Extend Learning Beyond the Classroom NEW for this edition!MasteringChemistry leads students through the process of solving problems while and enable profeto omreoporn ati e spent,mos t prob Student Tutorial neChemistnytuorialguidesndents Masteri isuse-paced tutorials that roi individualized coaching.These assignable,in- depth tutorials are designed to coach students ck specific to their indi- misconception Molecular Drawing Tool MasteringChemistry's new molecular drawing tool accommodates the diversity of structures and reaction mechanisms inherent to feanic chemistry while providing students with error-specific Mawve tuto on araw structures,skeletal structures,and complex mechanisms/arrow MasteringChemistry allows students to draw reaction mechanisms in a step-wise manner.Ranging in difficulty levels.the new mechanism problem types provide stu- dents with detailed.imm diate fee anter each step 8 m as to wheom they made their first mistake.Professors maintain con 14.车4、02 trol over the grade value of each mechanistic step and cP is em I book and can be acces with students to identify their misconceptions. 8 xxxii
xxxii Extend Learning Beyond the Classroom NEW for this edition! MasteringChemistry® leads students through the process of solving problems while promoting their understanding of chemical concepts. This assessment and tutorial program supplies quantifiable metrics and enables professors to compare their class performance against the national average on specific questions or topics. At a glance, professors can see class distribution of grades, time spent, most difficult problems, most difficult steps, and even the most common answer. Student Tutorial MasteringChemistry® tutorials guide students through the toughest topics in organic chemistry with self-paced tutorials that provide individualized coaching. These assignable, indepth tutorials are designed to coach students with hints and feedback specific to their individual misconceptions. MasteringChemistry allows students to draw reaction mechanisms in a step-wise manner. Ranging in difficulty levels, the new mechanism problem types provide students with detailed, immediate feedback after each step of their mechanism or, if assigned, feedback after completion of an entire multipart mechanism as to where they made their first mistake. Professors maintain control over the grade value of each mechanistic step and can limit student attempts as well as assign a more challenging mechanistic problem for credit alone. Every individual student attempt is recorded within the gradebook and can be accessed by professors as they work with students to identify their misconceptions. Molecular Drawing Tool MasteringChemistry’s new molecular drawing tool accommodates the diversity of structures and reaction mechanisms inherent to organic chemistry while providing students with error-specific feedback. A comprehensive tutorial on drawing with MarvinSketch within Mastering helps students get up and running quickly on their homework. The drawing tool supports Lewis structures, skeletal structures, and complex mechanisms/arrow pushing and evaluates multiple aspects of the student-created structures in order to provide the most precise feedback possible
Extend Leaming Beyond the Classroom xxxiii MasteringChemistry End of Chapter Problems ass w人 CH2 encourage students to apply their knowledge to new problems and provide an excellent source for quiz Gradebook Every assignment is automatically graded.At a glance, shades of red highlight vulnerable students and chal- enging assignments Gradebook Diagnostics class and ment over the duration of the course. Oreanic Chemistry
End of Chapter Problems Almost all Study Problems from the Eighth Edition of Wade are available within MasteringChemistry and can be automatically graded and assigned for homework or practice. A robust, additional problem set associated with each chapter in Wade can also be assigned to encourage students to apply their knowledge to new problems and provide an excellent source for quiz questions. MasteringChemistry® Gradebook Every assignment is automatically graded. At a glance, shades of red highlight vulnerable students and challenging assignments. Gradebook Diagnostics Gradebook Diagnostics provide unique insight into class and student performance. With a single click, charts summarize the most difficult problems, vulnerable students, grade distribution, and score improvement over the duration of the course. Extend Learning Beyond the Classroom xxxiii
