Conditions of Use
Yes. This textbook covers a wealth of organic chemistry content and could be used for three organic chemistry courses--Organic Chemistry I, Organic Chemistry II, and Advanced Organic Chemistry. Key terms can be found bolded in the text, and in a... read more
Yes. This textbook covers a wealth of organic chemistry content and could be used for three organic chemistry courses--Organic Chemistry I, Organic Chemistry II, and Advanced Organic Chemistry. Key terms can be found bolded in the text, and in a list at the end of each chapter with links to where they are used in the text. The Study Guide and Student Solutions manual are also openly licensed and free for students in digital formats.
The content appears to be essentially error-free. There may be a missing chemical subscript missing in a place, or two, but nothing that will confuse a student or hinder their learning.
The content is current with applications to everyday life at the end of each chapter in a section titled, “Chemistry Matters.” Examples range from the importance of Vitamin D, to how epoxy resins and adhesives are used in commercial products, to cocaine and anesthetics.
The text is very easy to follow with figures and tables well-placed. New terms are highlighted and strengthen content knowledge.
Yes, each chapter is displayed in the same format beginning with a "Why is this important" and ending with "Chemistry Matters." The subsections are consistent as well.
The textbook has excellent modularity. I see chapters that can be pulled for three different courses—Organic Chemistry I (Chapters 1-13); Organic Chemistry II (Chapters 14-24); and Advanced Organic Chemistry (Sections 5.9-5.12, Chapter 30, and 31), where students can read a later chapter and understand it at a particular level without rereading a previous chapter.
The order of the content is different than the text I normally teach from, but the author does an excellent job of defending this specific order, so I think I’ll give it a try. I like the chapter on “An Overview of Organic Reactions” before diving into reaction classes. I think it will help students recognize the similarities and patterns between reactions. I normally teach the mass spec, NMR and IR chapters out of order, sooner than listed. The analysis of those instruments is so different, that students normally struggle with such a “different” concept at the end of a semester.
One inconsistency that I found distracting was the size of the structures throughout the text. In one table, the chemical structures changed size from molecule to molecule which distracted from the flow. The interface was okay moving between the end-of-section practice problems and the solutions, but it gave away all of the answers with one click. I was also hoping for a bit of interaction with the 3D molecules. I was expecting to be able to manipulate them. While that certainly goes beyond what a typical textbook can do, that would certainly make the online textbook far more engaging.
I did not notice any.
I was pleased to see a linked resource by Dr. Rhett Smith (Clemson University) to provide a “more complete, diverse, and inclusive picture of the development and current state of organic chemistry research.” This component acknowledges the need for diversity. While there was a Japanese track team, a black music conductor (leading a white orchestra), and one sunbather of color, the majority of images were of white people (scientist on the computer (though female), pole vaulter, Kansas City pitcher, officer with a "drunkometer" test, kayaker, rock climber, officers with tear gas masks, etc.). I would have appreciated more diversity in the images.
I do really like the content, the level of explanation, the images, and clarity of this textbook. I plan to use it for my Organic Chemistry II course next spring, as well as my Advanced Organic Chemistry course.
Table of Contents
- Dedication and Preface
- Chapter 1: Structure and Bonding
- Chapter 2: Polar Covalent Bonds; Acids and Bases
- Chapter 3: Organic Compounds: Alkanes and Their Stereochemistry
- Chapter 4: Organic Compounds: Cycloalkanes and Their Stereochemistry
- Chapter 5: Stereochemistry at Tetrahedral Centers
- Chapter 6: An Overview of Organic Reactions
- Chapter 7: Alkenes: Structure and Reactivity
- Chapter 8: Alkenes: Reactions and Synthesis
- Chapter 9: Alkynes: An Introduction to Organic Synthesis
- Chapter 10: Organohalides
- Chapter 11: Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
- Chapter 12: Structure Determination: Mass Spectrometry and Infrared Spectroscopy
- Chapter 13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy
- Chapter 14: Conjugated Compounds and Ultraviolet Spectroscopy
- Chapter 15: Benzene and Aromaticity
- Chapter 16: Chemistry of Benzene: Electrophilic Aromatic Substitution
- Chapter 17: Alcohols and Phenols
- Chapter 18: Ethers and Epoxides; Thiols and Sulfides
- Chapter 19: Aldehydes and Ketones: Nucleophilic Addition Reactions
- Chapter 20: Carboxylic Acids and Nitriles
- Chapter 21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
- Chapter 22: Carbonyl Alpha-Substitution Reactions
- Chapter 23: Carbonyl Condensation Reactions
- Chapter 24: Amines and Heterocycles
- Chapter 25: Biomolecules: Carbohydrates
- Chapter 26: Biomolecules: Amino Acids, Peptides, and Proteins
- Chapter 27: Biomolecules: Lipids
- Chapter 28: Biomolecules: Nucleic Acids
- Chapter 29: The Organic Chemistry of Metabolic Pathways
- Chapter 30: Orbitals and Organic Chemistry: Pericyclic Reactions
- Chapter 31: Synthetic Polymers
- Appendix A. Nomenclature of Polyfunctional Organic Compounds
- Appendix B. Acidity Constants for Some Organic Compounds
- Appendix C. Glossary
- Appendix D. Periodic Table
- Answer Key
About the Book
John McMurry's Organic Chemistry is renowned as the most clearly written book available for organic chemistry. In John McMurry's words, "I wrote this book because I love writing. I get great pleasure and satisfaction from taking a complicated subject, turning it around until I see it clearly from a new angle, and then explaining it in simple words." In Organic Chemistry: A Tenth Edition from OpenStax, McMurry continues this tradition while updating scientific discoveries, highlighting new applications, scrutinizing every piece of art, and providing example problems to assist students. Organic Chemistry: A Tenth Edition continues to meet the scope and sequence of a two-semester organic chemistry course that follows a functional group approach. A highlighted list of changes along with a detailed table of contents and ancillary descriptions can be found on the Instructor and Student resources sections of this page. John McMurry decided to publish Organic Chemistry: A Tenth Edition under an open license as a tribute to his son, Peter McMurry, who passed away from cystic fibrosis in December 2019. Please click here to learn more about Peter's legacy and to support the fight against cystic fibrosis.
About the Contributors
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.