover ains how the organic chemistry in each chapter relates The Worked Examples in each chapter are titled to give students a frame of reference.Each Worked Example includes a Strategy and worked-out Solution,followed by Problems for students to try on their own. A Lagniappe-a Louisiana Creole word meaning"something extra"-is provided at the end of each cha s to stu- dents'lives.New Lagnia os in this editio Chemistry and on Liquids asgreen reaction solvents. Visualizing Chemistry problems at the end of each chapter offer stude cules rather than simply interpreting structural foasn y to see mistry in a Summaries and Key Word lists at the ends of chapters help students focus on the key concepts in that chapter

xx preface • Nucleotide biosynthesis—simplified coverage, Section 24.10 • “Secondary Metabolites: An Introduction to Natural Products Chem￾istry”—new Chapter 25 There is more than enough organic chemistry in this book, along with a coverage of biological chemistry that far surpasses what is found in any other text. My hope is that all the students we teach, including those who worry about medical school, will come to agree that there is also logic and beauty here. Features of the Second Edition Reaction Mechanisms The innovative vertical presentation of reaction mechanisms that has become a hallmark of all my texts in retained in Organic Chemistry with Biological Applications. Mechanisms in this format have the reaction steps printed ver￾tically, while the changes taking place in each step are explained next to the reaction arrows. With this format, students can see what is occurring at each step in a reaction without having to jump back and forth between structures and text. See Figure 14.10 on page 581 for a chemical example and Figure 22.7 on page 912 for a biochemical example. Visualization of Biological Reactions One of the most important goals of this book is to demystify biological chem￾istry—to show students how the mechanisms of biological reactions are the same as those of laboratory organic reactions. Toward this end, and to let students more easily visualize the changes that occur during reactions of large biomolecules, I use an innovative method for focusing attention on the reacting parts in large molecules by “ghosting” the nonreacting parts. See Figure 13.6 on page 522, for example. Other Features • “Why do we have to learn this?” I’ve been asked this question by students so many times that I thought I should answer it upfront. Thus, the intro￾duction to every chapter now includes “Why This Chapter?”—a brief paragraph that tells students why the material about to be covered is important and explains how the organic chemistry in each chapter relates to biological chemistry. • The Worked Examples in each chapter are titled to give students a frame of reference. Each Worked Example includes a Strategy and worked-out Solution, followed by Problems for students to try on their own. • A Lagniappe—a Louisiana Creole word meaning “something extra”—is provided at the end of each chapter to relate real-world concepts to stu￾dents’ lives. New Lagniappes in this edition include essays on Green Chemistry and Ionic Liquids as green reaction solvents. • Visualizing Chemistry problems at the end of each chapter offer students an opportunity to see chemistry in a different way by visualizing mole￾cules rather than simply interpreting structural formulas. • Summaries and Key Word lists at the ends of chapters help students focus on the key concepts in that chapter. 39144_ FM_i-xxiv.indd xx 8/26/09 10:48:54 AM

PREFACE Reaction Summaries at the ends of chapte ns from that chapter into one complete list.y rea An overview titled "A Preview of Carbonyl Chemistry,"following Chap ter 13.highlights the idea that studying organic chemistry works by both summarizing past ideas and looking ahead to new ones. The latest IUPAC nomenclature rules,as updated in 1993,are used in this text Thorough media integration with OWL for Organic Chemistry,an online homewor k assessment program,is provided to help students practice and test es param OWL rized end- apter questions text(marked in the text with).An access code is required.Visit www cengage.com/owl to register. Students can work through animated versions of the text's Active Figures at the Student Companion site,which is accessible from www.cengage .com/chemistry/mcmurry. Acknowledgments I thank all the people who helped to shape this book and its message.At Brooks/Cole Cengage Learning they include:Lisa Lockwood,executive edi tor:Sandra Kiselica,senior development editor;Amee Mosley.executive mar keting manager:Teresa Trego,senior production manager;Lisa Weber,senio media editor Elizabeth Woods,assistant editor,and Suzanne Kastner at Graphic Worl They incud eful to colleagues who reviewed the manuscript for this book REVIEWERS OF THE SECOND EDITION Peter Alaimo,Seattle University Rizalia Klausmeyer,Baylor University Paul Sampson,Kent State University Sheila Browne,Mount Holyoke Bette Kreuz,University of Michigan Martin Semmelhack,Princeton College University Gordon Gribble.Dartmouth College Manfred Reinecke,Texas Christian Megan Tichy,Texas A&M University John Grunwell,Miami University University Eric Kantorowski,California Frank Rossi,State University of New Polytechnic State University York.Cortland Kevin Kittredge,Siena College Miriam Rossi,Vassar College REVIEWERS OF FIRST EDITION Helen E.Blackwell.University of Th Wisconsin Joseph Chihade,Carleton College Paul Martino,Flathead Valley Andrew Morehead,East Carolina Robert S.Coleman,Ohio State Community College University University Eugene Mash.University of Arizon K.Barbara Schowen.University of John Hoberg.University of Wvoming Pshemak Maslak,Pennsylvania State Kansas Eric Kantorowski,California University Polvtechnic State University