Chapter-by-Chapter Changes Rpp IUPAC re .The section on acidity has been revised to include prese Chapter 2 Chapter 15 emohasire thhd .A new section.Colored Organic Compounds,has been eof hyd -LUMO concept of tes lea to a Chapter 3 dyes.pH indicators.and food colo. section iv-visible Analysis in biology and ormulas and Newman projectons. n added to introduce UV analysis in Chapter5 biochemistry,and to show the structural features of .The different types of chemical notation used to indicate biological molecules that are responsible for U\ An example of a in a clinica alkaline Chapter8 principles are used directly in medical technology. .Dihydroxylation has been updated to emphasize catalytic Chapter 16 methods. e2010i Chapter 9 (Nobel Prize 1996)and nanotubes Chapter 17 Chapter 11 thods of alcohol oxidat anding the discussion ofo adiontq preferable to the older chromium methods,including a ofh Hekcto (Nobel Prize 2010)are introduced,including methods of adcydes and eto TEMPOs preparing boronic ac synthesis are included. Chapter 12 Chapter 18 .An Application on the MALDI technique for mass spectral analysis of biological molecules has been added. .The chemistry of 1,3-dithianes has been deleted. .The use of DIBAL-H to reduce nitriles to aldehydes has Chapter 14 been added,as has the low-temperature reduction of .A new section covers the formation and cleavage of silyl alde s.Severa ethers,and their strategy and use as protecting groups on at inclu alcohols.This new material introduces the concept of xxxiv
xxxiv Every chapter begins with Chapter Goals and ends with Essential Problem-Solving Skills, including references to particular end-of-chapter problems that reinforce each skill. New problems, Problem-Solving Hints, Essential Terms, and Applications have been added to almost every chapter. All IUPAC names have been updated to current IUPAC recommendations. Chapter-by-Chapter Changes Chapter 1 ● The section on acidity has been revised to include inductive effects of substituents on the acidity of carboxylic acids, in addition to resonance effects and electronegativity. Chapter 2 ● The section on solubility has been expanded to emphasize the role of hydrogen bonding and molecular size in the role of water solubility of organic molecules. Chapter 3 ● New problems show the student how to interconvert and name structural formulas and Newman projections. Chapter 5 ● The different types of chemical notation used to indicate the three-dimensional spatial arrangement of bonds around carbon have been presented. Chapter 8 ● Dihydroxylation has been updated to emphasize catalytic methods. Chapter 9 ● New problems emphasizing synthesis and identification of unknown structures have been added. Chapter 11 ● Newer methods of alcohol oxidation (Swern, Dess–Martin) are introduced as environmentally preferable to the older chromium methods, including a description of a general, unifying mechanism of alcohol oxidation to aldehydes and ketones. TEMPO is shown as an oxidation catalyst to enhance hypochlorite oxidation. Chapter 12 ● An Application on the MALDI technique for mass spectral analysis of biological molecules has been added. Chapter 14 ● A new section covers the formation and cleavage of silyl ethers, and their strategy and use as protecting groups on alcohols. This new material introduces the concept of protecting groups earlier than acetals in Chapter 18. Problems using silyl ether chemistry reinforce the concept. ● Sharpless Asymmetric Epoxidation (Nobel Prize 2001) is presented in a problem. Chapter 15 ● A new section, Colored Organic Compounds, has been added to explain how the HOMO-LUMO concept of highly conjugated molecules leads to absorption in the visible region, and how that applies to natural products, dyes, pH indicators, and food colors. ● A new section, UV-Visible Analysis in Biology and Medicine, has been added to introduce UV analysis in biochemistry, and to show the structural features of biological molecules that are responsible for UV absorption. An example of a reagent used in a clinical analyzer that undergoes a color change when changed by alkaline phosphatase demonstrates how organic chemical principles are used directly in medical technology. Chapter 16 ● A new description of graphene (Nobel Prize 2010 in Physics) has been added in the section on Fullerenes (Nobel Prize 1996) and nanotubes. Chapter 17 ● A new section, Aromatic Substitutions Using Organometallic Reagents, has been added. In addition to expanding the discussion of organocuprate reagents, new discussions of the Heck reaction and Suzuki coupling (Nobel Prize 2010) are introduced, including methods of preparing boronic acids and esters for the Suzuki reaction. Several problems illustrating these reactions in synthesis are included. Chapter 18 ● The chemistry of 1,3-dithianes has been deleted. ● The use of DIBAL-H to reduce nitriles to aldehydes has been added, as has the low-temperature reduction of esters with DIBAL-H to produce aldehydes. Several problems have been added that include these reactions in synthesis
Chapter-by-Chapter Changes XXXV Chapter19 Chapter 23 The use of amine salts as phase-transfer catalysts has been .The use of silyl ethers of carbohydrates to alter the deleted. solubility properties is incorporated in problems. Hofmann rearrangement of amides has been deleted. .The Fischer proof of glucose has been condensed to an extended problem. Chapter 21 Newly added reactions are DIBAl-H reduction of ester and Chapter 26 dialkylcuprate reaction with acid chlorides to produce ketones. Ring-opening metathesis polymerization (ROMP)has been demonstrated in a problem. Acknowledgments Iam pleased to thank the many talented people who helped with this revision.More than anyone else.Jan William 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 inputonallof the cna and b elped to write and or the new sections.He also c tions throughout the w ess.and who helped to shape this new edition. ningandr Eighth Edition Accuracy Reviewers haAn Califomia Polytechnic State University Eighth Edition Prescriptive Reviewers Jon Antilla University of South Florida Alline Somlai Delta State University Solomon Weldegirma University of South Florida Reviewers of Previous Editions David Alor Merritt B.Andrus Brigham You g Un versity Dan Becker Bob Bly ity of South Ca Loyola Univ Stohn's University
