Higher Education

Organic Chemistry, 6th Edition

  • William H. Brown Beloit College
  • Christopher S. Foote University of California, Los Angeles
  • Brent L. Iverson University of Texas, Austin
  • Eric Anslyn University of Texas at Austin
  • ISBN-10: 084005498X  |  ISBN-13: 9780840054982
  • 1296 Pages
  • Previous Editions: 2002, 2002, 1995
  • © 2012 | Published
  • College Bookstore Wholesale Price = $308.25
  • Newer Edition Available
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About

Overview

Providing a modern introduction to organic chemistry for students majoring in chemistry, health, and the biological sciences, ORGANIC CHEMISTRY, Sixth Edition, is both student-friendly and cutting-edge and incorporates the latest advances in the field. Professors Brown, Iverson, and Anslyn have all won teaching awards at their respective schools, and they use their skills to build upon the text's hallmarks of unified mechanistic themes, focused problem-solving, use of applied problems from the pharmaceutical field, and unrivaled visuals. Thoroughly updated throughout, the book offers numerous biological examples for premed students, a wide range of in-text learning tools, and integration with the OWL for Organic Chemistry homework and tutorial system, which now includes an interactive multimedia eBook. In this edition, to help students understand reaction mechanisms, the authors offset reaction mechanisms in a stepwise fashion and now emphasize similarities between related mechanisms using just four different characteristics: breaking a bond, making a new bond, adding a proton and taking a proton away. Numerous resources help ensure student success in the course, including a running margin glossary, a mini in-text study guide, and more in-chapter examples than any other text on the market. Emphasizing "how-to" skills, this edition is packed with challenging synthesis problems, medicinal chemistry problems, and unique roadmap problems.

Features and Benefits

  • VISUAL IMPACT. This text is distinguished by its striking, full-color art program (250 pieces of numbered art and over 1,000 pieces of in-text art). The book paints a detailed picture of the orbital nature of electron density in Chapter 1 by focusing on the interplay between the two complementary approaches to orbital descriptions: valence bond theory and molecular orbital theory. High-quality photos show organic chemistry as it occurs in the laboratory and in everyday life; electrostatic potential maps illustrate structure and reactivity; the spectra in the book reflects the latest imagery; and the book includes state-of-the-art, mathematically accurate molecular models.
  • HOW-TO BOXES. To facilitate student success in the course, insightful "How-To" boxes highlight the survival skills necessary to learn and master organic chemistry. Integrated throughout the text at key points, these essential skills include "How To: Draw Curved Arrows and Push Electrons," "How To: Draw Chiral Molecules," "How To: Solve NMR Spectral Problems," and many more.
  • BIOLOGY CONNECTION. Although still a predominantly synthetic organic chemistry text, the book explicitly links concepts to biological chemistry topics--drawing in biology majors, premed students, and others who will soon go on to biochemistry. "Connections to Biological Chemistry" boxes discuss the applications of organic chemistry to biology to a wide range of topics.
  • REACTIONS IN CONTEXT. These problems apply organic chemistry to medicinal chemistry and the pharmaceutical sciences.
  • MORE IN-CHAPTER WORKED EXAMPLES THAN ANY OTHER TEXT: Featuring a pedagogy normally reserved for general chemistry texts, the book offers more worked examples than other texts, followed by corresponding problems without answers and a multitude of end-of-chapter problems, including challenging, research-based essay problems, multi-step synthesis problems, reactions in context problems and roadmap problems.
  • CHEMICAL CONNECTIONS BOXES. These boxes illustrate applications of organic chemistry to everyday settings, with topics ranging from Radical Autoxidation to Drugs that Lower Plasma Levels of Cholesterol.
  • BUILT-IN STUDY TOOLS. Outlined end-of-chapter summaries highlight all-important new terms found in the chapter to provide students with a mini in-text study guide. The outlines are linked to the end-of-chapter problems and to the corresponding sections of the text. Summaries of Key Reactions annotate each reaction and key it to the section where it is discussed, making it easy for students to see similarities and differences among reactions.
  • OWL INTEGRATION. Improve student learning outcomes with OWL, the #1 online homework and learning system for chemistry. Developed by chemistry instructors for teaching chemistry, OWL includes course management tools that make homework management a breeze, as well as advanced reporting and grade book features that save time in grading homework and tracking student progress. OWL enables you to address students' different learning styles through tutorials, simulations, visualization exercises, and algorithmically-generated homework questions with answer-specific feedback. With OWL's mastery learning approach, students work at their own pace until they understand each concept/skill. OWL includes an eBook, enhanced with multimedia learning tools.

