Higher Education

Organic Chemistry, Hybrid Edition, 7th Edition

  • includes OWLv2 24-Months Printed Access Card
  • William H. Brown Beloit College
  • Brent L. Iverson University of Texas, Austin
  • Eric Anslyn University of Texas, Austin
  • Christopher S. Foote University of California, Los Angeles
  • ISBN-10: 1285426509  |  ISBN-13: 9781285426501
  • 1072 Pages
  • Previous Editions: 2012
  • © 2014 | Published
  • College Bookstore Wholesale Price = $163.50

About

Overview

Providing a modern introduction to organic chemistry for students majoring in chemistry, health, and the biological sciences, this revised and updated edition of ORGANIC CHEMISTRY 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 pre-med students, a wide range of in-text learning tools, and integration with both a homework and tutorial system and an interactive multimedia eBook. To help students understand reaction mechanisms, the authors offset them in a stepwise fashion and 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. Organic chemistry reaction roadmaps take a center stage in this edition with new pull-out maps designed in a stepwise manner by chapter. These roadmaps will help students to devise their own reaction pathways. Numerous resources help ensure student success in the course, including a running margin glossary, a mini end-of-chapter 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.This briefer, paperbound version does not contain the end-of-chapter problems, which can be assigned in OWLv2, the online homework and learning system for this book. Access to OWLv2 and the MindTap Reader eBook is included with the Hybrid version. The MindTap Reader is the full version of the text, with all end-of-chapter questions and problem sets.

Features and Benefits

  • 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. Many mechanisms have been broken 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. A new primer (right before Chapter 6) on Developing a Reaction Mechanism sets this material apart for easy reference.
  • 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 Seventh Edition 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. Five new How To boxes to this edition are, "How To: Quickly Figure Out Formal Charge," "How To: Quickly Recognize the Hybridization and Geometry of Atoms," "How To: Quickly Draw and Recognize Enantiomers and Diastereomers," "How To: Retrosynthetically Dissect an Amine into the Proper Starting Materials for a Reductive Amination," and "How To: Recognize Aromatic Compounds: Criteria and Caveats."
  • BIOLOGY CONNECTION: Although still a predominantly synthetic organic chemistry text, the book explicitly links concepts to biological chemistry topics--drawing in biology majors, pre-med 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: With OWL, the #1 online homework and learning system for chemistry, you can improve student learning outcomes. 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 the New MindTap Reader, a fully interactive online e-reader experience that seamlessly integrates authoritative Cengage Learning content, rich media assets, robust note-taking/annotation features and tightly bundled web-apps to create an engaging, holistic student learning environment.

Table of Contents

1. Covalent Bonding and Shapes of Molecules.
2. Alkanes and Cycloalkanes.
3. Stereochemistry and Chirality.
4. Acids and Bases.
5. Alkenes.
Primer I: Reaction Mechanisms
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.
Primer II: Carboxylic Acid Derivative Reaction Mechanisms.
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

  • MCAT PROBLEMS: To better prepare students for the upcoming new MCAT exam, the new edition includes MCAT PRACTICE: PASSAGE AND PROBLEMS throughout the text. First students read the organic chemistry-related essay and then answer a series of multiple-choice questions.
  • NEW PRIMERS: Two new primers (Developing a Reaction Mechanism before Chapter 6 and Carboxylic Acid Derivative Reaction Mechanisms before Chapter 18) set key and possibly difficult concepts apart for easy reference to enhance student understanding.
  • NEWLY-DRAWN ORGANIC CHEMISTRY REACTION ROADMAPS: Creating a cumulative, graphical representation of the different reactions students encounter in the context of important functional groups, the organic chemistry roadmaps help students visualize how to interconvert different functional groups (which often require different reactions from different chapters) by simply identifying the most direct path on the roadmap. New pull‐out cards show the roadmaps in sequential order.
  • REVISED REACTION ROADMAP PROBLEMS: These unique problems relate to the authors' organic chemistry roadmap (see above), which compares organic chemistry to a roadmap, with functional groups analogous to cities and reactions analogous to the roads between them.
  • FIVE NEW "HOW TO" BOXES: Integrated throughout the text at strategic points, the new boxes show students: "How To: Quickly Figure Out Formal Charge," "How To: Quickly Recognize the Hybridization and Geometry of Atoms," "How To: Quickly Draw and Recognize Enantiomers and Diastereomers," "How To: Retrosynthetically Dissect an Amine into the Proper Starting Materials for a Reductive Amination," and "How To: Recognize Aromatic Compounds: Criteria and Caveats."

