Making the Connections: A How-To Guide for Organic Chemistry Lab Techniques


Anne B. Padías and Joshua M. Osbourn | Fourth Edition

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We are excited to share with you the new fourth edition of Making the Connections. If you are familiar with any of the previous versions, you are aware of the approach, connecting students’ existing knowledge to the situation they are stepping into, the organic lab. And even though there have been plenty of changes since our last edition (see New to This Edition), we have remained true to this methodology. Many of our examples are designed to bridge that gap between what students know now and what they are learning. Another theme we have maintained with this edition is our careful and detailed explanations, often pairing them with four-color illustrations on how to safely perform the essentials of basic lab work. While we can’t cover every scenario and lab setup, we start out with safety on the first page and return to it throughout the entire book. We understand that dangers lurk in an organic lab and require vigilance, knowledge, and common sense to avoid them. As we wrote in the previous edition, when you are in a chemistry building, everyone should be attentive to the potential hazards.

If you are new to our book or considering it for your students, thank you for taking the time to review. If you have questions or have ideas for improving the book, please reach out to us at We always welcome the feedback.

I would like to welcome aboard my new co-author Joshua Osbourn from West Virginia University. You can read all about Josh under About the Author. I want to thank him for translating his passion of helping organic lab students succeed into this new edition. A thank you also goes out to Josh’s colleague, Brian Nichols who double and triple checked the changes.

Chapter 1 – First the Basics

Chapter 1 provides the foundation for success in the organic chemistry laboratory. This chapter begins with a discussion of how to work safely in the lab and properly handle chemical reagents. Next is a discussion of how to record your results and keep a proper lab notebook. An introduction to the most common organic chemistry equipment and techniques is then presented. The chapter concludes with a detailed discussion of solvents and their importance in running reactions and in purification techniques.

Chapter 2 – How to Identify Compounds

Chapter 2 provides an overview of the methods used to identify and characterize organic molecules. This chapter begins with fundamental characterization techniques such as melting point determination, optical rotation, and refractive index. Spectroscopic techniques including infrared spectroscopy and nuclear magnetic resonance spectroscopy are then discussed. Methods of sample preparation as well as a guide to structure elucidation is presented. The chapter concludes with a discussion of mass spectrometry and the fundamentals of how to interpret a mass spectrum.

Chapter 3 – Purification Techniques

Chapter 3 discusses the most common purification techniques used in the organic chemistry laboratory. This includes the recrystallization of solids, distillation of liquids, and methods of extraction. Chromatographic techniques such as thin layer chromatography, column chromatography, and gas chromatography are also discussed.

Chapter 4 – Running a Reaction

Chapter 4 provides a short overview of how to set up and run a reaction from start to finish. This chapter effectively summarizes the concepts covered in Chapters 1–3 in order to carry out a successful reaction. The chapter concludes with a discussion of The Twelve Principles of Green Chemistry and how they can be applied in the teaching laboratory.



It had been seven years since we revised this book. While the concepts of organic chemistry have not changed dramatically during that time, a lot has. Below you will see a chapter-by-chapter breakdown of the updates we have made to this edition. In addition to these improvements, we have also added the following:

  • A new four-color design. We carefully integrated full color into this book for the purpose of enhancing the pedagogy.
  • E-version of the book. Students are growing up in a digital learning environment, and to accommodate them, we have e-book options. We can also create custom e-books.
  • All new end-of-chapter questions.
  • Instructor’s Guide. For adopting instructors, we have made available a guide with all the answers to in-chapter questions.
  • Glossary. New to this edition, students can quickly look up unfamiliar terms.


4th Edition Content Updates

Chapter 1 – First the Basics

  • The section on hazardous chemicals has been updated to include the HCS (Hazard Communication Standard) for container labeling along with the inclusion of HCS pictograms for identifying hazards.

  • The sample laboratory notebook has been completely revised and rewritten. The new version contains several callouts to guide students on proper notebook keeping techniques.

  • Useful equations and calculations have been emphasized with color/callouts to make them easier to identify.

  • A dedicated figure of common organic glassware with pictures has been included to provide a quick visual reference to students who are getting started in the organic laboratory.

  • A solvent miscibility chart is now included with a discussion of miscible and immiscible solvent systems. This chart is referred to when discussing mixed solvents in extraction, distillation, and chromatography.

Chapter 2 – How to Identify Compounds

  • Chemical reference information/databases have been updated to remove out-of-print publications and to include modern resources such as SciFinder and Reaxys.

  • The IR section has been updated to include modern ATR-FTIR instruments.

  • The section on IR interpretation has been completely rewritten to provide a comprehensive guide to analyzing an IR spectrum for each of the common functional groups. Several new IR spectra have been included to illustrate the functional group absorptions. The IR spectra are now labeled to include the structure and have the functional groups and corresponding absorptions highlighted on the spectrum for easy analysis.

  • The section on NMR spectrometry has been rewritten for improved organization.

  • The ¹H NMR spectra have all been revised and now include the chemical structure overlaid on the spectrum.

  • A step-by-step analysis of a ¹H NMR spectrum from identifying chemical shifts, integration, and multiplicity to coupling constants is now included. Pedagogically, this is presented in such a way that the student builds a table of chemical shift data that can be included in their lab notebook or lab report.

  • An all-new colorful chemical shift table is now included in the text and on the inside cover of the book.

  • The tables of ¹H NMR coupling constants have been updated to include aromatic proton coupling constants.

  • A small section on calculating the degree of unsaturation from a molecular formula has been added for quick reference.

  • All new ¹H NMR interpretation examples have been included.

  • A new section on recording and reporting NMR data has been included. This section describes how to report NMR data in paragraph form for inclusion in a publication.

  • In the mass spectrometry section, the fragmentation pattern of n-octane has been updated to include a graphical representation of the various cation and radical fragments that appear.

Chapter 3 – Purification Techniques

  • A section containing methods to induce crystallization has been added.

  • An expanded discussion of using mixed solvent systems for crystallization is now included.

  • The section on azeotropic distillation has been revised for clarity.

  • In the section on chromatography, a discussion and chart of functional group polarity are now included. A table of the eluotropic series is also included to help students choose solvents of the appropriate polarity to perform a chromatographic separation.

  • A new section with commonly encountered TLC issues (streaking, bleeding, overloaded plate, etc.) and potential solutions is now included.

Chapter 4 – Running a Reaction

  • Running a Reaction has been reorganized and expanded into seven sections that guide the student from start to finish in running a chemical reaction and analyzing the products.

  • The section on Green Chemistry has been expanded to include the Twelve Principles of Green Chemistry along with examples of how these principles can be utilized in a synthetic laboratory.

End of Chapter Problems

  • New End of Chapter Problems will be included for each chapter with instructor provided solutions.


  • A glossary will be added to the back of the book to allow students to quickly look up unfamiliar terms.

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Anne Padías received her Ph.D. in chemistry from the State University of Ghent in 1975. She did her postdoctoral work at the University of Arizona with Prof. H. K. Hall, Jr., and spent the next 35 years at that institution. For over 20 of those years, she coordinated the labs, leading to the writing of this book. Her favorite thing about chemistry is the connection between what happens in the lab with what happens in real life: there’s always a real-life application for chemistry.

Josh Osbourn received his Ph.D. in chemistry from the University of Pittsburgh in 2012. He joined the Department of Chemistry at West Virginia University that same year as a member of the teaching faculty. His primary focus is teaching undergraduate and graduate organic chemistry courses and coordinating the organic chemistry laboratories. In 2018, Josh received the WVU Foundation Outstanding Teaching Award for his teaching contributions at the university.