Table of Contents

1. Covalent Bonding and Shapes of Molecules.
2. Alkanes and Cycloalkanes.
3. Stereochemistry and Chirality.
4. Acids and Bases.
5. Alkenes.
6. Reactions of Alkenes.
7. Alkynes.
8. Haloalkanes, Halogenation, and Radical Reactions.
9. Nucleophilic Substitution and B-Elimination.
10. Alcohols.
11. Ethers, Sulfides, and Epoxides.
12. Infrared Spectroscopy.
13. Nuclear Magnetic Resonance Spectroscopy.
14. Mass Spectrometry.
15. Introduction to Organometallic Compounds.
16. Aldehydes and Ketones.
17. Carboxylic Acids.
18. Functional Derivatives of Carboxylic Acids.
19. Enolate Anions and Enamines.
20. Dienes, Conjugated Systems, and Pericyclic Reactions.
21. Benzene and the Concept of Aromaticity.
22. Reactions of Benzene and Its Derivatives.
23. Amines.
24. Catalytic Carbon–Carbon Bond Formation.
25. Carbohydrates.
26: Lipids.
27. Amino Acids and Proteins.
28. Nucleic Acids.
29. Organic Polymer Chemistry.
Appendices:
1. Thermodynamics and the Equilibrium Constant.
2. Major Classes of Organic Acids.
3. Bond Dissociation Enthalpies.
4. Characteristic 1H-NMR Chemical Shifts.
5. Characteristic 13C Chemical Shifts.
6. Characteristic IR Absorption Frequencies.
7. Electrostatic Potential Maps.
8. Summary of Stereochemical Terms.
9. Summary of the Rules of Nomenclature.
10. Common Mistakes in Arrow Pushing.
11. Organic Chemistry Roadmaps.
GLOSSARY G-1.
INDEX I-1.

What's New

  • REVISED PRESENTATION OF MECHANISMS. Mechanisms are presented in a clear, stepwise fashion with written commentary accompanying each mechanistic step so verbal learners can learn alongside more visually oriented learners. In this edition, many mechanisms have been broken up into more steps to increase student understanding. In addition, the authors emphasize similarities between related mechanisms using just four different characteristics: breaking a bond, making a new bond, adding a proton, and taking a proton away. Chapter 9, Analysis of Several Competitions Between Substitution and Eliminations, includes new information to help students better define these mechanisms.
  • REVISED ROADMAP PROBLEMS. These unique problems relate to the authors' organic chemistry roadmap, which compares organic chemistry to a roadmap with functional groups analogous to cities and reactions analogous to the roads between them. Creating a cumulative, graphical representation of the different reactions students encounter in the context of important functional groups, the organic chemistry roadmap helps students visualize how to interconvert different functional groups, which often requires different reactions from different chapters, by simply identifying the most direct path on the roadmap.
  • SLIGHT REORGANIZATION. The authors have combined related topics to enhance student understanding by merging parts of Chapter 24 with Chapter 20. Chapter 20 has been renamed "Dienes, Conjugated Systems and Pericyclic Reactions."
  • ENHANCEMENTS IN OWL. In addition to updating the online mastery and end-of-chapter questions correlated to the book, the accompanying OWL FOR ORGANIC CHEMISTRY online learning system includes a new interactive eBook, enhanced with rich multimedia learning tools.

Learning Resource Bundles

Choose the textbook packaged with the resources that best meet your course and student needs. Contact your Learning Consultant for more information.

Printed Text + OWL with Cengage YouBook (6 months) Instant Access Code

ISBN-10: 1133426670  | ISBN-13: 9781133426677

List Price = $422.95  | CengageBrain Price = $422.95  | College Bookstore Wholesale Price = $318.25

This Bundle Includes:

  • Organic Chemistry
    List Price = $410.95  | CengageBrain Price = $410.95  | College Bookstore Wholesale Price = $308.25
  • OWL (6 months) Instant Access
    List Price = $99.00  | College Bookstore Wholesale Price = $99.00


Bundle: Text + Pushing Electrons: A Guide for Students of Organic Chemistry, 3rd + OWL eBook (24 months) Printed Access Card

