Higher Education

Organic Chemistry: With Biological Applications, Hybrid Edition, 3rd Edition

  • Includes OWL Printed Access Card.
  • John E. McMurry Cornell University
  • ISBN-10: 128586784X  |  ISBN-13: 9781285867847
  • 992 Pages
  • © 2015 | Published
  • College Bookstore Wholesale Price = $144.25

About

Overview

Renowned for its student-friendly writing style and fresh perspective, this fully updated Third Edition of John McMurry's ORGANIC CHEMISTRY WITH BIOLOGICAL APPLICATIONS provides full coverage of the foundations of organic chemistry--enhanced by biological examples throughout. In addition, McMurry discusses the organic chemistry behind biological pathways. New problems, illustrations, and essays have been added. 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. 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

  • EARLIER COVERAGE OF STEREOCHEMISTRY AND SPECTROSCOPY. Chirality and stereochemistry at tetrahedral centers, a topic crucial to understanding biological chemistry, appears early in Chapter 5.
  • ENHANCED PROBLEMS. To enhance problem-solving and visualization skills, McMurry uses many multi-step problems and reduces the number of drill-type problems.
  • VERTICAL FORMAT FOR CHEMICAL AND BIOCHEMICAL REACTION MECHANISMS. Mechanisms are printed with action steps vertically, alongside annotations for each step next, 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.
  • WORKED EXAMPLES. 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.
  • PREVIEW OF CARBONYL CHEMISTRY. Following Chapter 13, there is an interchapter that highlights the idea that studying organic chemistry works by both summarizing past ideas and looking ahead to new ones.
  • SOMETHING EXTRA boxes. McMurry's chapter-ending boxes relate real-world concepts to chemistry through essays.
  • HELPFUL LEARNING AIDS. End-of-chapter summaries and key words help students focus on the key concepts in a chapter. Reaction Summaries bring together the key reactions from that chapter into one complete list.
  • Improve student learning outcomes with OWLv2, the #1 online homework and learning system for chemistry, now with new features and enhanced functionality! Developed by chemistry instructors, OWLv2's reporting and grade book features simplify homework management and track student progress. OWLv2 addresses different student learning styles through tutorials, visualization exercises, and algorithmically generated homework questions with instant answer-specific feedback. With OWLv2's mastery learning approach, students work at their own pace until they understand each concept/skill. OWL includes MindTap Reader™, an iPad-compatible multimedia eBook. Gen Chemistry, GOB, and Liberal Arts courses include Quick Prep modules to help students learn essential skills.

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: A Preview of Carbonyl Chemistry
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.
e25. Secondary Metabolites: An Introduction to Natural Products Chemistry.
e26. Orbitals and Organic Chemistry: Pericyclic Reactions.
e27. Synthetic Polymers.

What's New

  • WHY THIS CHAPTER? now begins each chapter; it is a brief introduction about the material being covered, why it is important and how the organic chemistry in the chapter relates to biological chemistry.
  • Figure and table references in the text are now in color to help reference them. All figure legends now begin with a boldface title to help students easily identify their content.
  • SOMETHING EXTRA essays end each chapter and tie the chapter content to relevant real-world material. Some new essays include, "Organic Foods," and "Dental Anesthetics."
  • Many new problems have been included at the end of chapters.
  • Some new content includes: Mercury-catalyzed alkyne hydration (Chapter 8); Enols and tautomerization (Chapter 8); Conversion of alcohols to alkyl fluorides (Chapter 12); Organic coupling reactions (Chapter 12); Base-induced epoxide cleavage (Chapter 13); Killiani-Fischer and Whol degradation (Chapter 21); Prostaglandins and other eicosanoids (Chapter 23).
  • An increase in the number of Organic OWL questions for the online homework system.
  • The #1 online homework and learning system for chemistry, OWLv2, is available for this text--now with new instructor features and enhanced functionality: a Dashboard that consolidates all course materials; easy, intuitive assignment creation and management; ability to preview and select activities/questions for each assignment; new assignment settings and options; improved gradebook; Personalized Study tools to help students focus their time on the key concepts and skills; and MindTap Reader™, a new eBook with apps and embedded video. OWLv2 courses for Gen Chem, GOB, Organic, and Liberal Arts now include Quick Prep essential skills assignments that can be taken before the semester begins or during the first few weeks, to help students succeed in the course. For this course, OWLv2 also includes new interactive versions of the end-of-chapter questions from the text and new iPad-compatible visualizations and tutorials.

