Have you received your copy of Greg Friestad’s Techniques and Experiments in Organic Chemistry: Biological Perspectives and Sustainability? This new lab text motivates students with biological context and gets them thinking about sustainability, while reducing disposal costs to the department.
Here’s an excerpt from Greg’s preface discussing how the project came together at the University of Iowa, and how you can put the new book to use in your organic lab.
Dear Instructor,
My mission in creating this textbook was to develop a green organic chemistry laboratory curriculum that inspires student engagement by emphasizing the connections among chemistry, biology, and sustainability. Incorporating concepts of green chemistry was a key aspect, not only to limit environmental impact and operational costs, but also to appeal to broader student and instructor interests. An important secondary consideration was to integrate the green chemistry with instruction in traditional techniques and glassware for the benefit of those students who need a practical foundation for careers in chemistry or other scientific disciplines and/or graduate study. Thirdly, the textbook needed to be flexible for use in one- or two-semester formats, whether the lab is integrated with the lecture or as a separate course.
How did this project start? At Iowa, we have a one-semester Organic Laboratory course for non-majors that meets twice a week plus lecture, with an enrollment of 150–200 per semester, including some chem majors who take it for scheduling reasons. Our non-majors course was taught without any major curriculum revision for many years. Over this time, many informal discussions about the need for revising some experiments, mainly for reasons of modernization and safety, prompted me to take action. Our graduate student teaching assistants and departmental lab staff recognized the need as well, and were willing and eager to test new experiments, so I began a significant curriculum revision, replacing a couple of experiments per semester. After a few semesters it became apparent that an emphasis on biological perspectives and sustainability had emerged as a coherent theme, and that it was an effective way to reach students with wide-ranging interests. It was then I realized that this emphasis, new for our course, could likely be of interest to the larger Chemistry Education community as well.
Why is a new book needed? Over the years, existing textbooks have tackled waste disposal, safety, and cost issues by downsizing the scale of reactions using specialized glassware that students won’t likely see anywhere else. However, this approach is unsuitable for students who will need familiarity with standard glassware and realistic preparative scale reactions, whether it’s in future employment or in graduate study. The microscale approach deals with the local classroom sustainability problem, but is less effective in teaching students to think about sustainability in real-world chemical processes where large scales are inevitable.
Compared with traditional lab texts—many of which contain hundreds of pages that are often not used in the typical undergraduate setting—a single text combining green chemistry principles and experiments with traditional organic techniques instruction offers cost and convenience advantages to both students and instructors. There is a clear need for this new textbook.
Goals
My motivations for this textbook likely mirror concerns that inspire curriculum revisions at other institutions. I wanted to
- replace certain time-worn experiments that had grown somewhat stale,
- enhance connections to biological chemistry,
- devote increased attention to issues of sustainability, and
- better coordinate topics between lecture and lab.
To address these issues, I began work on the following goals:
ENLIVEN EARLY SEMESTER INSTRUCTION ON TECHNIQUES Teach techniques like melting point, recrystallization, and distillation as means to an end rather than ends in themselves, by placing them in the context of natural product isolation and synthetic reactions. Early semester work in the organic lab would provide students with opportunities to practice techniques in real-world context.
DRAW CONNECTIONS TO BIOLOGICAL CHEMISTRY
Use biology as a cross-disciplinary theme to enhance the appeal to organic lab course populations that often include a large proportion of biology, pre-med, pre-dental, and environmental science students. Examples include:
- Natural product isolation—gas chromatography measurement of the content of terpenes extracted from citrus peels (Chapter 10)
- Grignard reaction followed by a greener oxidation method—preparation of naturally occurring insect pheromones (Chapter 21)
- Plant material as a feedstock for an organic reaction—furfural from corn cobs (Chapter 22)
- Biomimetic thiamine-catalyzed furoin synthesis—a more reliable analog of the classic biocatalytic benzoin condensation (also Chapter 22)
- Enzyme-catalyzed organic reactions—perform biocatalytic reduction with natural enzymes from plant material (Chapter 23)
EMPHASIZE SUSTAINABILITY
Introduce green chemistry early, and emphasize sustainability in a greater proportion of the experiments, while still teaching fundamentals of practical organic chemistry. Students are more motivated when their study of organic chemistry is tied to real-life applications. Going forward in their careers, they will benefit from a foundation that emphasizes the responsibility and accountability of chemists in solving or preventing chemistry-related problems. In addition to introducing the 12 Principles of Green Chemistry in Chapter 1, the text’s experiments:
- Use less hazardous reagents, e.g., green oxidation with hydrogen peroxide (Chapter 16)
- Use renewable resources, e.g., furfural from corn cobs (Chapter 22), light energy for promoting a cycloaddition (Chapter 18)
- Use solvent-free or aqueous reaction conditions, e.g., solventless aldol reaction (Chapter 24)
- Use catalytic transformations that generate less waste, e.g., enzyme-catalyzed reduction (Chapter 23), palladium-catalyzed coupling (Chapter 25)
ALIGN TOPICS WITH COVERAGE IN LECTURE COURSES
Use mechanisms and reactions typically covered in Organic I in the earlier experiments, moving mechanisms and reactions covered in Organic II to later in the book. Instructors of labs that are tied to the lecture course will find this organization useful.
Students who take the lab course later as a one-semester course (as we do here at Iowa) will also learn more effectively by reviewing and reinforcing topics in an organization that parallels lecture courses, building complexity in a logical way.
PROVIDE EXPERIENCE WITH MULTISTEP SYNTHESIS
Several experiments use the product from a previous step as the starting material. In this way, students gain a very personal perspective on reaction efficiency and why it is important. This is valuable for students who will go on in chemistry, of course, but it also benefits students moving on to health sciences careers, so that they can understand how pharmaceuticals are made and why they are so expensive.
CONCLUDING REMARKS
During our development toward the goals outlined above, student engagement improved as judged by comments in student evaluations, and my own interest in teaching the course strengthened. What a great synergy!
Our non-majors’ organic laboratory course at Iowa, with strong themes of biological chemistry and sustainability woven throughout, has proved very appealing to many hundreds of students who have already used the curriculum in this textbook. Their unsolicited positive comments and sincere engagement in the course have been very gratifying, and inspired my proposal to take the text to a wider audience. Quite a lot of critical thinking and adaptations based on instructor, student, teaching assistant, and reviewer feedback have been implemented to make this material more generalizable to other universities and colleges.
I thank you for taking the time to consider this textbook for your course, and
I welcome your feedback so that I can continue to improve it in the years to come.
Greg’s book is available in two paperback formats: techniques and experiments together, and techniques standalone. To request a copy, contact your local Norton representative.