ISBN-10:  1133536751  | ISBN-13:  9781133536758

List Price = $436.95  | CengageBrain Price = $436.95  | College Bookstore Wholesale Price = $328.25

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  • Pushing Electrons: A Guide for Students of Organic Chemistry, 3rd
    List Price = $165.95  | CengageBrain Price = $165.95  | College Bookstore Wholesale Price = $124.50
  • Organic Chemistry
    List Price = $410.95  | CengageBrain Price = $410.95  | College Bookstore Wholesale Price = $308.25
  • OWL (24 months) Printed Access Card
    List Price = $129.00  | College Bookstore Wholesale Price = $96.75


Bundle: Text + OWL eBook (24 months) Printed Access Card

ISBN-10:  1111488118  | ISBN-13:  9781111488116

List Price = $429.95  | College Bookstore Wholesale Price = $323.25

This Bundle Includes:

  • Organic Chemistry
    List Price = $410.95  | CengageBrain Price = $410.95  | College Bookstore Wholesale Price = $308.25
  • OWL (24 months) Printed Access Card
    List Price = $129.00  | College Bookstore Wholesale Price = $96.75


Printed Text + OWL with Cengage YouBook (24 months) Instant Access Code

ISBN-10:  1133426689  | ISBN-13:  9781133426684

List Price = $429.95  | CengageBrain Price = $429.95  | College Bookstore Wholesale Price = $323.25

This Bundle Includes:

  • Organic Chemistry
    List Price = $410.95  | CengageBrain Price = $410.95  | College Bookstore Wholesale Price = $308.25
  • OWL (24 months) Instant Access
    List Price = $129.00  | College Bookstore Wholesale Price = $129.00


Bundle: Text + OWL eBook with Student Solutions Manual (24 months) Printed Access Card

ISBN-10:  111148810X  | ISBN-13:  9781111488109

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This Bundle Includes:

  • Organic Chemistry
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  • OWL with Student Solutions Manual (24 months) Printed Access Card
    List Price = $211.00  | College Bookstore Wholesale Price = $158.25


Bundle: Text + Study Guide with Student Solutions Manual

ISBN-10:  1133074146 | ISBN-13:  9781133074144

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This Bundle Includes:

  • Organic Chemistry
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  • Study Guide with Student Solutions Manual
    List Price = $236.95  | CengageBrain Price = $236.95  | College Bookstore Wholesale Price = $177.75


Supplements

All supplements have been updated in coordination with the main title. Select the main title's "About" tab, then select "What's New" for updates specific to title's edition.

For more information about these supplements, or to obtain them, contact your Learning Consultant.

Instructor Supplements

PowerLecture with ExamView® and JoinIn™ Student Response System  (ISBN-10: 1111426899 | ISBN-13: 9781111426897)

This dual-platform CD/DVD-ROM package is an all-in-one digital library and presentation tool with Test Bank, ExamView electronic software, JoinIn classroom response system software and clicker questions, and more. Text-specific PowerPoint® lecture slides cover all key points from the text, and you can enhance them with your own materials or with additional interactive video and animations. Image Libraries (PowerPoint and JPEG formats) including electronic files for text art, photographs, and numbered tables allow you to print transparencies or create your own PowerPoint lectures. The CD also includes electronic files for the Test Bank and three sample chapters from the Student Solutions Manual and Study Guide, and the Chemistry Multimedia Library DVD-ROM, which contains animations, simulations, and movies for all chemistry subjects, organized by topic for lecture presentations.

Study Guide with Student Solutions Manual  (ISBN-10: 1111426813 | ISBN-13: 9781111426811)

The best way for students to learn organic chemistry concepts is to work relevant and interesting problems on a daily basis. Authored by Brent and Sheila Iverson, The University of Texas at Austin, this comprehensive manual offers detailed solutions to all in-text and end-of-chapter problems in the Sixth Edition of the core text. It helps students achieve a deeper intuitive understanding of the material through constant reinforcement and practice--ultimately resulting in much better preparation for in-class quizzes and tests, as well as national standardized tests such as the DAT and MCAT.

