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Overview

The most trusted and best-selling text for organic chemistry just got better! Updated with more coverage of nuclear magnetic resonance spectroscopy, expanded with new end-of-chapter mechanism problems and Practice Your Scientific Reasoning and Analysis questions, and enhanced with OWLv2, the latest version of the leading online homework and learning system for chemistry, John McMurry's ORGANIC CHEMISTRY continues to set the standard for the course. The Ninth Edition also retains McMurry's hallmark qualities: comprehensive, authoritative, and clear. McMurry has developed a reputation for crafting precise and accessible texts that speak to the needs of instructors and students. More than a million students worldwide from a full range of universities have mastered organic chemistry through his trademark style, while instructors at hundreds of colleges and universities have praised his approach time and time again. 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.

John E. McMurry, Cornell University

John E. McMurry received his B.A. from Harvard University and his Ph.D. at Columbia University. He is a Fellow of the American Association for the Advancement of Science, and an Alfred P. Sloan Research Foundation Fellow. He has received several awards, which include the National Institutes of Health Career Development Award, the Alexander von Humboldt Senior Scientist Award, and the Max Planck Research Award. In addition to ORGANIC CHEMISTRY, he is also the author or coauthor of ORGANIC CHEMISTRY: A BIOLOGICAL APPROACH, FUNDAMENTALS OF ORGANIC CHEMISTRY, THE ORGANIC CHEMISTRY OF BIOLOGICAL PATHWAYS.
  • Expanded discussions of interpreting mass spectra, with new spectroscopy problems throughout the book.
  • Reorganized and expanded discussion of the theory of nuclear magnetic resonance, and interpretation of NMR data, with new NMR problems.
  • Why This Chapter now precedes the introduction in each chapter, immediately setting the context for what to expect.
  • NEW! Seven Practice Your Scientific Analysis and Reasoning essays and corresponding questions are modeled after professional exams such as the MCAT. Topics focus on the latest developments in the medical, pharmaceutical or biological application of organic chemistry.
  • Seven new Practice Your Scientific Analysis and Reasoning features have been added in key places throughout the book, with practice questions suitable for professional exam preparation such as the MCAT.
  • Chapter 2—Polar Covalent Bonds: Acids and Bases. Formal change figures for greater accuracy. New mechanism problems have been added at the end of the chapter.
  • Chapter 3—Alkanes and Their Stereochemistry. Figures and steps for naming alkanes have been revised based on user feedback.
  • Chapter 6—An Overview of Organic Reactions. New problems have been added to the end of the chapter including new reaction mechanism problems.
  • Chapter 7—Alkenes: Structure and Reactivity. Alkene Stereochemistry has been updated with expanded examples for practicing E and Z geometry. A new end-of-chapter Something Extra examining terpenes has been added. Additional practice problems on mechanisms have been added to the end of the chapter.
  • Chapter 8—Alkenes: Reactions and Synthesis. New mechanism practice problems have been added at the end of the chapter. A new Something Extra feature on natural rubber has been added.
  • Chapter 9—Alkynes: An Introduction to Organic Synthesis. Sections on alkyne nomenclature and reactions of alkynes has been updated for greater accuracy. New mechanism problems have been added to the end of the chapter.
  • Chapter 10—Organohalides. Suzuki-Miyaura reactions, curved arrow drawing, and electron pushing mechanisms are emphasized in new problems at the end of the chapter.
  • Chapter 11—Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations. There are nine additional end-of-chapter problems, with particular focus on elimination reaction mechanisms.
  • Mechanism problems at the ends of chapters are now grouped together so that they are easily located and recognized.
  • Chapter 12—Structure Determination: Mass Spectrometry and Infrared Spectroscopy. Expanded discussion of interpreting mass spectra, additional examples, and new problems.
