Organic Chemistry,
8th Edition

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.
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 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.

• 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 is the Warren J. and Viola Mae Raymer Professor, a University Distinguished Teaching Professor and the dean of the School of Undergraduate Studies at The University of Texas at Austin. 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 California Institute of Technology. He is the Welch Regents Chair of Chemistry and a University Distinguished Teaching Professor at The University of Texas at Austin, as well as an HHMI Professor. His research focuses on the physical 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.

• 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.

• 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.

• 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.

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