Efficacy and Outcomes

Reviews

"I find it superior at providing a better bridge to biochemistry with its in-depth discussions at the end of the text as well as the integration of biological and biochemical issues throughout the text. I really appreciate the text's integration of biochemical concepts. It does a really nice job at explaining the organic chemistry basis of many biochemical reactions. Many students who take this course are in the pre-health programs, and biochemistry is highly recommended. The book will serve the student well at assisting him/her to better understand the chemistry behind biology."

— Peter Bell, Tarleton State University

"The book is excellent. I think Professor McMurry took a real chance in writing a book that was so different from the texts considered to be mainstream, such as the books by Carey or Solomons."

— William Lavell, Camden County College

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

Online PowerLecture with Cognero and JoinIn™ Student Response System  (ISBN-10: 1305087984 | ISBN-13: 9781305087989)

Search for this text at login.CENGAGE.com and choose Instructor Companion Site to access these digital resources for this text: 1) PowerPoint® lecture slides by Richard Morrison of the University of Georgia, Athens; 2) Image libraries for figures, photographs, and numbered tables; 3) Sample chapters from the Student Solutions Manual and Study Guide. 4) List of end-of-chapter questions that you can assign in OWLv2; 5) Cognero® online testing software with questions by Scott Lefler, Arizona State University 5) "Clicker" content for use with the classroom response system of your choice; 6) Chemistry Multimedia Library of lecture-ready animations, simulations, and movies.

Study Guide with Solutions Manual  (ISBN-10: 1305087976 | ISBN-13: 9781305087972)

Written by Susan McMurry, the Study Guide and Solutions Manual provide answers and explanations to all in-text and end-of-chapter exercises, and include supplemental information via appendices. This print text doubles as an Instructor Solutions Manual. Three preview chapters are provided on the companion site.

List Price = $159.95  | CengageBrain Price = $159.95  | College Bookstore Wholesale Price = $120.50

OWLv2 6-Months Instant Access  (ISBN-10: 1305081382 | ISBN-13: 9781305081383)

Students can use this ISBN at www.CENGAGEbrain.com to purchase instant access to OWLv2, the #1 online solution for chemistry, now with new features and enhanced functionality. OWLv2 includes powerful course management tools and advanced reporting and grade book features to track student progress. OWLv2 addresses different learning styles through a range of assignment types like algorithmically generated problems with instant answer-specific feedback--and it's easier to use. With OWLv2's mastery learning approach, students work at their own pace until they understand each concept and skill. Each time a student tries a problem, OWLv2 changes the variables to ensure student mastery and help prevent students "gaming" the system. OWLv2 includes MindTap Reader™, a new iPad-compatible multimedia eBook. OWLv2 for Gen Chem, GOB, and Liberal Arts includes Quick Prep essential skills assignments. Visit www.CENGAGE.com/owl to learn more.

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

OWLv2, 4 terms (24 months) Instant Access  (ISBN-10: 1305081390 | ISBN-13: 9781305081390)

Students can use this ISBN at www.CENGAGEbrain.com to purchase instant access to OWLv2, the #1 online solution for chemistry, now with new features and enhanced functionality. OWLv2 includes powerful course management tools and advanced reporting and grade book features to track student progress. OWLv2 addresses different learning styles through a range of assignment types like algorithmically generated problems with instant answer-specific feedback--and it's easier to use. With OWLv2's mastery learning approach, students work at their own pace until they understand each concept and skill. Each time a student tries a problem, OWLv2 changes the variables to ensure student mastery and help prevent students "gaming" the system. OWLv2 includes MindTap Reader™, a new iPad-compatible multimedia eBook. OWLv2 for Gen Chem, GOB, and Liberal Arts includes Quick Prep essential skills assignments. Visit www.CENGAGE.com/owl to learn more.

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

OWLv2 with Student Solutions Manual, 4 terms (24 months) Instant Access  (ISBN-10: 130508800X | ISBN-13: 9781305088009)

Students can use this ISBN to purchase instant access at www.CENGAGEbrain.com to the eBook for the Student Solutions Manual. Written by Susan McMurry, the Study Guide and Solutions Manual provide answers and explanations to all in-text and end-of-chapter exercises, and include supplemental information via appendices. This is the eBook version of the print which can also be used as the Instructor's Manual.

List Price = $52.00  | CengageBrain Price = $52.00  | College Bookstore Wholesale Price = $52.00

OWLv2 6-Months LabSkills PreLabs for Organic Chemistry Instant Access  (ISBN-10: 1285431723 | ISBN-13: 9781285431727)

Are your students ready for Lab? Student can use this ISBN to purchase instant access at www.CENGAGEbrain.com to the new LabSkills course powered by OWLv2, the #1 online homework and tutorial system for chemistry. LabSkills prepares students for lab through automatically graded prelab assignments and makes it easy for you to assign the material for students to complete before lab. Launched in the UK, LabSkills is used by schools and universities in more than thirty countries worldwide. LabSkills includes step-by-step videos to introduce students to lab techniques, equipment and safety skills; interactive modules that allow students interact with lab equipment prior to lab; safety training and information to ensure that students are prepared to safely complete their labs; and quizzes to assess student understanding and retention of key concepts. To learn more or to see a demo, please contact your CENGAGE Learning representative or visit us at www.CENGAGE.com/owl.