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.

Bundle: Text, Hybrid + Study Guide with Solutions Manual

ISBN-10: 1305435877 | ISBN-13: 9781305435872

List Price = $433.95  | CengageBrain Price = $433.95  | College Bookstore Wholesale Price = $326.25

This Bundle Includes:

  • Organic Chemistry, Hybrid Edition
    List Price = $217.95  | CengageBrain Price = $217.95  | College Bookstore Wholesale Price = $163.50
  • Study Guide with Solutions Manual
    List Price = $216.95  | CengageBrain Price = $216.95  | College Bookstore Wholesale Price = $162.75


Efficacy and Outcomes

Reviews

"I find that the BFIA text is very sound pedagogically. Essential concepts are carefully and intuitively explained. Take, for example, the essential survival skill of using curved arrow notation and applying this to the understanding or reaction mechanisms. The authors break this skill down into its simplest components and build from there. This starts with the definition of an electron source and an electron sink. From these definitions, students readily grasp the physical driving force behind the flow of electrons in organic reactions in addition to mastering the use of curved arrow notation. The "how to" sections provide an abundance of detail and effectively break traditionally challenging concepts into logical, readily digested portions. Finally, the sections entitled "Chemical Connections" provide very relevant, up-to-date tie-ins of the subject material to matters of chemical, biological and pharmacological interest."

— Patrick Jokiel, The College of New Jersey

"I find the problem set at the end of each chapter superb. I believe this is a culmination of hard work over the years by the authors in this area. His treatment of resonance is quite good but the Organometallics covered in Chapter 24 is also second to none! These are the strongest features of the book."

— Andrew Frazer, University of Central Florida

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

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 = $131.95  | CengageBrain Price = $131.95  | College Bookstore Wholesale Price = $99.25

Study Guide with Solutions Manual  (ISBN-10: 1285052617 | ISBN-13: 9781285052618)

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 Seventh 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 for national standardized tests such as the DAT and MCAT.

List Price = $216.95  | CengageBrain Price = $216.95  | College Bookstore Wholesale Price = $162.75

OWLv2 24-Months Instant Access  (ISBN-10: 1285198972 | ISBN-13: 9781285198972)

Students can use this ISBN to purchase instant access at www.cengagebrain.com to OWL, the #1 online homework and tutorial system for chemistry. With OWL, you'll save time and help your students improve their grades. Developed by chemistry instructors for teaching chemistry, OWL includes powerful course management tools that make homework management a breeze, as well as advanced reporting and grade book features that save you time in grading homework and tracking student progress. With OWL, you can address your students' different learning styles through a wide range of assignment types, including tutorials, visualization exercises, and algorithmically generated homework questions with instant answer-specific feedback. OWL is the only system designed to support mastery learning, allowing students to work at their own pace until they understand each concept and skill. Each time a student tries a problem, OWL changes the chemicals and wording of the question, as well as the numbers, to ensure student mastery. OWL includes the New MindTap Reader, a fully interactive online e-reader experience that seamlessly integrates authoritative Cengage Learning content, rich media assets, robust note-taking/annotation features and tightly bundled web-apps to create an engaging, holistic student learning environment.Visit www.cengage.com/owl to learn more.

