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Organic Chemistry 8th Edition

William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

  • Published
  • Previous Editions 2014
  • 1312 Pages
Starting At 105.00 See pricing and ISBN options


ORGANIC CHEMISTRY is a student-friendly, cutting edge introduction for chemistry, health, and the biological sciences majors. In the Eighth Edition, award-winning authors build on unified mechanistic themes, focused problem-solving, applied pharmaceutical problems and biological examples. Stepwise reaction mechanisms emphasize similarities among mechanisms using four traits: breaking a bond, making a new bond, adding a proton, and taking a proton away. Pull-out organic chemistry reaction roadmaps designed stepwise by chapter help students devise their own reaction pathways. Additional features designed to ensure student success include in-margin highlighted integral concepts, new end-of-chapter study guides, and worked examples. This edition also includes brand new author-created videos. Emphasizing “how-to” skills, this edition is packed with challenging synthesis problems, medicinal chemistry problems, and unique roadmap problems.

William H. Brown, Beloit College

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, University of Texas, Austin

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, University of Texas, Austin

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, University of California, Los Angeles

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.
  • AUTHOR-CREATED VIDEOS: These lessons from the authors, available in the MindTap Reader e-book, take students through the working of almost 100 example problems and important graphics; covering key lessons from the book. The videos provide students with an on-demand resource that covers much of the book’s most difficult and important material.
  • THINGS YOU SHOULD KNOW: Important transitions between distinct topics in the sequence of the book are good places to stop, reflect, and take stock of what has been learned, while looking forward to the next set of chapters. At such transitions, the book includes five primers called “Things You Should Know.” By pulling these key topics out from the chapters, the flow of the chapters is maintained, while emphasizing topics that permeate several future chapters. After reading and fully digesting these primers, students will be well prepared to approach the discipline of organic chemistry including all the material in subsequent chapters.
  • IN-MARGIN HIGHLIGHTED INTEGRAL CONCEPTS: To emphasize that many of the fundamental lessons of organic chemistry continue to guide the discussions of topics in future chapters, the margins now include a series of points derived from the first primer, “Things You Should Know I, General Conclusions from Quantum Mechanics.” These points emphasize that the same fundamental principles of the first primer are used to explain patterns of molecular structure, properties, and reactivity throughout the text.
  • STUDY GUIDES: One of the largest structural changes to the book is a reimagining of the synopsis sections of the chapters into concise, end-of-chapter “Study Guides.” Instead of simply recapping the material, these sections take students through topics with simple bulleted lessons, explanations, and graphic summaries of key reactions related to that topic. Representative end-of-chapter problems are listed for each section, directing students to questions that test their knowledge. Students can carry and refer to these “crib notes” and use them to guide their study when preparing for exams.
  • OWLv2: Almost 200 new end-of-chapter problems have been coded into OWLv2 for the Eighth Edition, and new mechanism activities were added.
  • MCAT PROBLEMS: To better prepare students for the MCAT exam, MCAT PRACTICE: PASSAGE AND QUESTIONS throughout the text have students read an organic chemistry-related essay and then answer a series of multiple-choice questions.
  • 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 end-of-chapter problems apply organic chemistry to medicinal chemistry and the pharmaceutical sciences.
  • 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.
  • OWLv2 INTEGRATION: OWLv2 is the most trusted online learning solution for chemistry. Featuring chemist-developed content, OWLv2 is the only system designed to elevate thinking through Mastery Learning, allowing students to work at their own pace until they understand each concept and skill. Each time a student tries a problem, OWLv2 changes the chemistry, values, and sometimes the wording of the question to ensure students are learning the concepts. With detailed, instant feedback, improved student and instructor tools, and greater functionality, OWLv2 is more robust than ever.
  • 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 are broken into multiple 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. “Things You Should Know III, Reaction Mechanisms,” sets this explanation apart for easy reference.
  • ORGANIC CHEMISTRY REACTION ROADMAPS: Creating a cumulative, graphical representation of the different reactions students encounter in the context of important functional groups, organic chemistry roadmap inserts 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. Unique end-of-chapter problems relate to the authors' organic chemistry roadmap.
  • IN-CHAPTER WORKED EXAMPLES: Featuring a pedagogy normally reserved for general chemistry texts, the book offers worked examples 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.
  • "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.
1. Covalent Bonding and Shapes of Molecules.
Things You Should Know I: General Conclusions from Quantum Mechanics.
2. Alkanes and Cycloalkanes.
3. Stereochemistry and Chirality.
4. Acids and Bases.
5. Alkenes.
Things You Should Know II: Nucleophiles and Electrophiles.
Things You Should Know III: Reaction Mechanisms.
6. Reactions of Alkenes.
7. Alkynes.
8. Haloalkanes, Halogenation, and Radical Reactions.
Things You Should Know IV: Common Mistakes in Arrow Pushing.
9. Nucleophilic Substitution and β -Elimination.
10. Alcohols.
11. Ethers, Epoxides, and Sulfides.
12. Infrared Spectroscopy.
13. Nuclear Magnetic Resonance Spectroscopy.
14. Mass Spectrometry.
15. Introduction to Organometallic Compounds.
16. Aldehydes and Ketones.
17. Carboxylic Acids.
Things You Should Know V: 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.
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 Infrared Absorption Frequencies.
7. Electrostatic Potential Maps.
8. Summary of Stereochemical Terms.
9. Summary of the Rules of Nomenclature.
10. Organic Chemistry Reaction Roadmaps.
Glossary G-1.
Index I-1.
OWLv2 offers a full, mobile-ready textbook combined with mastery learning activities that allow students to understand each concept and skill at their own pace.

