Preface xxvii protecting roups.and oxidations using chromiumfree reagents such as the Swern and Dess-Martin oxidations. Reaction for ciples used to predict mechanisms.Problem-solving sections develop basic techniqe approaching mechanism problems,and they work to minimiz aing whether th or free radical in oushing arrows"to illustrate these individual steps.Important mechanisms are high lighted by placing them in the Mechanism and Key Mechanism boxes. Introduction to Mechanisms Usin Free-Radical Halogenation: been debated for man years.The principal obection to free-rdicahalo ation is that i isnota useful synthetie reaction.But useful reactions such as nucleophilic substitution and Gas-phase free-radic logenation allows a clearer treatmer ntages as a synthetic reacton are dis nts ar Organic Synthesis:Organic synthesis is stressed throughout this book,with progressive naterials to find the target compou Typical yields have been provided for many synthetic reactions,although I hope stu- misuse these numbers.Too often students consider the yi characteristic j as t nelting point of a compound is fix In practice.n a factor of T student with excellent technique might obtain. copy is one of the most important tools of the dabopy and t disc the tfrftlhdetonerretmo meap地eo eoR etive with IR and NMR spe to helr copy.and with ilable in the ple problems and Study Problems located throughout the text show how the clues from various p an int hich Nomenclature:The most recent IUPAC nomenclature is stresse ed throughout the book velop students'familiarity.Teach m the l chemistry.biology.and medicine uses common names such as methyl ethyl ketone,isovaleri acid,methyl tert-butyl ether,y-aminobutyric acid,and s-caprolactam.This book nomenclature is often preferred,yet it encourages familiarity common names as well
Preface xxvii synthetic techniques are also included, such as Suzuki coupling and the Heck reaction, asymmetric hydrogenation and epoxidation, reductions using DIBAL-H, olefin metathesis, silyl ether protecting groups, and oxidations using chromium-free reagents such as the Swern and Dess–Martin oxidations. 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 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 free-radical 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 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 and Study Problems located throughout the text show how the clues from various spectra are combined to propose a structure. The emphasis is on helping students develop an intuitive feel for using spectroscopy to solve structural problems. A comprehensive list of the spectroscopy problems found in each chapter is available online a www.pearsonhighered.com. Nomenclature: The most recent 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, -aminobutyric acid, and -caprolactam. This book emphasizes why systematic nomenclature is often preferred, yet it encourages familiarity with common names as well. g e
xxviii Preface Key Mechanism Boxes 20 Key Mechanism Boxes are the fundamental mechanistic A nisms.Each Key Mechanism Box reinforces studen 7 understanding with steps and explanations that describe the the reaction mechanism (how the reaction occurs),a specific exam Mechanism Boxes Racemiration in the St Reaction 小 locusing on the in steps or eac casily as the thumb through the chapter. Multi-Part Problems. SOLVED FRORIEN 5-5 Over 1400(mostly multi-part)problems provide immediate review 60gof(+)-butm-2-o and reinforcement as students learn the material and make sure the understand each section well enough before moving on to the next PROBLEM 5-16 rically pure ()-btn-The io f
xxviii Preface Mechanism Boxes 150 Mechanism Boxes help students understand how reactions occur by focusing on the individual steps of each reaction. The Mechanism Boxes are shaded in blue so students can locate them easily as they thumb through the chapter. Key Mechanism Boxes 20 Key Mechanism Boxes are the fundamental mechanistic principles that recur throughout the course. They are the mechanisms that compose most of the longer, more complex mechanisms. Each Key Mechanism Box reinforces student understanding with steps and explanations that describe the the reaction mechanism (how the reaction occurs), a specific example of the mechanism for reinforcement, and a concluding problem or question so students can assess their understanding. Multi-Part Problems Over 1400 (mostly multi-part) problems provide immediate review and reinforcement as students learn the material and make sure they understand each section well enough before moving on to the next
Preface xxix Problem Solving Strategies Problem-Solving Strategies help PRORLEM-SOIWING SIRATEGY dents pieces and help students establish thoughtful methods for approach- ing complicated problems synthesis. pgma st,Classity the Problem Solving Hints Problem Solving Hints appear in the margins and remind students of facts or princi- Problem-solving Hint r gives Every object has a mirror image.Is chiral.Same:The obiect is achiral Application Boxes chemistry.Drugs,Environment,Medicine,Fuels,and Green Chemistry. Application Drugs Ethanol,made chiral by the presence of Bicyclic moleculeare found nmany a deuterium(o)isonef the early examples natural product structures.Cocaine isa Application:Fuels derivative of bicyclo..n Tetraethy lead (TEL),formula OH (CHaCHaPb,was once added to gasc one-c was banned from automotive oasoline (S)-1-deuterioethanol OCH becauset inactivates catalytic convert H H in coca leaves for theodengines
