Organic Chemistry: A Brief Survey of Concepts and Applications (6th Edition)

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9780139241192: Organic Chemistry: A Brief Survey of Concepts and Applications (6th Edition)

This application-based book presents essential, core concepts of basic organic chemistry in an engaging, easy-to-read format. It is ideal for the individual seeking a hands-on approach to understanding structure, nomenclature, physical properties, uses and applications, and chemical reactions of organic compounds. Unique engaging techniques get the reader involved in the learning process, such as a "Getting Involved" feature at the end of each section and several dozen mini-essays which connect theory to real life issues. Ideal for medical health professionals and anyone involved in consumer health issues.

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From the Publisher:

Drawing on the authors' 25 years of teaching experience, this text has been specifically designed for the unique needs and interests of students taking a short course in organic chemistry. It introduces carefully selected core concepts of organic chemistry, brings them together with unifying principles, and relates them to applications of interest to students and society in general.

From the Inside Flap:

Preface

It is a privilege to present the sixth edition of our introductory organic chemistry textbook coincidentally with the beginning of the twenty-first century. We have been honored by opportunities for revision, translations into other languages, and the use of this textbook in many parts of the world as well as the United States. Our appreciation goes to the thousands of students and faculty members who have used this book during its 22-year history. Thank you; this experience has been a special part of our professional and personal lives.

The following is a description of the focus and approach of Organic Chemistry, as well as how students and their instructors might best use the textbook.

This treatment of organic chemistry is designed for a short course that consists of one quarter, one semester, or two quarters. It is written especially for students who are not chemistry majors but are in fields for which chemistry is a core course. Accordingly, we have limited the scope of the presentation and have introduced applications related to agriculture, life sciences, health and medicine, and consumer, environmental, and societal issues. The selection and organization of material is consistent with this short course focus. For each topic and concept we have tried to write clear and thorough explanations that promote understanding and critical thinking. We have tried to focus on the learning process, and to write in a way to engage the student intellectually. The facts learned in a college course are important, but the promotion of active learning and the appreciation for the material will outlast memorization.

Most introductory organic chemistry courses are organized around a functional group approach in which molecules with specific structural units (functional groups) are classified in families that share similar physical and chemical properties and rules of nomenclature. Using the functional group approach we have organized the chapters as follows: Organization

Chapters 1 to 3: The basis for structure and nomenclature. Structure and nomenclature of organic compounds are inextricably related. Competency in these areas is essential if students are to understand and appreciate the physical and chemical properties of organic compounds or to develop a practical understanding of applications. These topics are a major portion of every chapter of the book as each functional group is presented.

In Chapter 1, structure and bonding are organized around just a few ideas, and each is clearly presented with the interrelationships shown. Chapter 2 covers the structure and nomenclature of alkanes including cycloalkanes and conformational isomers. Chapter 3 presents the structure and nomenclature of alkenes and includes a discussion of geometric isomerism. A wealth of exercises accompany each chapter to allow the student a hands-on experience with structure and nomenclature.

Chapter 4: An Introduction to Organic Reactions. The basic simplicity of organic chemistry is illustrated here: three types of reactions - substitution, addition, and elimination; three types of mechanisms - carbocation, carbanion, and free radical; and a rather short list of structural features that are considered reaction sites. A free radical substitution reaction of alkanes and a carbocation elimination reaction for the preparation of alkenes conclude the chapter.

Chapters 5 and 6: Reactions of Alkenes, Alkynes, and Aromatic Compounds. Based on structural concepts covered in Chapters 1 to 3 and the principles of organic reactions from Chapter 4, addition and substitution reactions, both with carbocation mechanisms, are presented in these chapters.

Chapters 7 and 8: Stereochemistry and Organic Halides. Chirality, enantiomerism, diastereomerism, and R,S configurations are presented in Chapter 7; a concluding short section relates these concepts to reactions already presented. Chapter 8 then uses the principles of organic reactions and stereochemistry in the

study of nucleophilic substitution and elimination reactions.

Chapters 9 and 10: Alcohols and Ethers; Amines. There are two reasons we place these chapters here. The concepts of acidity and basicity provide a conceptual thread that is clearly evident in both chapters, and the characteristic reactions of nucleophilic substitution and elimination continue nicely from Chapter 8.

Chapters 11 to 13: Aldehydes and Ketones; Carboxylic Acids and Their Derivatives. After three chapters involving nucleophilic substitution reactions, we can now concentrate on nucleophilic addition using aldehydes and ketones (Chapter 11). Chapter 12 focuses on the nomenclature and acidity of carboxylic acids. Then in Chapter 13, nucleophilic acyl substitution reactions of carboxylic acids and their derivatives are presented. The concepts of acidity and basicity often difficult for students-as well as the nucleophilic reactions begun in Chapters 8, 9, and 10 are reiterated and reinforced.

Chapters 14 to 17: Biochemistry - Carbohydrates, Fats and Oils, Proteins, and Nucleic Acids. The functional groups and reactions introduced in Chapters 9 to 13 lead logically to chapters on biomolecules. In keeping with the interests of the students in this course, we cover each of these topics in some detail.