List Price = $236.95  | CengageBrain Price = $236.95  | College Bookstore Wholesale Price = $177.75

Maruzen International Organic Modeling Kit #1013  (ISBN-10: 0840053258 | ISBN-13: 9780840053251)

Help your students understand not only molecular structures, but also atom hybrid orbitals, bond angle, and bond length with the MARUZEN INTERNATIONAL ORGANIC MODELING KIT #1013, designed in consultation with Cengage Learning. This modeling kit can be packaged with any Cengage Learning organic chemistry text at a discounted price.

List Price = $34.95  | College Bookstore Wholesale Price = $25.75

Organic Chemistry: A Guided Inquiry  (ISBN-10: 0618974121 | ISBN-13: 9780618974122)

Designed for use as a supplement to a traditional text to encourage active and collaborative learning in the classroom, this student activity book incorporates new methods for teaching chemistry that reflect current research on how students learn. The purpose of the guided inquiry approach is to teach students to think analytically and collaboratively in teams, like scientists do, rather than teaching them to memorize important conclusions arrived at by great scientists of the past. By looking carefully at new problems, constructing logical conclusions based on observations, and discussing the merits of their conclusions with peers, students develop a stronger conceptual understanding of and appreciation for the material. Honing their logical and empirical skills enables students to better pursue not only chemistry, but any other complex sets of ideas.

List Price = $130.95  | CengageBrain Price = $130.95  | College Bookstore Wholesale Price = $98.25

Student Supplements

Study Guide with Student Solutions Manual  (ISBN-10: 1111426813 | ISBN-13: 9781111426811)

Offering detailed solutions to all in-text and end-of-chapter problems, this comprehensive guide helps you achieve a deeper intuitive understanding of chapter material through constant reinforcement and practice. The result is much better preparation for in-class quizzes and tests, as well as national standardized tests such as the DAT and MCAT.

List Price = $236.95  | CengageBrain Price = $236.95  | College Bookstore Wholesale Price = $177.75

Organic Chemistry: A Guided Inquiry  (ISBN-10: 0618974121 | ISBN-13: 9780618974122)

Designed for use as a supplement to a traditional text to encourage active and collaborative learning in the classroom, this activity book incorporates new methods for teaching chemistry that reflect current research on how students learn. The purpose of the guided inquiry approach is to teach you to think analytically and collaboratively in teams, like scientists do, rather than teaching you to memorize important conclusions arrived at by great scientists of the past. By looking carefully at new problems, constructing logical conclusions based on observations, and discussing the merits of your conclusions with peers, you'll develop a stronger conceptual understanding of and appreciation for the material. Honing your logical and empirical skills enables you to better pursue not only chemistry, but any other complex sets of ideas.

List Price = $130.95  | CengageBrain Price = $130.95  | College Bookstore Wholesale Price = $98.25

Meet the Author

Author Bio

William H. Brown

William H. Brown is emeritus professor of chemistry at Beloit College, where he was twice named Teacher of the Year. His teaching responsibilities include organic chemistry, advanced organic chemistry, and, more recently, special topics in pharmacology and drug synthesis. He received his Ph.D. from Columbia University under the direction of Gilbert Stork and did postdoctoral work at California Institute of Technology and the University of Arizona. He is a coauthor on ORGANIC CHEMISTRY, 10e (Cengage Learning).

Christopher S. Foote

Christopher S. Foote received his B.S. in 1957 from Yale University and his Ph.D. in 1962 from Harvard University. His scholarly credits include Sloan Fellow 1965-1967; Guggenheim Fellow 1967-1968; ACS Baekland Award, 1975; ACS Cope Scholar, 1994; Southern California Section ACS Tolman Medal, 1996; President, American Society for Photobiology, 1988-1989; and Senior Editor, ACCOUNTS OF CHEMICAL RESEARCH. He was Professor of Chemistry at UCLA.

Brent L. Iverson

Brent L. Iverson received his Ph.D. from Stanford University in 1982 and currently teaches at University of Texas, Austin. He is a distinguished teacher and respected researcher. Iverson's research group has developed methods for recombinant antibody or enzyme cloning and has directed its evolution. In collaboration with the Georgiou group, he pioneered a novel E. coli surface expression/FACS selection technology that has allowed the group to enhance antibody affinity.

Eric Anslyn

Eric Anslyn is the Norman Hackerman Professor of Chemistry at The University of Texas at Austin. Highly respected in organic chemistry, he earned his Ph.D. from the California Institute of Technology and has won numerous teaching awards. Anslyn's research focuses on the cutting-edge area of bioorganic chemistry.