Chapter-by-Chapter Changes xxxv Chapter 19 ● The use of amine salts as phase-transfer catalysts has been deleted. ● Hofmann rearrangement of amides has been deleted. Chapter 21 ● Newly added reactions are DIBAL-H reduction of esters, and dialkylcuprate reaction with acid chlorides to produce ketones. Chapter 23 ● The use of silyl ethers of carbohydrates to alter the solubility properties is incorporated in problems. ● The Fischer proof of glucose has been condensed to an extended problem. Chapter 26 ● Ring-opening metathesis polymerization (ROMP) has been demonstrated in a problem. Acknowledgments I am pleased to thank the many talented people who helped with this revision. More than anyone else, Jan William 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 to write and edit all of the new sections. He also coauthored most of the new problems and all of the Answers to Selected Problems. Particular thanks are also due to Developmental Editor John Murdzek, who 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. Eighth Edition Accuracy Reviewers David A. Boyajian Palomar College Hasan Palandoken California Polytechnic State University Susan Schelbe Metro State College of Denver Alline Somlai Delta State University Eighth Edition Prescriptive Reviewers Jon Antilla University of South Florida Eric Brown Loyola University Lake Shore Timothy B Clark Western Washington University James Fletcher Creighton University Hasan Palandoken California Polytechnic State University Keith Osbourne Pascoe Georgia State University Anthony J Pearson Case Western Reserve Owen Priest Northwestern University K.C. Russell Northern Kentucky University Alline Somlai Delta State University Solomon Weldegirma University of South Florida Reviewers of Previous Editions Jung-Mo Ahn University of Texas at Dallas David Alonso Andrews University Merritt B. Andrus Brigham Young University Arthur J. Ashe University of Michigan Bill Baker University of South Florida Dan Becker Loyola University John Berger Montclair State University Bob Bly University of South Carolina Mary Boyd Loyola University, Chicago Hindy Bronstein Fordham College at Lincoln Center David Brown St. John’s University
xxxvi Chapter-by-Chapter Changes Philip Brown North Carolina State University gzhi tem University Barbara Colonna Richard Conley Maria de GracaVicente Chris Goman William Jenks lowa State Univ bisp University of Flor Virginia ommonw alth University o th e m ed,or professional and competent people. about howthe boo quickly in the next changes and improvemer tion ope ma ced That's the most important reason why I wrote it. L.G.Wade.Jr. Walla Walla,Washington
xxxvi Chapter-by-Chapter Changes Philip Brown North Carolina State University Christine Brzezowski University of Alberta Patrick Buick Florida Atlantic University David Cantillo Hillsborough Community College Dee Ann Casteel Bucknell University Amber Charlebois William Paterson University Cai Chengzhi University of Houston Barry Coddens Northwestern University Jamie Lee Cohen Pace University Barbara Colonna University of Miami Richard Conley Middlesex County College Robert Crow St. Louis College of Pharmacy Maria de GracaVicente Louisiana State University Chris Gorman North Carolina State University Geneive Henry Susquehanna University William Jenks Iowa State University Przemyslaw Maslak Pennsylvania State University Kristen Meisenheimer Cal Polytechnic at San Luis Obispo Stephen A. Miller University of Florida Guillermo Moyna University of the Sciences in Philadelphia Rabi Musah University at Albany Anthony J. Pearson CaseWestern Reserve University Allan Pinhas University of Cincinnati Stanley Raucher University ofWashington Suzanne Ruder Virginia Commonwealth University David Son Southern Methodist University Joseph B. Wachter Michigan State University Finally, I want to thank the people at Pearson, whose dedication and flexibility contributed to the completion of this project. Executive Editor, Jeanne Zalesky and Senior Project Editor, Jennifer Hart kept the project moving, ensured the needed resources were available, and made many useful comments and suggestions. Project Managers Marisa Taylor, Kate Thomas, and Shari Toron who kept the production process organized, on track, and on schedule. It has been a pleasure working with all these thoroughly professional and competent people. I’ve enjoyed working on this new edition, and I hope that it is an improved fine-tuning of the seventh 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 next 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. L. G. Wade, Jr. Walla Walla, Washington