List Price = $54.00  | CengageBrain Price = $54.00  | College Bookstore Wholesale Price = $54.00

OWLv2 LabSkills PreLabs for Organic Chemistry, 4 terms (24 months) Instant Access  (ISBN-10: 1285431715 | ISBN-13: 9781285431710)

Are your students ready for Lab? Student can use this ISBN to purchase instant access at www.CENGAGEbrain.com to the new LabSkills course powered by OWLv2, the #1 online homework and tutorial system for chemistry. LabSkills prepares students for lab through automatically graded prelab assignments and makes it easy for you to assign the material for students to complete before lab. Launched in the UK, LabSkills is used by schools and universities in more than thirty countries worldwide. LabSkills includes step-by-step videos to introduce students to lab techniques, equipment and safety skills; interactive modules that allow students interact with lab equipment prior to lab; safety training and information to ensure that students are prepared to safely complete their labs; and quizzes to assess student understanding and retention of key concepts. To learn more or to see a demo, please contact your CENGAGE Learning representative or visit us at www.CENGAGE.com/owl.

List Price = $61.00  | CengageBrain Price = $61.00  | College Bookstore Wholesale Price = $61.00

LMS Integrated for OWLv2 with MindTap Reader, 4 terms (24 months) Instant Access  (ISBN-10: 130539870X | ISBN-13: 9781305398702)

MindLinks is a new service provided by Cengage to allow for deeper integration of Cengage’s digital suite, including the OWLv2 product, into an institution’s Learning Management System (LMS). The service works by using portable links that allow two-way communication between a Learning Management System and a Cengage digital product. Cengage developed MindLinks to work with all major Learning Management Systems to expand functionality. For more information on MindLinks, contact mindlinks@cengage.com.

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

SpartanModel Electronic Modeling Kit  (ISBN-10: 0495017930 | ISBN-13: 9780495017936)

SpartanModel replaces the plastic models used by past generations of organic chemistry students. A set of easy-to-use builders allow for the construction and 3-D manipulation of molecules of any size or complexity. Each copy includes the software on CD ROM, an extensive molecular database, 3-D glasses, and the Tutorial and Users Guide with 50 pages of activities for organic chemistry.

List Price = $117.95  | CengageBrain Price = $117.95  | College Bookstore Wholesale Price = $89.00

Maruzen International Organic Modeling Kit #1013  (ISBN-10: 0840053258 | ISBN-13: 9780840053251)

Help your students understand not only molecular structures, but also atom hybrid orbitals, bond angle, and bond length with the MARUZEN INTERNATIONAL ORGANIC MODELING KIT #1013, designed in consultation with Cengage Learning. This modeling kit can be packaged with any Cengage Learning organic chemistry text at a discounted price.

List Price = $34.95  | College Bookstore Wholesale Price = $26.00

Student Supplements

Study Guide with Solutions Manual  (ISBN-10: 1305087976 | ISBN-13: 9781305087972)

This Study Guide and Solutions Manual provide answers and explanations to all in-text and end-of-chapter exercises and include supplemental information to help enrich your chemistry experience.

List Price = $159.95  | CengageBrain Price = $159.95  | College Bookstore Wholesale Price = $120.50

OWLv2 6-Months Instant Access  (ISBN-10: 1305081382 | ISBN-13: 9781305081383)

If your instructor requires OWLv2 for this course, you can use this ISBN to purchase instant access at www.CENGAGEbrain.com. OWLv2 is the #1 online homework and learning system for chemistry, proven to help you get a better grade in chemistry and available 24/7. OWLv2 has graded tutorials, visual exercises, and homework questions. You'll get instant answer-specific feedback to help you every step of the way as you master tough chemistry concepts and skills. OWLv2 allows you to learn at your own pace to ensure you've mastered each concept before you move on. OWLv2 includes an iPad-compatible digital textbook available online 24/7, enhanced with apps and embedded video, and activities for a seamless learning experience. To learn more, visit www.CENGAGE.com/owl or talk to your instructor.

