Organic Chemistry (5th Edition)

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9780130338327: Organic Chemistry (5th Edition)

In a highly accessible fashion, this top-selling book bridges the gap between conceptual understanding and actual application—while strongly emphasizing the development of problem-solving skills. The book focuses on traditional organic chemistry topics and offers up-to-date aspects of spectroscopy, relevant photographs, and many applications to polymer chemistry integrated throughout the book.

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About the Author:

L. G. "Skip" Wade decided to become a chemistry major during his sophomore ear at Rice University, while taking organic chemistry from Professor Ronald M. Magi After receiving his B.A. from Rice in 1969, Wade went on to Harvard University, ere he did research with Professor James D. White. While at Harvard, he served as the Head Teaching Fellow for the organic laboratories and was strongly influenced by the teaching methods of two master educators, Professors Leonard K. Nash and Frank H. Westheimer.

After completing his Ph.D. at Harvard in 1974, Dr. Wade joined the chemistry faculty at Colorado State University. Over the course of fifteen years at Colorado State, Dr. Wade taught organic chemistry to thousands of students working toward careers in all areas of biology, chemistry, human medicine, veterinary medicine, and environmental studies. He also authored research papers in organic synthesis and in chemical education, as well as eleven books reviewing current research in organic synthesis. Since 1989, Dr. Wade has been a chemistry professor at Whitman College, where he teaches organic chemistry and pursues research interests in organic synthesis and forensic chemistry. Dr. Wade received the A. E. Lange Award for Distinguished Science Teaching at Whitman in 1993.

Dr. Wades interest in forensic science has led him to testify as an expert witness in court cases involving drugs and firearms, and he has worked as a police firearms instructor, drug consultant, and boating safety officer. He also enjoys repairing and restoring old violins and bows, which he has done professionally for many years.

Excerpt. © Reprinted by permission. All rights reserved.:

To the Student

As you begin your study of organic chemistry, yon might feel overwhelmed by the number of compounds, names, reactions, and mechanisms that confront you. You may even wonder whether you can learn all this material in a single year. The most important function of a textbook is to organize the material to show that most of organic chemistry consists of a few basic principles and many extensions and applications of these principles. Relatively little memorization is required if you grasp the major concepts and develop flexibility in applying those concepts. Frankly, I have a poor memory, and I hate memorizing lists of information. I don't remember the specifics of most of the reactions and mechanisms in this book, but I can work them out by remembering a few basic principles, like "alcohol dehydrations usually go by E1 mechanisms:"

Still, you'll have to learn some facts and fundamental principles to serve as the working "vocabulary" of each chapter. As a student, I learned this the hard way when I made a D on my second organic chemistry exam. I thought organic would be like general chemistry, where I could memorize a couple of equations and fake my way through the exams. For example, in the ideal gas chapter, I would memorize pv = nrT, and I was good to go. When I tried the same approach in organic, I got a D. We learn by making mistakes, and I learned a lot in organic chemistry.

In writing this book, I've tried to point out a small number of important facts and principles that should be learned to prepare for solving problems. For example, of the hundreds of reaction mechanisms shown in this book, about 20 are the fundamental mechanistic steps that combine into the longer, more complicated mechanisms. I've highlighted these fundamental mechanisms in Key Mechanism boxes to alert you to their importance. Spectroscopy is another area where a student might feel pressured to memorize hundreds of facts, such as NMR chemical shifts and infrared vibration frequencies. I couldn't do that, so I've always gotten by with knowing about a dozen NMR chemical shifts and about a dozen IR vibration frequencies, and knowing how they are affected by other influences. I've listed those important infrared frequencies in Table 12-2 and the important NMR chemical shifts in Table I 3-3.

Don't try to memorize your way through this course. It doesn't work; you have to know what's going on so you can apply the material. Also, don't think (like I did) that you can get by without memorizing anything. Read the chapter, listen carefully to the lectures, and work the problems. The problems will tell you whether or not you know the material. If you can do the problems, you should do well on the exams. If you can't do the problems, you probably won't be able to do the exams, either. If you keep having to look up something to do the problems, that item is a good one to learn.

Here are some hints I give my students at the beginning of the course:

  1. Read the material in the book before the lecture (expect 13-15 pages per lecture). Knowing what to expect and what is in the book, you can take fewer notes and spend more time listening and understanding the lecture.
  2. After the lecture, review you notes and the book, and do the in-chapter problems. Also, read the material for the next lecture.
  3. If you are confused about something, visit your instructor during office hours immediately, before you fall behind. Bring your attempted solutions to problems with you to show your instructor where you are having trouble.
  4. To study for the exam, begin by reviewing each chapter and your notes, then concentrate on the end-of-chapter problems. Also use old exams for practice, if available.

