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Organic Chemistry

Dedication and Preface

Organic ChemistryDedication and Preface

This 10th edition of Organic Chemistry is dedicated to the memory of my son, Peter McMurry, who passed away in 2019 after a lifelong struggle with Cystic Fibrosis (CF). He was brilliant, strong, and truly the kindest person I have ever known.

A photograph of a smiling adult man.
Peter McMurry
12/10/1968 – 12/12/2019

Just about every first-year medical student at New York Presbyterian Hospital/Columbia Medical Center knew and admired Peter, who was asked every year to meet and speak with incoming students about his experiences as a patient. He always enjoyed talking to the students, kidding them about their having had to take organic chemistry in college, and asking them if anyone recognized his last name from their O-Chem textbook.

If Peter were still alive, I have no doubt that he would want me to work on this 10th edition with a publisher that would give the book away free to students rather than with one that would charge a large amount. So that is what I have done. To make this possible, I am not receiving any payment for this book, and generous supporters have not only covered the production costs but have also made a donation to the Cystic Fibrosis Foundation to help find a cure for this terrible disease. Anything that readers of this book might donate in Peter’s memory to the Cystic Fibrosis Foundation would also be much appreciated.

John McMurry

Welcome to Organic Chemistry: A Tenth Edition, an OpenStax resource. This textbook was written to increase student access to high-quality learning materials, maintaining highest standards of academic rigor at little to no cost.

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From the author—About Organic Chemistry: A Tenth Edition

Organic Chemistry: A Tenth Edition, like previous editions, is intended for a two-semester introductory organic chemistry course. I recognize that many students in this course are biology or pre-med majors so, when appropriate, I bring in biological examples. Color is used consistently through the texts and illustrations. Problems are categorized (see below) and vary in level. My goal is to be as economical as possible with changes so that the overall length of Organic Chemistry does not increase.

Changes to the tenth edition

I continue to review every word and every explanation, updating many small details and improving problems where needed. My aim is always to refine the features that made earlier editions so successful, while adding new ones. Reviewer comments are also extensively considered during the reviewer process. All the problems in every chapter are also reviewed for clarity. The detailed list of changes will be available upon publication at the OpenStax website. However, the following is a list of the major changes made to the tenth edition.

Chapter 6

  • Polar Reactions are now covered before Radical Reactions

Chapter 17

  • Section 17.5: Added newly discovered reaction of Grignard reagents with carboxylic acids to prepare ketones

Chapter 18

  • Section 18.7: Added coverage of ionophores

Chapter 19

  • Section 19.5: Added coverage of alpha-keto acid hydrates

Chapter 21

  • Section 21.3: Added synthesis of amides by reaction of carboxylic acids and amines using (1-Ethyl-3-(3-dimethylaminopropylcarbodiimide (EDEC)

Chapter 26

  • Section 26.7: Added synthesis of amides by reaction of carboxylic acids and amines using (1-Ethyl-3-(3-dimethylaminopropylcarbodiimide (EDEC)
  • Section 26.8: Updated details for solid phase peptide synthesis

Chapter 30

  • Section 30.8: Increased coverage of Cope rearrangement
  • Section 30.8: New coverage of Oxy Cope reaction

Chapter 31

  • Section 31.6: Discuss intramolecular olefin metathesis use in ring-closing
  • Chemistry Matters: Discuss intramolecular olefin metathesis use in ring-closing

Coverage and scope

Organic Chemistry: A Tenth Edition, like previous editions, is intended for a two-semester introductory organic chemistry course. The tenth edition retains the functional group approach of prior editions and the table of contents is retained.

Pedagogical foundation and features

  • “Why This Chapter?” is a brief section that appears before the introduction to every chapter and tells students why the material about to be covered is important.
  • Worked Examples includes a strategy and a detailed solution and is followed by problems for students to try on their own. The tenth edition has more than 1800 in-text and end-of-chapter problems.
  • Visualizing Chemistry Problems occur at the end of each chapter. The problems offer students an opportunity to see chemistry in a different way by visualizing molecules rather than by simply interpreting structural formulas.
  • Mechanism Problems are grouped together at the end of each chapter.
  • Summaries and Key Terms lists help students by outlining the key concepts of each chapter.
  • Summaries of Reactions at the ends of appropriate chapters bring together the key reactions from the chapter in one complete list.

Comprehensive art program

The art program is designed to enhance students’ understanding of concepts through clear, effective illustrations, diagrams, and photographs.