  • Chapter 13— Structure Determination: Nuclear Magnetic Resonance Spectroscopy. Discussions of the theory of nuclear magnetic resonance and the interpretation of NMR data have been expanded and reorganized, and new NMR problems have been added.
  • Chapter 14— Conjugated Compounds and Ultraviolet Spectroscopy. New problems have been added to the end of the chapter, including six new mechanism problems.
  • Chapter 15—Benzene and Aromaticity. The discussion of spectroscopic characterization of benzene derivatives has been expanded. New mechanism and spectroscopy problems have been added to the end of the chapter.
  • Chapter 16—Chemistry of Benzene: Electrophilic Aromatic Substitution. New problems have been added to the end of the chapter, including mechanism practice problems.
  • Chapter 17--Alcohols and Phenols. New spectroscopy examples and problems have been added, along with new mechanism problems at the end of the chapter.
  • Chapter 18—Ethers and Epoxides; Thiols and Sulfides. New spectroscopy examples and problems have been added, along with new mechanism problems at the end of the chapter.
  • Chapter 19—Aldehydes and Ketones: Nucleophilic Addition Reactions. The discussion of IR and 
NMR of aldehydes/ketones has been expanded. New NMR problems and mechanism practice 
problems have been added).
  • Chapter 20—Carboxylic Acids and Nitriles. The discussion of IR and NMR of carboxylic acid has 
been updated. New problems have been added to the end of the chapter, including mechanism 
and spectroscopy problems).
  • Chapter 21—Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions. The discussion 
of electronic effects in IR and NMR of carboxylic acid derivatives has been expanded with two 
new problems). New mechanism problems have also been added to the end of the chapter.
  • Many new problems at the ends of chapters have been added, including 108 new mechanism- drawing practice problems and new spectroscopy and NMR problems.
  • Chapter 22 and Chapter 23—Carbonyl Alpha-Substitution Reactions; Carbonyl Condensation 
Reactions. New problems have been added to the end of the chapter, including additional 
mechanism practice problems).
  • Chapter 24—Amines and Heterocycles. The discussion of IR and NMR of amines has been updated, 
and new spectroscopy and mechanism practice problems have been added to the end of the chapter.
  • Chapter 25—Biomolecules: Carbohydrates. Expanded the coverage of other important 
carbohydrates and revised worked examples related to drawing Fischer projections).
  • Chapter 26—Biomolecules: Amino Acids, Peptides, and Proteins. Revised and updated the 
Something Extra feature on the Protein Data Bank to make it more current).
  • Chapter 28—Biomolecules: Nucleic Acids. Updated and revised content on DNA sequencing and 
DNA synthesis).
  • Deeper Look features have been changed to Something Extra, with updated coverage on each topic.
  • HOLISTIC OVERVIEWS. At two key points, McMurry provides an "Overview" to help students grasp the subject matter more holistically. The first "Overview" offers a review of organic mechanisms, while the second discusses the cohesiveness of carbonyl group reactions.
  • AN EXEMPLARY ARRAY OF 1,800 PROBLEMS. McMurry's extensive end-of-chapter problem sets provide students with ample opportunity to practice and master their organic chemistry problem-solving skills.
  • PROBLEM-SOLVING FOCUS. Each chapter contains many worked out examples with "Strategy Statements" that illustrate how to solve problems. Each practice problem and solution is then followed by a similar problem for the student to solve. This provides immediate problem-solving reinforcement for the student.
  • UNIQUE COVERAGE. McMurry emphasizes organic synthesis as a teaching device to help students organize and work with the large body of factual information that makes up organic chemistry. He also offers an unusually complete treatment of the organic chemistry of nucleic acids and an integrated treatment of polymer chemistry.
  • VERTICAL FORMAT FOR REACTION MECHANISMS. McMurry's hallmark vertical format is used to explain reaction mechanisms. The mechanisms are printed vertically while explanations of the changes taking place in each step are printed next to the reaction arrow. This allows students to easily see what is occurring at each step in a reaction without having to jump back and forth between the text and structures.