preface xxi • Reaction Summaries at the ends of chapters bring together the key reac￾tions from that chapter into one complete list. • An overview titled “A Preview of Carbonyl Chemistry,” following Chap￾ter 13, highlights the idea that studying organic chemistry works by both summarizing past ideas and looking ahead to new ones. • The latest IUPAC nomenclature rules, as updated in 1993, are used in this text. • Thorough media integration with OWL for Organic Chemistry, an online homework assessment program, is provided to help students practice and test their knowledge of important concepts. For this second edi￾tion, OWL includes parameterized end-of-chapter questions from the text (marked in the text with ). An access code is required. Visit www .cengage.com/owl to register. • Students can work through animated versions of the text’s Active Figures at the Student Companion site, which is accessible from www.cengage .com/chemistry/mcmurry. Acknowledgments I thank all the people who helped to shape this book and its message. At Brooks/Cole Cengage Learning they include: Lisa Lockwood, executive edi￾tor; Sandra Kiselica, senior development editor; Amee Mosley, executive mar￾keting manager; Teresa Trego, senior production manager; Lisa Weber, senior media editor; Elizabeth Woods, assistant editor, and Suzanne Kastner at Graphic World. I am grateful to colleagues who reviewed the manuscript for this book. They include: REVIEWERS OF THE SECOND EDITION Peter Alaimo, Seattle University Sheila Browne, Mount Holyoke College Gordon Gribble, Dartmouth College John Grunwell, Miami University Eric Kantorowski, California Polytechnic State University Kevin Kittredge, Siena College Rizalia Klausmeyer, Baylor University Bette Kreuz, University of Michigan– Dearborn Manfred Reinecke, Texas Christian University Frank Rossi, State University of New York, Cortland Miriam Rossi, Vassar College Paul Sampson, Kent State University Martin Semmelhack, Princeton University Megan Tichy, Texas A&M University Bernhard Vogler, University of Alabama, Huntsville REVIEWERS OF FIRST EDITION Helen E. Blackwell, University of Wisconsin Joseph Chihade, Carleton College Robert S. Coleman, Ohio State University John Hoberg, University of Wyoming Eric Kantorowski, California Polytechnic State University Thomas Lectka, Johns Hopkins University Paul Martino, Flathead Valley Community College Eugene Mash, University of Arizona Pshemak Maslak, Pennsylvania State University Kevin Minbiole, James Madison University Andrew Morehead, East Carolina University K. Barbara Schowen, University of Kansas 39144_ FM_i-xxiv.indd xxi 8/26/09 10:48:54 AM

PREFACE Ancillaries to Accompany This Book For Students STUDY GUIDE AND SOLUTIONS MANUAL Written by Susan McMurry.this manual provides complete answers and explanations to all in-text and end-of- chapter exercises.The PowerLecture Instructor's CD contains a three-chapter preview.ISBN:0-495-39145-X WL OWL FOR ORGANIC CHEMISTRY (ONLINE WEB LEARNING) Instant Access【 OWL for Organic Chemistry (four semesters):ISBN-10: 3:978-0-495 5102 with e-B 0r4 cMurry's Second Edition(four semesters):ISBN-10:0-495-39150-6;1SBN-13:978-0-495-39150-0 and Peter Lillya ofthe Unive sity of Massachusetts Devel n Vin ork at One od a ach used th che interfac an up ve owL fo and ac nt to dfacilitate tion.You can soloct from tutors simulati and short answer qu ch emically.and contextu- and owL script and subscript as well eterization owI for or eanic Chemistry offers more than 6000 questions and includes an upgrade to the latest version of MarvinSketch,an advanced molecular drawing rogram for drawing grad- able structures.For this second edition,OWL includes parameterized end-of- chapter questions from the text(marked in the text with).New questions are authored by David W.Brown.Florida Gulf Coast University. When you become an OWL user,you can expect service that goes far beyond the ordinary.OWL is continually enhanced with online learning tools to address the various learning styles of today's students such as: e-Books,which offer a fully integrated electronic textbook linked to OWL questions Quick Prep review courses that help students learn essential skills to suc- ceed in General and Organic Chemistry ing bond distances and angles and for r more info orm ion,visit w oks/Cole Cengage Leamning representative ngage.com/owl STUDENT COMPANION WEBSITE Students can sions of the text's Act es at the Student accessible fr /mo pan PUSHING ELECTRONS:A GUIDE FOR STUDENTS OF ORGANIC CHEMISTRY.THIRD EDITION Written by Daniel P.Weeks,this workbook is designed to help stu- dents learn techniques of electron pushing.Its programmed approach empha- sizes repetition and active participation.ISBN:0-03-020693-6