Remember the two "golden rules" of organic chemistry.

  1. DON'T GET BEHIND! The course moves too fast, and it's hard to catch up.
  2. WORK LOTS OF PROBLEMS. Everyone needs the practice, and problems show where you need more work.

Study Aids

Several kinds of study aids are provided to emphasize and review the most important points.

Summary Tables. Whenever a large amount of material lends itself to a concise summary, a summary table is provided to compare and contrast this material. For example, the following summary table compares the factors affecting SN1 and SN2 reactions:

Reaction Summaries. At the conclusion of each section on syntheses or reactions of a functional group ("Reactions of Alkenes," for example), a summary table is provided for efficient review. Each summary, highlighted by a blue background, includes cross-references to reactions that are discussed elsewhere.

Mechanism Boxes. In this edition, I've added anew design element to help you fin(( the important mechanisms easily when you review a chapter. These mechanism boxes (about 100 total) have large blue headings that make them easy to see as you thump through the chapter. Please let me know if you think of ways they might be made more helpful. In choosing which mechanisms to put in boxes, I've tried to include most of the standard mechanisms that most students can work through and understand after they've finished studying the chapter.

The most important of these mechanisms (about 20) are in Key Mechanism boxes. These are the fundamental mechanistic principles that make organic chemistry (and biochemistry) work. They are the pieces that compose most of the other, longer mechanisms given in the book. Thirty years from now, even if you don't remember anything else from your organic chemistry course, I hope you will still understand these fundamental ways that compounds react.

Problems. The in-chapter problems appear right after the relevant sections of the text. These problems provide immediate review and reinforcement of the material as you learn it, helping to make sure you understand each section well enough before moving on to the next. Later, end-of-chapter problems promote additional review and practice. Your instructor may choose to assign specific problems that reflect the emphasis of the lectures. Problems with red stars (*) are more difficult problems that require extra thought and perhaps some extension of the material presented in the chapter.

Solved Problems where appropriate, solved problems (highlighted by a beige background) are provided to show how you might approach a particular type of problem and what kind of answer is expected. For example, a solved problem might work through a mechanism to show how it is broken down into individual steps and how red curved arrows show movement of electrons.

Solved problems are often followed by another problem to give students an immediate opportunity to practice the principles covered in the solved problems.

Glossaries. Each chapter ends with a glossary that defines and explains technical terms introduced in that chapter. New terms defined in the glossary are printed in boldface the first time they appear in the chapter. Don't think of the glossaries as simply dictionaries for looking up words. The Index works better for that. The real purpose of the glossaries is as study aids for reviewing the material. Read through them after you read each chapter, and they will help to jog your memory as you go over the definitions and make sure you understand and can use all the new terms.

Chapter 8 Glossary

addition. A reaction involving an increase in the number of groups attached to the alkene and a decrease in the number of elements of unsaturation. (p. 314)

anti addition: An addition in which two groups add to opposite faces of the double bond (as in addition of Br2). (p. 326)

electrophilic addition: An addition in which the electrophile bonds to one of the double-bonded carbons first, followed by the nucleophile. (p. 315)

syn addition: An addition in which two groups add to the same face of the double bond (as in osmium tetroxide hydroxylation). (p. 326)

addition polymer (chain-growth polymer). A polymer that results from rapid addition of one molecule at a time to a growing polymer chain, usually with a reactive intermediate (canon, radical, or anion) at the growing end of the chain. (p. 352)

alkoxymercuration. The addition of mercuric acetate to an alkene in an alcohol solution, forming an alkoxymercurial intermediate. Demercuration gives an ether. (p. 326)

Problem-Solving Strategies. The problem-solving strategies (highlighted by a green background) suggest methods for approaching complicated problems, such as those that require proposing mechanisms and developing multi-step syntheses. Students often have trouble seeing how to approach problem solving, and these strategies are meant to help you break problems down into simpler pieces. Although organic chemistry cannot be reduced to a rote process that guarantees an answer, experienced chemists instinctively approach problems in ways that are more likely to lead to solutions. The suggestions in the problem-solving discussions approximate what an experienced chemist is likely to do in approaching these problems. They serve as a starting point, not a guaranteed route to the answers.

Problem-Solving Hints. These suggestions (green headings in the marginal column at the side of the page) are provided to remind you of facts or principles that are likely to be useful for solving common types of problems. These are the tips I give my own students when I help them work problems and review for exams. These hints highlight material that is sometimes overlooked but plays an important role in solving problems.

Essential Problem-Solving Skills. This list is provided at the end of each chapter to remind you of the kinds of skills needed to solve typical problems associated with the material in that chapter. When you finish a chapter, this list c...

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