List Price = $130.00  | CengageBrain Price = $130.00  | College Bookstore Wholesale Price = $130.00

OWLv2 6-Months Instant Access  (ISBN-10: 1285185846 | ISBN-13: 9781285185842)

Students can use this ISBN to purchase instant access at www.cengagebrain.com to OWL, the #1 online homework and tutorial system for chemistry. With OWL, you'll save time and help your students improve their grades. Developed by chemistry instructors for teaching chemistry, OWL includes powerful course management tools that make homework management a breeze, as well as advanced reporting and grade book features that save you time in grading homework and tracking student progress. With OWL, you can address your students' different learning styles through a wide range of assignment types, including tutorials, simulations , visualization exercises, and algorithmically generated homework questions with instant answer-specific feedback. OWL is the only system designed to support mastery learning, allowing students to work at their own pace until they understand each concept and skill. Each time a student tries a problem, OWL changes the chemicals and wording of the question, as well as the numbers, to ensure student mastery. OWL now includes Quick Prep review assignments that help students learn essential skills to succeed. OWL includes the New MindTap Reader, a fully interactive online e-reader experience that seamlessly integrates authoritative Cengage Learning content, rich media assets, robust note-taking/annotation features and tightly bundled web-apps to create an engaging, holistic student learning environment.Visit www.cengage.com/owl to learn more.

List Price = $100.00  | CengageBrain Price = $100.00  | College Bookstore Wholesale Price = $100.00

Student Supplements

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 = $131.95  | CengageBrain Price = $131.95  | College Bookstore Wholesale Price = $99.25

Study Guide with Solutions Manual  (ISBN-10: 1285052617 | ISBN-13: 9781285052618)

The perfect way to prepare for exams, build problem-solving skills, and get the grade you want! 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 for national standardized tests such as the DAT and MCAT.

List Price = $216.95  | CengageBrain Price = $216.95  | College Bookstore Wholesale Price = $162.75

OWLv2 24-Months Instant Access  (ISBN-10: 1285198972 | ISBN-13: 9781285198972)

Get a better grade in chemistry and 24/7 homework help with OWL, the #1 online homework and tutorial system for chemistry, available for purchase at www.cengagebrain.com. OWL's step-by-step tutorials, visual exercises, and homework questions that provide instant answer-specific feedback help you every step of the way as you master tough chemistry concepts and skills. OWL allows you to learn at your own pace to ensure you've mastered each concept before you move on. OWL includes the New MindTap Reader, a fully interactive online e-reader experience that seamlessly integrates authoritative Cengage Learning content, rich media assets, robust note-taking/annotation features and tightly bundled web-apps to create an engaging, holistic student learning environment. Visit www.cengage.com/owl or talk to your instructor.

List Price = $130.00  | CengageBrain Price = $130.00  | College Bookstore Wholesale Price = $130.00

OWLv2 6-Months Instant Access  (ISBN-10: 1285185846 | ISBN-13: 9781285185842)

Get a better grade in chemistry and 24/7 homework help with OWL, the #1 online homework and tutorial system for chemistry, available for purchase at www.cengagebrain.com. OWL's step-by-step tutorials, visual exercises, and homework questions that provide instant answer-specific feedback help you every step of the way as you master tough chemistry concepts and skills. OWL allows you to learn at your own pace to ensure you've mastered each concept before you move on. OWL includes the New MindTap Reader, a fully interactive online e-reader experience that seamlessly integrates authoritative Cengage Learning content, rich media assets, robust note-taking/annotation features and tightly bundled web-apps to create an engaging, holistic student learning environment. Visit www.cengage.com/owl or talk to your instructor.

List Price = $100.00  | CengageBrain Price = $100.00  | College Bookstore Wholesale Price = $100.00

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.

Brent L. Iverson

Brent L. Iverson received his Ph.D. from the California Institute of Technology. He is a University Distinguished Teaching Professor and the Dean of the School of Undergraduate Studies at University of Texas at Austin, as well as a respected researcher. His research spans the interface of organic chemistry and molecular biology. His group has developed several patented technologies, including an FDA-approved treatment for late-stage anthrax.

Eric Anslyn

Eric Anslyn received his Ph.D. from the California Institute of Technology and is the Norman Hackerman Professor of Chemistry and a University Distinguished Teaching Professor at The University of Texas at Austin. Anslyn's research focuses on the physicals and bioorganic chemistry of synthetic and natural receptors and catalysts.

Christopher S. Foote

Christopher S. Foote was a professor of chemistry at the University of California, Los Angeles. His scholarly credits included Sloan Fellow; Guggenheim Fellow; ACS Baekland Award; ACS Cope Scholar; Southern California Section ACS Tolman Medal; President, American Society for Photobiology; and Senior Editor, Accounts of Chemical Research.