xxii preface Ancillaries to Accompany This Book For Students STUDY GUIDE AND SOLUTIONS MANUAL Written by Susan McMurry, this manual provides complete answers and explanations to all in-text and end-of￾chapter exercises. The PowerLecture Instructor’s CD contains a three-chapter preview. ISBN: 0-495-39145-X OWL FOR ORGANIC CHEMISTRY (ONLINE WEB LEARNING) Instant Access to OWL for Organic Chemistry (four semesters): ISBN-10: 0-495-05102-0; ISBN-13: 978-0-495-05102-2 Instant Access to OWL with e-Book for McMurry’s Second Edition (four semesters): ISBN-10: 0-495-39150-6; ISBN-13: 978-0-495-39150-0 Authored by Steve Hixson and Peter Lillya of the University of Massachusetts, Amherst, and William Vining of the State University of New York at Oneonta. Developed at the University of Massachusetts, Amherst, used by thousands of chemistry students, and featuring an updated and more intuitive instructor interface, OWL for Organic Chemistry is a customizable online learning sys￾tem and assessment tool that reduces faculty workload and facilitates instruc￾tion. You can select from various types of assignments—tutors, simulations, and short answer questions that are numerically, chemically, and contextu￾ally parameterized—and OWL can accept superscript and subscript as well as structure drawings. With parameterization, OWL for Organic Chemistry offers more than 6000 questions and includes an upgrade to the latest version of MarvinSketch, an advanced molecular drawing program for drawing grad￾able structures. For this second edition, OWL includes parameterized end-of￾chapter questions from the text (marked in the text with ■). New questions are authored by David W. Brown, Florida Gulf Coast University. When you become an OWL user, you can expect service that goes far beyond the ordinary. OWL is continually enhanced with online learning tools to address the various learning styles of today’s students such as: • e-Books, which offer a fully integrated electronic textbook linked to OWL questions • Quick Prep review courses that help students learn essential skills to suc￾ceed in General and Organic Chemistry • Jmol molecular visualization program for rotating molecules and measur￾ing bond distances and angles To view an OWL demo and for more information, visit www.cengage.com/owl or contact your Brooks/Cole Cengage Learning representative. STUDENT COMPANION WEBSITE Students can work through animated ver￾sions of the text’s Active Figures at the Student Companion site, which is accessible from www.cengage.com/chemistry/mcmurry. PUSHING ELECTRONS: A GUIDE FOR STUDENTS OF ORGANIC CHEMISTRY, THIRD EDITION Written by Daniel P. Weeks, this workbook is designed to help stu￾dents learn techniques of electron pushing. Its programmed approach empha￾sizes repetition and active participation. ISBN: 0-03-020693-6 39144_ FM_i-xxiv.indd xxii 8/26/09 10:48:55 AM