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

OWLv2, 4 terms (24 months) Instant Access  (ISBN-10: 1305081390 | ISBN-13: 9781305081390)

If your instructor requires OWLv2 for this course, you can use this ISBN to purchase instant access at www.CENGAGEbrain.com. OWLv2 is the #1 online homework and learning system for chemistry, proven to help you get a better grade in chemistry and available 24/7. OWLv2 has graded tutorials, visual exercises, and homework questions. You'll get instant answer-specific feedback to help you every step of the way as you master tough chemistry concepts and skills. OWLv2 allows you to learn at your own pace to ensure you've mastered each concept before you move on. OWLv2 includes an iPad-compatible digital textbook available online 24/7, enhanced with apps and embedded video, and activities for a seamless learning experience. To learn more, 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 with Student Solutions Manual, 4 terms (24 months) Instant Access  (ISBN-10: 130508800X | ISBN-13: 9781305088009)

The eBook for the Student Solutions Manual. This Study Guide and Solutions Manual provide answers and explanations to all in-text and end-of-chapter exercises and include supplemental information to help enrich your chemistry experience.

List Price = $52.00  | CengageBrain Price = $52.00  | College Bookstore Wholesale Price = $52.00

OWLv2 6-Months LabSkills PreLabs for Organic Chemistry Instant Access  (ISBN-10: 1285431723 | ISBN-13: 9781285431727)

Are you ready for your Lab course? Get a better grade in your lab course by working prelab assignments in OWLv2, the #1 online homework and tutorial system for chemistry, available for purchase at www.CENGAGEbrain.com. LabSkills includes step-by-step videos to introduce you to lab techniques, equipment and safety skills needed to successfully complete labs; interactive modules to give you an opportunity to interact with lab equipment prior to lab, so you are familiar with equipment setup and ready to go when you get to lab; safety training and information to ensure that you are prepared to safely complete labs; and quizzes to assess your understanding and retention of key concepts, so you can see where they need further study. To learn more, visit www.CENGAGE.com/owl or talk to your instructor.

List Price = $54.00  | CengageBrain Price = $54.00  | College Bookstore Wholesale Price = $54.00

OWLv2 LabSkills PreLabs for Organic Chemistry, 4 terms (24 months) Instant Access  (ISBN-10: 1285431715 | ISBN-13: 9781285431710)

Are you ready for your Lab course? Get a better grade in your lab course by working prelab assignments in OWLv2, the #1 online homework and tutorial system for chemistry, available for purchase at www.CENGAGEbrain.com. LabSkills includes step-by-step videos to introduce you to lab techniques, equipment and safety skills needed to successfully complete labs; interactive modules to give you an opportunity to interact with lab equipment prior to lab, so you are familiar with equipment setup and ready to go when you get to lab; safety training and information to ensure that you are prepared to safely complete labs; and quizzes to assess your understanding and retention of key concepts, so you can see where they need further study. To learn more, visit www.CENGAGE.com/owl or talk to your instructor.

List Price = $61.00  | CengageBrain Price = $61.00  | College Bookstore Wholesale Price = $61.00

LMS Integrated for OWLv2 with MindTap Reader, 4 terms (24 months) Instant Access  (ISBN-10: 130539870X | ISBN-13: 9781305398702)

Your ticket to better chemistry grades OWLv2 is a proven system to help you succeed. Its Mastery Learning approach allows you to practice at your own pace, receive meaningful feedback and use learning resources to help you achieve better grades. Know what’s important OWLv2 concentrates on what’s most important—understanding chemistry concepts—and its technology lets you work the way that’s best for you Discover the relevance of your lessons Interactive simulations, visualizations, and tutorials integrated smoothly into your lessons. The more you learn, the better prepared you are to solve problems and analyze information – which helps you succeed in exams and in the workplace. Master the content Problems that challenge you to think about the concepts, and a platform that lets you practice what you’ve learned. OWLv2 moves you up the levels from memorization to mastery in a supportive learning environment. Student Testimonial: “I dropped the class first semester due to poor performance on quizzes. There was no OWL offered. This semester I currently have an A and I greatly attest this to OWL.” 1st-Year Student General Chemistry I, University of Dayton CTA: Ask your instructor about OWLv2 for this course. Visit us online: www.cengage.com/OWLv2

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

SpartanModel Electronic Modeling Kit  (ISBN-10: 0495017930 | ISBN-13: 9780495017936)

SpartanModel replaces the plastic models used by past generations of organic chemistry students. A set of easy-to-use builders allow for the construction and 3-D manipulation of molecules of any size or complexity. Each copy includes the software on CD ROM, an extensive molecular database, 3-D glasses, and the Tutorial and Users Guide with 50 pages of activities for organic chemistry.

List Price = $117.95  | CengageBrain Price = $117.95  | College Bookstore Wholesale Price = $89.00

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.