  • 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 even the wording of the question to ensure students are learning the concepts and not cheating the system. With detailed, instant feedback and interactive learning resources, students get the help they need when they need it. Now with improved student and instructor tools and greater functionality, OWLv2 is more robust than ever. Discover the power of OWLv2 and take learning to a higher level.
  • IMPROVED CHAPTER-ENDING PROBLEM ORGANIZATION. End-of-chapter problems are now grouped by type to assist professors in assigning problems and students in solving them. Mechanism-type problems have now been given their own section in chapters containing mechanism problems.
  • UNIQUE "VISUALIZING CHEMISTRY" PROBLEMS. These problems challenge students to make the essential connection between typical line-bond drawings and computer-generated molecular models. "Visualizing Chemistry" problems enhance your students' ability to bridge the gap between the microscopic level of molecules and the macroscopic level of daily life.
1. Structure and Bonding.
2. Polar Covalent Bonds; Acids and Bases.
3. Organic Compounds: Alkanes and Their Stereochemistry.
4. Organic Compounds: Cycloalkanes and Their Stereochemistry
5. Stereochemistry at Tetrahedral Centers.
6. An Overview of Organic Reactions.
7. Alkenes: Structure and Reactivity.
Practice Your Scientific Analysis and Reasoning I: The Chiral Drug Thalidomide
8. Alkenes: Reactions and Synthesis.
9. Alkynes: An Introduction to Organic Synthesis.
10. Organohalides.
11. Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations.
Practice Your Scientific Analysis and Reasoning II: From Mustard Gas to Alkylating Anticancer Drugs
12. Structure Determination: Mass Spectrometry and Infrared Spectroscopy.
13. Structure Determination: Nuclear Magnetic Resonance Spectroscopy.
14. Conjugated Compounds and Ultraviolet Spectroscopy.
15. Benzene and Aromaticity.
Practice Your Scientific Analysis and Reasoning III: Photodynamic Therapy (PDT)
16. Chemistry of Benzene: Electrophilic Aromatic Substitution.
17. Alcohols and Phenols.
18. Ethers and Epoxides; Thiols and Sulfides.
Preview of Carbonyl Chemistry.
19. Aldehydes and Ketones: Nucleophilic Addition Reactions.
Practice Your Scientific Analysis and Reasoning IV: SSRIs
20. Carboxylic Acids and Nitriles.
21. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions.
22. Carbonyl Alpha-Substitution Reactions.
23. Carbonyl Condensation Reactions.
Practice Your Scientific Analysis and Reasoning V: Thymine in DNA
24. Amines and Heterocycles.
25. Biomolecules: Carbohydrates.
26. Biomolecules: Amino Acids, Peptides, and Proteins.
Practice Your Scientific Analysis and Reasoning VI: Melatonin and Serotonin
27. Biomolecules: Lipids.
28. Biomolecules: Nucleic Acids.
29. The Organic Chemistry of Metabolic Pathways.
30. Orbitals and Organic Chemistry: Pericyclic Reactions.
31. Synthetic Polymers.
Practice Your Scientific Analysis and Reasoning VII: The Potent Antibiotic of Endiandric Acid C.
OWLv2
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.

Standalone Digital Access — Ultimate Value

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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.

FOR INSTRUCTORS

Cengage Learning Testing, powered by Cognero® Instant Access

ISBN: 9781305279940
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; deliver tests from your LMS, your classroom or wherever you want.

Study Guide with Student Solutions Manual

ISBN: 9781305082144
Help your students study more effectively and improve thir performance at exam time with this comprehensive guide! Written by Susan McMurry, the Study Guide and Solutions Manual provide answers and explanations to all in-text and end-of-chapter exercises. Content has been updated to match the new in-text and end-of-chapter exercises.

FOR STUDENTS

Study Guide with Student Solutions Manual

ISBN: 9781305082144
Study more effectively and improve your performance at exam time with this comprehensive guide! Written by Susan McMurry, the Study Guide and Solutions Manual provide answers and explanations to all in-text and end-of-chapter exercises. Content has been updated to match the new in-text and end-of-chapter exercises.