Preface xxix Problem Solving Hints Problem Solving Hints appear in the margins and remind students of facts or principles that may be useful for solving common types of problems. They are the tips the author gives his own students to help them work problems and reviews for exams. Problem Solving Strategies Problem-Solving Strategies help students break down the multitude of complex problems into simpler pieces and help students establish thoughtful methods for approaching complicated problems–like those that require proposing mechanisms and developing multi-step synthesis. Application Boxes Application Boxes throughout demonstrate the relevance of Organic Chemistry to students’ lives and areas of interest including contemporary topics such as Biochemistry, Drugs, Environment, Medicine, Fuels, and Green Chemistry
XXX Preface Chapter Goals and Essential Problem Solving Skills students navigate the material and assess their under standing and proficiency throughout each chapter in MasteringChemistry)while students can study more effectively by solving problems directly tied to ESSENTIAL PROBLEM-SOLVING SKILLS IN CHAPTER4 chapter goals. 8 ems 4-5 and 57 Summary SUMMARY Types of isomers nly in the orien ion of the atoms in spoce s that are not mirror imaees of e ch othe E-trans iso
xxx Preface Chapter Goals and Essential Problem Solving Skills Enhanced pedagogical tools including Chapter Goals and Essential Problem Solving Skills help students navigate the material and assess their understanding and proficiency throughout each chapter. Professors can use these features at-a-glance to assign homework related to specific skills (also available in MasteringChemistry) while students can study more effectively by solving problems directly tied to chapter goals. Summary Summary Feature: The Summaries, located in key locations throughout the chapters highlight important information using charts and graphs when possible
Resources in Print and Online Description ry from designed and refined with a olatform deli es and e to each IRDVD Instructor Supplement rated collection of rese s to hel gnande tpresn2 I two presem files of the ce Manual.as we as the Test bank Testbank nstructor Supplement o huild at wD-dIm onal drawing Chemistry re xxxi
xxxi Supplement Available in Print? Available Online? Instructor or Student Supplement Description MasteringChemistry® ✓ Instructor and Student Supplement MasteringChemistry from Pearson has been designed and refined with a single purpose in mind: to help educators create that moment of understanding with their students. The Mastering platform delivers engaging, dynamic learning opportunities—focused on your course objectives and responsive to each student’s progress—that are proven to help students absorb course material and understand difficult concepts. By complementing your teaching with our engaging technology and content, you can be confident your students will arrive at that moment—the moment of true understanding. (Available at www.masteringchemistry.com) Solutions Manual by Jan William Simek ✓ Instructor and Student Supplement This Solutions Manual provides detailed solutions to all in-chapter as well as the end-of-chapter exercises in the text. IRDVD ✓ ✓ Instructor Supplement This resource provides an integrated collection of resources to help instructors make efficient and effective use of their time. This DVD features all artwork from the text, including figures and tables in PDF format for highresolution printing, as well as four pre-built PowerPoint™ presentations. The first presentation contains the images embedded within PowerPoint slides. The second includes a complete lecture outline that is modifiable by the user. The final two presentations contain worked “in chapter” sample exercises and questions to be used with classroom iClicker systems. This DVD also contains movies, animations, and electronic files of the Instructor’s Resource Manual, as well as the Test bank. Testbank ✓ ✓ Instructor Supplement This testbank contains over 3000 multiple-choice, true/false and matching questions. It is available in print format, in the TestGen program, in word format and in included in the item library of MasteringChemistry.. Organic Molecular Kit (Darling) ✓ Instructor and Student Supplement Darling Models™ contain various pieces used to build atoms, bonds, and molecules. This model kit allows you to build molecules and see the threedimensional aspects of organic chemistry that can only be imagined in a two-dimensional drawing. Prentice Hall Molecular Model Kit for Organic Chemistry ✓ Instructor and Student Supplement The Prentice Hall molecular model set allows you to build space-filling and ball-and-stick models of organic molecules. The components are precisiontooled from quality plastics, are virtually indestructible, and come in a sturdy plastic case for easy storage. Provides a useful Instruction Book—with photos, diagrams, and concise discussions of chemical principles. Resources in Print and Online