Organic Chemistry, Fourth Edition

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9780131407480: Organic Chemistry, Fourth Edition

This innovative book from acclaimed educator Paula Bruice is organized in a way that discourages rote memorization. The author's writing has been praised for anticipating readers' questions, and appeals to their need to learn visually and by solving problems. Emphasizing that learners should reason their way to solutions rather than memorize facts, Bruice encourages them to think about what they have learned previously and apply that knowledge in a new setting. KEY TOPICS The book balances coverage of traditional topics with bioorganic chemistry, highlights mechanistic similarities, and ties synthesis and reactivity together—teaching the reactivity of a functional group and the synthesis of compounds obtained as a result of that reactivity. For the study of organic chemistry.

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About the Author:

Paula Yurkanis Bruice was raised primarily in Massachusetts, Germany, and Switzerland and was graduated from the Girls' Latin School in Boston. She received an A.B. from Mount Holyoke College and a Ph.D. in chemistry from the University of Virginia. She received an NIH postdoctoral fellowship for study in biochemistry at the University of Virginia Medical School, and she held a postdoctoral appointment in the Department of Pharmacology at Yale Medical School.

She is a member of the faculty at the University of California, Santa Barbara, where she has received the Associated Students Teacher of the Year Award, the Academic Senate Distinguished Teaching Award, and two Mortar Board Professor of the Year Awards. Her research interests concern the mechanism and catalysis of organic reactions, particularly those of biological significance. Paula has a daughter and a son who are physicians and a son who is a lawyer. Her main hobbies are reading mystery/suspense novels and her pets (three dogs, two cats, and a parrot).

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To the Instructor

My guiding principle in writing this book was to create a text that focuses on the student, one that presents the material in a way that encourages students to think about what they have already learned and then apply this knowledge in a new setting. Some students look upon organic chemistry as a course they have to endure simply because it is part of their course of study. Others may get the impression that learning organic chemistry is akin to learning a foreign "language"—a diverse collection of molecules and reactions—the language of a country that they will never visit. I hope, however, that as students proceed through their study of organic chemistry, they see that it is a subject that unfolds and grows and allows them to use what they learn at the beginning of the course to predict what follows. Countering the impression that the study of organic chemistry necessarily involves simply memorizing molecules and reactions, this book revolves around shared features and unifying concepts, and it emphasizes principles that can be applied again and again. I want students to learn how to apply what they have learned to a new setting, reasoning their way to a solution, rather than memorizing a multitude of facts. I also want to encourage students to see that organic chemistry is integral to biology as well as to their daily lives.

From the comments I have received from colleagues and students using previous editions, the book is working in the way I had hoped. As much as I enjoy having faculty tell me that their students are scoring higher than ever before on tests, nothing is more rewarding than hearing from the students themselves. Many students have generously attributed their success in organic chemistry to this book&3#51;not giving themselves nearly enough credit for how hard they studied to achieve that success. And they always seem surprised that they have come to love "orgo" (on the East Coast) or "o-chem" (on the West Coast). I also hear from many premedical students who say that the book gave them the permanent understanding of organic chemistry that allowed them to find the organic chemistry section of the MCAT to be the easiest part.

In striving to make this fourth edition even more useful to students, I have relied on constructive comments from many of you. For these, I am extremely grateful. I also have kept a journal of questions that students asked when they came to my office. These questions let me know what sections in the book needed clarifying and what answers in the Study Guide and Solutions Manual needed more in-depth explanations. Most important, this analysis showed me where new problems could reduce the chance that students using the new edition would ask these same questions. Because I teach large classes, I have a vested interest in foreseeing potential confusion before it arises. In this edition, many sections have been rewritten to optimize readability and comprehension. A variety of new in-chapter and end-of-chapter problems will help students master organic chemistry through problem solving. There are also new interest boxes to show students the relevance of organic chemistry and there are additional margin notes to remind students of important concepts and principles.

I hope you find the fourth edition even more appealing to your students. As always, I am eager to hear your comments—positive comments are the most fun, but critical comments are the most useful.

A Functional Group Approach with a Mechanistic Organization That Ties Together Synthesis and Reactivity

The organization of this book is designed to discourage rote memorization. The presentation of functional groups is organized around mechanistic similarities—electrophilic additions, radical substitutions, nucleophilic substitutions, eliminations, electrophilic aromatic substitutions, nucleophilic acyl substitutions, and nucle,ophilic additions. This organization allows a lot of material to be understood based on unifying principles of reactivity.