This Cengage solution can be seamlessly integrated into most Learning Management Systems (Blackboard, Brightspace by D2L, Canvas, Moodle, and more) but does require a different ISBN for access codes. Please work with your Cengage Learning Consultant to ensure the proper course set up and ordering information. For additional information, please visit the LMS Integration site.

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Cengage provides a range of supplements that are updated in coordination with the main title selection. For more information about these supplements, contact your Learning Consultant.


Instructor Resource Website

ISBN: 9781305865372
Everything you need for your course in one place! This collection of book-specific lecture and class tools is available online via Access and download PowerPoint presentations, images, instructor’s manual, videos, and more.

Student Study Guide and Solutions Manual

ISBN: 9781305864504
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 Eighth 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.

Cengage Learning Testing, powered by Cognero® Instant Access

ISBN: 9781305672550
Cengage Learning Testing, powered by Cognero® is a flexible, online system that allows you to author, edit, and manage test bank content from multiple Cengage Learning solutions, create multiple test versions in an instant, and deliver tests from your LMS, your classroom or wherever you want.


Student Study Guide and Solutions Manual

ISBN: 9781305864504
Prepare for exams, build problem-solving skills, and get the grade you want with this comprehensive guide! Offering detailed solutions to all in-text and end-of-chapter problems, this guide helps you achieve a deeper intuitive understanding of chapter material through constant reinforcement and practice. As a result, you’ll be much better prepared for in-class quizzes and tests, as well as for national standardized tests such as the DAT and MCAT.

Pushing Electrons

ISBN: 9781133951889
This brief guidebook assists you in mastering the difficult concept of pushing electrons that is vital to your success in Organic Chemistry. With an investment of only 12 to 16 hours of self-study you can have a better understanding of how to write resonance structures and will become comfortable with bond-making and bond-breaking steps in organic mechanisms. A paper-on-pencil approach uses active involvement and repetition to teach you to properly push electrons to generate resonance structures and write organic mechanisms with a minimum of memorization. Compatible with any organic chemistry textbook.

Chemical Principles for Organic Chemistry

ISBN: 9781285457697
Covering all the concepts that carry over from general chemistry to the organic course CHEMICAL PRINCIPLES FOR ORGANIC CHEMISTRY helps you "unlearn" some of the approaches you learned in General Chemistry, learn new or different ones, and successfully apply concepts from General Chemistry to organic chemistry.

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