Chapter 18: Spectroscopy. Infrared ultraviolet-visible, proton and C-13 nuclear magnetic resonance, and mass spectrometry are presented concisely but in a way that allows significant experiences in problem solving. We realize that many instructors do not cover this chapter while others cover it at different places in the course. We have organized the material so this chapter can be introduced any time after Chapter 6 based on the student's knowledge of structure (Chapter 13 is another logical place for introduction because all the functional groups have been presented).

Connections boxes: There are more than 40 essays throughout the book written to connect organic chemistry to the real world. They include topics related to issues of energy, the environment, consumer goods, living organisms, health, disease, and medicine. Pedagogy

The following are learning tools available in this textbook:

Getting Involved: These special entries follow all major sections of each chapter and many of the subsections. Within these we try to engage the student in her/his own learning process. Each Getting Involved module will have one or more sections in the following order: Short questions: These questions are a first opportunity for a student to self-evaluate his or her comprehension of what was just read. Worked examples: Often there will be a worked example in this section. Other times there will be sufficient examples in the preceding reading. Practice problems: These provide an opportunity to work immediately with the material just presented. Reference to end-of-chapter problems: The internal textbook problems are immediate opportunities to "get involved." Appropriate, related problems from the end of the chapter are referenced here. Clear and complete explanations: We have emphasized a depth of understanding rather than breadth in this text. An emphasis on systematic, logical, and critical thinking minimizes memorization and maximizes real learning. Problems: Organic chemistry is a hands-on subject. A student has to work problems to really become adept with the material. This book has approximately 800 numbered problems distributed between in-chapter and end-of-chapter exercises. Included with these problems are some molecular model-building exercises that can be done with a variety of different model kits or with electronic model programs like Chem3D (Cambridge Soft). If you are interested, Prentice Hall can make model kits of Chem3D available with this text at a dramatic discount. Marginal definitions: A brief definition of each important term is printed in the margin next to its introduction. Reaction summaries: Summaries of all reactions are presented at the end of each chapter. Summary of IUPAC nomenclature: See the Appendix for this comprehensive, integrated summary. Glossary of terms: This appendix is an alphabetical listing of the terms defined in the margins in each chapter.

Other special features of this textbook include the following:

Soft cover, a second color: This textbook is significantly lighter and less expensive than hard-cover versions, and therefore is not as heavy a burden physically or economically. We are offering an alternative, especially when the cost of textbooks is such an issue on college campuses. We believe we have the explanations, illustrations, use of a second color, and exercises to provide a substantial intellectual experience and effectively promote learning. Subdivisions: We realize that instructors have their own creative organizational methods for teaching organic chemistry and that no textbook can exactly match the preferences of many, if any, instructors. We have included subheadings within each chapter to make assignment of topics and exercises, development of a course syllabus, and adaptation of this book to many teaching styles as easy as possible. Solutions Manual and Study Guide (ISBN 0-13-015480-6): An ancillary Solutions Manual and Study Guide is available that contains chapter summaries (outlined just as are the chapters) and solutions to each problem in the textbook. To ensure a consistent voice and style, we wrote this manual ourselves. Website at www prenhall/bailey: We have a companion Website developed by us and specifically designed for this textbook. We suspect it will always be a work in progress, but initially it will have the following features: Links to interesting Websites providing additional information and insight for each of the Connections essays. A tutorial on the use of Chem3D. Demonstration exercises on structure, isomerism, and stereochemistry.

We wish to thank our students and other users of the previous five editions of this text. We have appreciated the comments and suggestions of students and instructors and invite the same for this edition.

Drs. Philip and Christina Bailey
Department of Chemistry and Biochemistry
California Polytechnic State University
San Luis Obispo, California 93407

e-mail:
pbailey@ealpoly
cbailey@calpoly Acknowledgments

We wish to acknowledge the many people involved in bringing the sixth edition of this textbook to a successful conclusion. We owe a special debt of gratitude to our excellent editor, John Challice. We also wish to thank our production editor, Celeste Clingan of Accu-color, and our picture consultant, Mary Ann Price. The work of Karl Bailey and Nhu Y Tran Stressman in checking the solutions in the Solutions Manual is greatly appreciated. With much appreciation, we acknowledge the reviewers of the manuscript; they were exceedingly helpful.

Stuart R. Berryhill, California State University, Long Beach
Clair J. Cheer, San Jose State University
Loretta T. Dorn, Fort Hays State University
Jeffrey E. Elbert, South Dakota State University
Christopher M. Hadad, Ohio State University
Phillip D. Hampton, University of New Mexico
Cliff Harris, Albion College
Thomas R. Hays, Texas A & M University, Kingsville
James R. Hermanson, Wittenberg University
John C. Hogan, Louisiana State University
Tamera S. Janke, Southwest Missouri State University
Kenneth Johnson, Emporia State University
Francis M. Klein, Creighton University
James G. Macmillan, University of Northern Iowa
Rita S. Majerle, South Dakota State University William A. Meena, Rock Valley College
Todd A. Richmond, The Claremont Colleges
Ralph Shaw, Southeastern Louisiana University
Jason M. Stenzel, Southern Connecticut State University
Richard T. Taylor, Miami University
Anthony P Toste, Southwest Missouri State University
Maria Vogt, Bloomfield College
Mark S. Workentin, University of Western Ontario

We also wish to thank our students and colleagues at Cal Poly. Finally, we express our gratitude for the important work and contributions of Prentice Hall regional representatives.

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