Higher Education

Organic Chemistry: With Biological Applications, 2nd Edition

  • John E. McMurry Cornell University
  • ISBN-10: 0495391441  |  ISBN-13: 9780495391449
  • 1152 Pages
  • Previous Editions: 2007
  • © 2011 | Published
  • College Bookstore Wholesale Price = $309.00
  • Newer Edition Available
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Renowned for its student-friendly writing style and fresh perspective, this fully updated Second Edition of John McMurry's ORGANIC CHEMISTRY WITH BIOLOGICAL APPLICATIONS provides full coverage of the foundations of organic chemistry—enhanced by biological examples throughout. Based on user feedback, McMurry continues to discuss the organic chemistry of biological pathways and now adds two dozen additional organic chemistry topics, as well as new problems, new illustrations, and new essays. Media integration with OWL for Organic Chemistry, a customizable online learning system and assessment tool, reduces faculty workload, facilitates instruction, and helps students master concepts through tutorials, simulations, and algorithmically generated homework questions.

Features and Benefits

  • VERTICAL FORMAT FOR CHEMICAL AND BIOCHEMICAL REACTION MECHANISMS. John McMurry's hallmark vertical format for mechanisms prints action steps vertically and explains changes taking place in each step next to the reaction arrows so students can see what is occurring at each step in a reaction without having to jump back and forth between the text and structures.
  • VISUALIZATION OF BIOLOGICAL REACTIONS. McMurry "ghosts" the non-reacting parts of biological reactions to focus student attention on the reacting parts in large molecules, so they can more easily visualize changes that occur during reactions of large biomolecules.
  • "WHY THIS CHAPTER?" INTRODUCTIONS. A brief paragraph in each chapter introduction tells students why the material about to be covered is important and explains how the organic chemistry in each chapter relates to biological chemistry.
  • TITLES FOR EACH WORKED EXAMPLE. The worked examples in each chapter are titled to give students a frame of reference and each includes a strategy and worked-out solution, followed by problems for students to try on their own.
  • LAGNIAPPES ("SOMETHING EXTRA"). McMurry's chapter-ending "Lagniappes" relate real-world concepts to students' lives through essays.

Table of Contents

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 and Alkynes.
8. Reactions of Alkenes and Alkynes.
9. Aromatic Compounds.
10. Structure Determination: Mass Spectrometry, Infrared Spectroscopy,
and Ultraviolet Spectroscopy.
11. Structure Determination: Nuclear Magnetic Resonance Spectroscopy.
12. Organohalides: Nucleophilic Substitutions and Eliminations.
13. Alcohols, Phenols, and Thiols; Ethers and Sulfides.
14. Aldehydes and Ketones: Nucleophilic Addition Reactions.
15. Carboxylic Acids and Nitriles.
16. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions.
17. Carbonyl Alpha-Substitution and Condensation Reactions.
18. Amines and Heterocycles.
19. Biomolecules: Amino Acids, Peptides, and Proteins.
20. Amino Acid Metabolism.
21. Biomolecules: Carbohydrates.
22. Carbohydrate Metabolism.
23. Biomolecules: Lipids and Their Metabolism.
24. Biomolecules: Nucleic Acids and Their Metabolism.
25. Secondary Metabolites: An Introduction to Natural Products Chemistry.

What's New

  • A NEW BOOK TITLE. The new title emphasizes that this Second Edition is a mainstream organic chemistry text written for the standard organic chemistry course taught in colleges and universities throughout the world.
  • EARLIER COVERAGE OF STEREOCHEMISTRY AND SPECTROSCOPY. Based on user feedback, the chapter on chirality and stereochemistry at tetrahedral centers, a topic crucial to understanding biological chemistry, now appears much earlier in the book (Chapter 5), and the chapters on spectroscopy now precede the chapter on organohalides.
  • ENHANCED PROBLEMS, EXAMPLES, ILLUSTRATIONS, & ESSAYS. To enhance problem-solving and visualization skills, McMurry increases the number of multi-step problems and reduces the number of drill-type problems, increases the use of electrostatic potential maps that illustrate structure and reactivity, includes at least one MCAT worked example in every chapter, and includes new Green Chemistry essays.
  • SIMPLIFIED COVERAGE. Based on user feedback, McMurry offers simplified coverage of amino acid metabolism, amino acid biosynthesis, nucleotide metabolism, and nucleotide biosynthesis.
  • ADDITIONAL ORGANIC CHEMISTRY TOPICS: McMurry adds new coverage of: alkene ozonolysis and diol cleavage, carbenes to alkenes, the Diels–Alder cycloaddition reaction, acetylide alkylations (8); aromatic ions, nucleophilic aromatic substitution, aromatic hydrogenation (9); allylic bromination of alkenes (12); Dess–Martin oxidation of alcohols, protection of alcohols as silyl ethers, Claisen rearrangement (13); protection of ketones, aldehydes as acetals, conjugate addition of diorganocuprates to enones (14); Grignard reaction of nitriles (15); reduction of acid halides, Grignard reaction of acid halides, reaction of diorganocuprates with acid halides (16); and alpha bromination of carboxylic acids (17).

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 + Study Guide with Solutions Manual

ISBN-10: 0495787256  | ISBN-13: 9780495787259

List Price = $570.95  | CengageBrain Price = $570.95  | College Bookstore Wholesale Price = $429.00

This Bundle Includes:

  • Organic Chemistry: With Biological Applications
    List Price = $411.95  | CengageBrain Price = $411.95  | College Bookstore Wholesale Price = $309.00
  • Study Guide with Solutions Manual
    List Price = $159.95  | CengageBrain Price = $159.95  | College Bookstore Wholesale Price = $120.00

Bundle: Organic Chemistry: A Guided Inquiry, 2nd + Organic Chemistry: With Biological Applications, 2nd

ISBN-10:  113316675X | ISBN-13:  9781133166757

List Price = $541.95  | CengageBrain Price = $541.95  | College Bookstore Wholesale Price = $407.25

This Bundle Includes:

  • Organic Chemistry: A Guided Inquiry
    List Price = $130.95  | CengageBrain Price = $130.95  | College Bookstore Wholesale Price = $98.25
  • Organic Chemistry: With Biological Applications
    List Price = $411.95  | CengageBrain Price = $411.95  | College Bookstore Wholesale Price = $309.00


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

Test Bank on eBank  (ISBN-10: 0495391492 | ISBN-13: 9780495391494)

PowerLecture™ with ExamView® and JoinIn™  (ISBN-10: 0495391468 | ISBN-13: 9780495391463)

PowerLecture with ExamView® and JoinIn™ Instructor's CD/DVD-ROM INSTRUCTOR DESCRIPTION: 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 by Richard Morrison, University of Georgia, 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 sample chapters from the Student Solutions Manual and Study Guide. PowerLecture includes the Chemistry Multimedia Library DVD-ROM, which contains animations, simulations, and movies for all Chemistry subjects, oganized by topic for lecture presentations.

Student Supplements

Study Guide with Solutions Manual  (ISBN-10: 049539145X | ISBN-13: 9780495391456)

This Study Guide and Solutions Manual provide answers and explanations to all in-text and end-of-chapter exercises.

List Price = $159.95  | CengageBrain Price = $159.95  | College Bookstore Wholesale Price = $120.00

Meet the Author

Author Bio

John E. McMurry

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.