About the author

John E. McMurry

John E. McMurry is a Professor Emeritus in the Department of Chemistry and Chemical Biology at Cornell University. He holds an A.B. degree from Harvard University and a Ph.D. from Columbia University. McMurry has authored over 100 research papers and is well-known for his contributions to the field of chemistry, particularly the development of the McMurry reaction. This reaction involves the coupling of two molecules of ketone or aldehyde to produce an alkene when treated with titanium(III) chloride and a reducing agent like Zn(Cu). The McMurry reaction has found extensive use in the laboratory synthesis of complex organic molecules and in the commercial synthesis of various drugs by the pharmaceutical industry.

McMurry was elected a Fellow of the American Association for the Advancement of Science in 1985 and received a Max Planck Society Research Award in 1991. Apart from his scientific contributions, McMurry is also a prolific author in the field of chemistry education. He has written 45 undergraduate chemistry textbooks, which have been translated into 12 languages and used worldwide. Among his notable works, Organic Chemistry, first published in 1984, stands as his most popular textbook.


Mohammed Abrar Alam, Arkansas State University
Pamela Auburn, Lone Star College
Han Baocheng, University of Wisconsin-Whitewater
David Bergbreiter, Texas A&M University
Alfredo Castro, Felician University
Alice Cherestes, McGill University
Daniel Collins, Texas A&M University
Evon Ford, Community College of Baltimore County
Kevin Francis, Texas A&M University-Kingsville
Micheal Fultz, West Virginia State University
Mariusz Gajewski, Arkansas Tech University
Bryant Gilbert, Zane State College
Stewart Hart, University of the Ozarks
Alaa Hashim, University of South Florida
Kjir Hendrickson, Arizona State University
Paul Hudrlik, Howard University
Ekaterina Kadnikova, Hamline University
Bee Kelley, University of Arkansas at Pine Bluff
Nicholas Leadbeater, University of Connecticut
Thomas Lectka, Johns Hopkins University
Saundra McGuire, Louisiana State Univeristy
Evy McUmber, Southwestern College
Ellen Moore, University of Missouri
Jennifer Muzyka, Centre College
Jacqueline Nikles, University of Alabama at Birmingham
Allyn Ontko, Arkansas State University
Justin P'Pool, Franklin College
Phuong-Truc Pham, Penn State Scranton
Vijayakumar Ramalingam, SUNY Polytechnic Institute
Jia Sheng, University at Albany, State University of New York
Ike Shibley, Penn State Berks
Jason Tien, GPCR Therapeutics, Inc.
Coran Watanabe, Texas A&M University
Zhou Zhou, Queensborough Community College

Additional resources

Diversity and Inclusion Modules

Developed independently of this textbook by Dr. Rhett Smith (Clemson University), this resource is a unique website linked to Organic Chemistry: A Tenth Edition. This resource is free for instructors and students to use if they so choose. The website is mapped to Organic Chemistry: A Tenth Edition to provide a more complete, diverse, and inclusive picture of the development and current state of organic chemistry research. The figures whose work is highlighted in this online resource include historical figures from the developmental years of chemistry as well as researchers still active in the community. Each lesson currently consists of a brief introduction followed by a one-page description of the highlighted researcher and their work as it relates to relevant course topics. This is then followed by links to additional readings or videos about the life and research of the highlighted individual as well as quiz questions. The site also integrates into your learning management system (LMS).

Study Guide and Student Solutions Manual

Authored by Susan McMurry, the Student Study Guide and Student Solutions Manual are now separate items. Both the Study Guide and Student Solutions Manual, for the first time, will also be openly licensed and free for students in digital formats. Both resources have been updated to reflect the changes in the text and revised to meet accessibility standards.

Additional resources can be found by going to the instructors resource page for this text.

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Academic integrity builds trust, understanding, equity, and genuine learning. While students may encounter significant challenges in their courses and their lives, doing their own work and maintaining a high degree of authenticity will result in meaningful outcomes that will extend far beyond their college career. Faculty, administrators, resource providers, and students should work together to maintain a fair and positive experience.

We realize that students benefit when academic integrity ground rules are established early in the course. To that end, OpenStax has created an interactive to aid with academic integrity discussions in your course.

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attribution: Copyright Rice University, OpenStax, under CC BY 4.0 license

Visit our academic integrity slider. Click and drag icons along the continuum to align these practices with your institution and course policies. You may then include the graphic on your syllabus, present it in your first course meeting, or create a handout for students.

At OpenStax we are also developing resources supporting authentic learning experiences and assessment. Please visit this book’s page for updates. For an in-depth review of academic integrity strategies, we highly recommend visiting the International Center of Academic Integrity (ICAI) website at

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