Instead of discussing the synthesis of a functional group when its reactivity is discussed—reactions that generally have little to do with one an other—I discuss the synthesis of the compounds that are formed as a result of the functional group's reactivity. In Chapter 4, for example, students learn about the reactions of alkenes, but they do not learn at this point about the synthesis of alkenes. Instead, they learn about the synthesis of alkyl halides, alcohols, ethers, and alkanes—the compounds formed when alkenes react. Because alkenes are synthesized from the reactions of alkyl halides and alcohols, the synthesis of alkenes is covered when the reactions of alkyl halides and alcohols are discussed. Tying together the reactivity of a functional group and the synthesis of compounds resulting from the functional group's reactivity prevents the student from having to memorize lists of unrelated reactions. It also results in a certain economy of presentation, allowing more material to be covered in less time.

Although memorizing different ways a particular functional group can be prepared is hard on students and can be somewhat counterproductive to their mastering organic chemistry, it is useful to have a compilation of reactions that yield a particular functional group when designing multistep syntheses. For this purpose, the different reactions that yield a particular functional group are compiled in Appendix IV. As students learn how to design syntheses, they appreciate the importance of reactions that change the carbon skeleton of a molecule; these reactions are compiled in Appendix V.

A Modular Format

Different people teach differently, so I have tried to make the book as modular as possible. The spectroscopy chapters (Chapters 13 and 14) have been composed so that they may be covered at any time. For those who prefer to teach spectroscopy at the beginning of the cours—or in a separate laboratory course—I placed a table of the functional groups at the beginning of Chapter 13. For those who prefer to cover carbonyl chemistry earlier in the course, Part 6 (Carbonyl Compounds and Amines) can be covered before Part 5 (Aromatic Compounds). I anticipate that most instructors will cover the first 23 chapters during a year-long course and will then choose among the remaining chapters, depending on personal preference and the interests of the students enrolled in the course. Those teaching students whose interests are primarily in the biological sciences might be more inclined to cover Chapter 24 (Catalysis), Chapter 25 (The Organic Mechanisms of the Coenzymes • Metabolism), Chapter 26 (Lipids), and Chapter 27 (Nucleosides, Nucleotides, and Nucleic Acids). Those teaching courses designed for chemistry or engineering majors may decide to include Chapter 28 (Synthetic Polymers) and Chapter 29 (Pericyclic Reactions). The book ends with a chapter on drug discovery and design—a topic that in my experience interests students sufficiently that they will choose to read it on their own, even if it is not covered in the course.

A Bioorganic Emphasis

Today, many students taking organic chemistry are interested in the biological sciences. Therefore, bioorganic material is introduced throughout this text to allow students to see that organic chemistry and biochemistry are not separate entities, but two parts of a continuum of knowledge. Once students learn how such things as electron delocalization, leaving-group tendency, electrophilicity, and nucleophilicity affect the reactions of simple organic compounds, they can appreciate how these same factors are involved in the reactions of more complicated organic molecules such as enzymes, nucleic acids, and vitamins. I have found that the economy of presentation afforded by the first 21 chapters of this text (explained previously) makes it possible to devote more time to bioorganic topics.

In the first two-thirds of the book, the bioorganic material is limited primarily to the later sections of the chapters; as a result the material is available to the curious student, but the instructor is not compelled to introduce bioorganic topics into the course. For example, after the stereochemistry of organic reactions is presented, the stereoselectivity of enzymatic reactions is discussed; after alkyl halides are discussed, biological compounds used to methylate substrates are examined; after the methods chemists use to activate carboxylic acids are presented, the methods that cells use to activate these acids are explained; after condensation reactions are discussed, examples of biological condensation reactions are shown.

The six chapters of Part 7 (Chapters 22-27) specifically address bioorganic chemistry. They contain more chemistry than one would expect to find in a biochemistry text. Chapter 24 on catalysis, for example, explains the various modes of catalysis that occur in organic reactions and then shows that these are identical to the modes of catalysis that occur in enzymatic reactions. All of this is presented in a way that allows students to understand the lightning-fast rates of enzymatic reactions. Chapter 25 on coenzymes emphasizes the role of vitamin B1 as an electron delocalizer, vitamin K as a strong base, vitamin B12 as a radical initiator, biotin as a compound that can transfer a carboxyl group; and how the many different reactions of vitamin B6 are controlled by the overlap of p orbitals. Chapter 26 on lipids, covers the mechanisms of prostaglandin formation (allowing students to understand how aspirin works), fat breakdown, and terpene biosynthesis. Chapter 27 on nucleic acids explains mechanistically such topics as the chemical function of ATP (Its role is not to provide a magic shot of energy that allows an endothermic reaction to take place. Rather, its role is to provide a reaction pathway involving a good leaving group for a reaction that cannot occur because of a poor leaving group.) Students learn t...

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