Who’s on your team? Undergraduate research in organic chemistry

In this post, Dr. Dave Anderson shares his insights on building teams of undergraduate students to do research in synthetic organic chemistry, publish research papers and shape collaborative, critical thinkers that are ready to take the next step.

Undergraduate research is an inquiry or investigation conducted by an undergraduate with a faculty mentor that makes an original intellectual or creative contribution to the discipline(s).

Wenzel, T. J., “What is Undergraduate Research?” Council on Undergraduate Research Quarterly, 1997, 17, 163

Research with undergraduates is real research, with real outcomes

Some may argue that undergraduate research does not have to result in a published work. Perhaps, a student project should be reported instead in an “undergraduate journal”, in which case a student project might stand alone, but not be of sufficient impact to warrant publication in a research journal. Our view of this has evolved over time, but we maintain that research with undergraduates is real research worth reporting, and publications in research journals serve are the best evidence of a student’s motivation to move into graduate research at a highly competitive research institution. Publications that accumulate data from a team of undergraduate student researchers over several years are the norm in PUI synthetic organic chemistry labs, and we’ll argue that the effort is worth it. But publications aren’t the only outcome.

Research in synthetic-organic chemistry (my area) is full of experiments that fail, particularly those that are “exploratory”. When a reaction does not go as planned, students learn about the ups and downs of research, but they also learn to persist in the face of adversity. If a literature prep fails, that is an opportunity for critical self-reflection. When an exploratory reaction does not go as planned, there is an opportunity for creative-thinking and innovation. Did the reaction produce an unanticipated product? If no product was formed, were the starting materials recovered? Sometimes failures or unexpected outcomes can lead to new beginnings, even separate research projects!

We have found that many students who want to participate in undergraduate research join right in and become enthusiastic and productive research workers. There are always some who change direction and their experience helps them discern a new path – away from research, try a different type of research or even pursue a different major. We view that as a healthy outcome for them, if not for our personal research program. Organic chemistry research isn’t for everyone, but just participating in the process – for however long – teaches students something about themselves.

Recruiting and on-boarding student researchers in the organic synthesis lab

Recruiting students for the synthetic organic research lab starts early! An effective strategy is to make cameo appearances in general chemistry courses so that younger students are aware that research opportunities are available for them. When we do appearances, we bring research students along and make the point that these students were sitting right there in general chemistry only a year or two ago. This can be an effective way to present research opportunities to students, since many will not approach a faculty member in his or her office to ask for a research experience.

A rigorous instructional organic laboratory experience is desirable for students want to pursue productive research. If a student needs extensive skills training, then it is additional time and effort on our part to get that student up to speed. Instead, we try to use the two-labs per week laboratory program accompanying the one-year organic course sequence as our training ground. This course-based instructional lab places an emphasis on basic skills, preparation separation and purification of compounds, synthetic sequences and characterization by spectroscopic and other methods.

After the typical sophomore-year organic laboratory experience, students are ready to transition from instructional to research lab. By the spring of the sophomore year, they can learn the different organization of the research lab, proper storage of chemicals, commercial sources of reagents, safe handling of chemicals and the placement of the various categories of chemical wastes in the proper containers. For example, a heavy emphasis is placed on laboratory safety, accident prevention and what to do in case of an accident. All research students wear googles and lab coats, and gloves are worn when handling chemicals. Finally, students learn to search the literature, design experiments and keep a research notebook.

During that sophomore spring, training of new students in the organic synthesis research lab also includes following literature preparations and experiments done by previous students. Following established methods at first allows students to get into the routine of working in the research laboratory, while also building confidence as they master each process. Working alongside other, more experienced, students builds confidence and camaraderie. For example, new student researchers (often sophomores) often observe more senior students doing their chromatographic separations. As students become more experienced in the research lab, they learn additional techniques such as plumbing the LC instrument and clipping the capillary columns to get better-looking chromatograms. They may learn advanced NMR techniques, such as obtaining and interpreting HSQC and HMBC spectra.

By the end of the spring term, freshly trained sophomores are assigned projects, so they can hit the ground running during the summer term, when they have more time for research. When assigned a project, a student will most often have to plan several synthetic steps and use larger quantities of reagents for the earlier steps – all in careful consultation with the faculty-mentor. When a student researcher finally prepares their first “new compound”, the purification and characterization are nothing short of exhilarating! The student collects spectra and other analytical results, sharing in their investigation and ultimate success with the faculty-mentor and fellow students.

At the bench and beyond: results are a team effort

Each step of the training process requires teamwork, and each publication is the product of teamwork. Nearly two years of effort is necessary for an undergraduate organic synthesis researcher to be able to contribute significantly to a research publication. And we have found, that it’s necessary for students to work at least half-time during the summer in order make significant contributions to the team. In the end, it is very likely that a paper will be co-authored by several undergraduates who have carved out time from their busy schedules to squeeze in some research time during the academic year.

Uninterrupted summer research time is so important for students to make significant progress and contributions to the team. Therefore, access to summer funding is critical. Internal funding has been the most important method of support for our undergraduates. Many students on our campus need part-time work, and working in the lab for remuneration can make it possible for them to be part of our research team. Other students prefer to work for academic credit. We generally provide for one or the other.

While a graduate lab is an assembly of researchers working under a common PI, graduate students are more likely to be concerned with their own efforts to achieve a successful thesis, the result of a largely individual effort. In contrast, we have found the undergraduate experience to be more collegial and collaborative, with students supporting and encouraging one another. Undergraduate research students love group camaraderie, informal social events and more formal events, such as group meetings and end-of-term group lunches, and it is this team that develops the student at the bench and beyond.

Planning student research projects requires purpose, belonging and an an opportunity to share.

Projects are more appealing to undergraduates if they have some reasonable rationale or purpose. For example, a synthetic polymer target might be characterized by a collaborator or tested for biological activity in a collaborator’s lab. The results of these collaborations are then shared with all. In some cases, students can share in the testing process.

Individual student projects are usually presented in terms of what an entire project looks like. For example, a student may receive the rationale for a grant or a partially completed paper so that the student can get an idea of where his or her part of the work fits into the overall scheme. If a project is closer to the beginning where not much as been done, there is an opportunity for more “exploratory” work. Perhaps we can predict, but don’t know for sure what product to expect for a reaction.

Summer research students are typically the most productive, so presentation of their projects is a natural and rewarding conclusion to the summer semester. Each student prepares a presentation given to members of our group and guests near end of the summer term. Students then present on the final day of the term as part of a conference of researchers from all chemistry and biochemistry summer research groups.

A group of people posing for a photo

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A group photo from the 2019 summer research conference

Students from our group are required to submit a report using a journal format with Supporting Information by the end of the week following the presentations. By the time the report is written each student will have searched for and read several key references in order to better understand the rationale for the project. Students may also have the opportunity to present their results at local and regional conferences and particularly at national ACS meeting thanks to generous support from the Colorado ACS section for student travel stipends!

Conclusion – the impact is worth it

Those two years with your students researchers go quickly. Before you know it, your research students are looking to apply to graduate programs during the fall of their senior year. Barely two years ago, those brand-new sophomores were running a flash-prep column for the first time, and now they are speaking with other research group members and their mentors as a co-researcher and colleague. Helping to match a senior student with a graduate program and advisor in their area of their interest is a rewarding conclusion to their undergraduate research career, and a moment where the fruits of team-building are evident. Discussions of possible graduate programs and career choices take place within the same faculty-mentor and student team that nurtured individual from the beginning. At no point is it more obvious that research with undergraduates is a high-impact practice and a privilege.

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