PREFACE SPARTANMODEL ELECTRONIC MODELING KITAof easy-to-use builder for the ion of m th on CD-ROM. gna databa es,d a Tuto vare Us mole ost out of your course 1SBN:0-495-01793-0 For Instructors POWERLECTURE WITH EXAMVIEW AND JOININTM INSTRUCTOR'S CD/DVD PACKAGE ISBN-10:0-495-39146-8:ISBN-13:978-0-495-39146-3 PowerLecture PowerLecture is a dual-platform,one-stop digital library and presentation tool that includes: Prepared Microsoft PowerPoint Lecture Slides by Richard Morrison of the University of Georgia that cover all key points from the text in a con- venient format that you can enhance with your own materials or with additional interactive video and animations from the CD-ROM for person- alized,media-enhanced lectures. e libraries in powerPoint and in ipeg format that toyt art most nhoto phs.and all um ed tables in the text.These files can be used to print transparencies or to create your own PowerPoint lectures. Electronic files for the Test Bank. Sample chapters from the student Solutions Manual and Study Guide. ting softy 250 items i n print or online JoinIn clicker questions authored for this text,for use with the classroom response system of your choice.Assess student progress with instant Joinln quizzes and polls,and display student answers seamlessly within the Microsoft PowerPoint slides of your own lecture.Consult your Brooks Cole Cengage Learning representative for more details. FACULTY COMPANION WEBSITE Accessible from www.cer mcmurry,this website provides downloadable files for the WebCT and Black- board versions of ExamView Computerized Testing. TEST BANK Revised by Bette Kreuz of the University of Michigan-Dearborn. this Test Bank includes more than 1000 multiple-choice and matching ques- tions,with detailed answers,in preprinted test forms corresponding to the main text organization.The Test Bank is available on the instructor's Power- Lecture CD as electronic files and in ExamView format.Instructors can cus tomize tests using the Test Bank files on the PowerLecture CD-ROM.ISBN: 0-495-39149-2 ORGANIC CHEMISTRY LABORATORY MANUALS Brooks/Cole,Cengage Learr is pleased to offer you a choice of organic chemistry laboratory m ered to fit you stry.Cus vww.signature- mizabl

preface xxiii SPARTANMODEL ELECTRONIC MODELING KIT A set of easy-to-use builders allow for the construction and 3-D manipulation of molecules of any size or complexity—from a hydrogen atom to DNA and everything in between. This kit includes the SpartanModel software on CD-ROM, an extensive molecular database, 3-D glasses, and a Tutorial and Users Guide that includes a wealth of activities to help you get the most out of your course. ISBN: 0-495-01793-0 For Instructors POWERLECTURE WITH EXAMVIEW® AND JOININ™ INSTRUCTOR’S CD/DVD PACKAGE ISBN-10: 0-495-39146-8; ISBN-13: 978-0-495-39146-3 PowerLecture is a dual-platform, one-stop digital library and presentation tool that includes: • Prepared Microsoft® PowerPoint® Lecture Slides by Richard Morrison of the University of Georgia that cover all key points from the text in a con￾venient format that you can enhance with your own materials or with additional interactive video and animations from the CD-ROM for person￾alized, media-enhanced lectures. • Image Libraries in PowerPoint and in JPEG format that provide electronic files for all text art, most photographs, and all numbered tables in the text. These files can be used to print transparencies or to create your own PowerPoint lectures. • Electronic files for the Test Bank. • Sample chapters from the Student Solutions Manual and Study Guide. • ExamView testing software, with all test items from the printed Test Bank in electronic format, which enables you to create customized tests of up to 250 items in print or online. • JoinIn clicker questions authored for this text, for use with the classroom response system of your choice. Assess student progress with instant quizzes and polls, and display student answers seamlessly within the Microsoft PowerPoint slides of your own lecture. Consult your Brooks/ Cole Cengage Learning representative for more details. FACULTY COMPANION WEBSITE Accessible from www.cengage.com/chemistry/ mcmurry, this website provides downloadable files for the WebCT and Black￾board versions of ExamView Computerized Testing. TEST BANK Revised by Bette Kreuz of the University of Michigan–Dearborn, this Test Bank includes more than 1000 multiple-choice and matching ques￾tions, with detailed answers, in preprinted test forms corresponding to the main text organization. The Test Bank is available on the instructor’s Power￾Lecture CD as electronic files and in ExamView format. Instructors can cus￾tomize tests using the Test Bank files on the PowerLecture CD-ROM. ISBN: 0-495-39149-2 ORGANIC CHEMISTRY LABORATORY MANUALS Brooks/Cole, Cengage Learn￾ing is pleased to offer you a choice of organic chemistry laboratory manuals catered to fit your needs. Visit www.cengage.com/chemistry. Customizable laboratory manuals also can be assembled. Go to www.signature-labs.com/ specializations/chemistry.html for more information. 39144_ FM_i-xxiv.indd xxiii 8/26/09 10:48:55 AM