Problem solving in organic chemistry and undergraduate research: Characterizing and catalyzing the transition from novice to expert

I have created a general workflow that describes how students reason through non-trivial organic predict-the-product problems. This was accomplished through an iterative process that combined the experiences of instructors with holistic impressions of think-aloud interviews, incorporating feedback from both undergraduate focus groups and graduate students. The workflow serves as both a potential instructional tool and a model for student thinking. An analysis of think-aloud interview data showed that the workflow describes both undergraduate and graduate student thought processes. Successful and unsuccessful problem solvers did not differ in which problem-solving actions they took. However, the successful problem solvers were more likely to name relevant functional groups, which is a simple and concrete action that can be recommended to students. Graduate student approaches were not qualitatively different than those of undergraduate students, but an increase in focus on deciding between multiple pathways suggests that more expert-like practitioners may frame the problem in a different way. If we want to help students to utilize more high-level reasoning when predicting organic reactivity, they need to be exposed to more situations in which multiple reasonable solutions are possible./nAdditionally, I have developed and implemented two organic chemistry lessons, one on the broad topic of acid-base chemistry, and another on the narrower topic of directing group effects in electrophilic aromatic substitution. These lessons were designed based on the Preparation for Future Learning (PFL) framework, which involves students collectively exploring data to find contrasting cases and “invent” chemical principles. Student performance was measured by pre-tests, immediate post-tests, and scores on relevant exam questions. While the acid-base lesson did not result in an immediate benefit relative to lecture alone, there appeared to be a delayed effect. Students who attended the PFL lesson scored significantly higher on acid-base questions on the final exam, even though this was not the case on the midterms. Assessment on directing group effects suffered from a ceiling effect, making it difficult to draw any conclusions about that lesson. Student feedback on both lessons was overwhelmingly positive. In general, students who attended the lessons felt much more prepared for when the material covered in these lessons was subsequently introduced in lecture. Students also enjoyed the overall format of working with the data to discover trends. Overall, PFL lessons show promise as a useful and active way to familiarize students with various chemical principles prior to their “official” introduction in class./nUnderstanding the impact of undergraduate research experiences (UREs) and course-based undergraduate research experiences (CUREs) is crucial as universities debate the value of allocating scarce resources to these activities. I have designed and tested the BURET instruments, a new set of tools designed to assess the learning outcomes of UREs and CUREs in the sciences. To study the BURET instruments, they were administered to 89 undergraduate students, and the performance of students who had less than one year of undergraduate research was compared to those with more than one year of research experience. Students were assessed on four primary dimensions based on written reflections and poster presentations for their own research project: communicating the significance of their project, analyzing their experimental design, interpreting their data, and proposing future research. The instruments were found to yield reliable scores and helped clarify the impacts of undergraduate research, providing insight into the strengths and weaknesses of undergraduate researchers at this institution. Students with at least a year of research experience were able to use disciplinary evidence more effectively than those with less than one year of experience. Novice students excelled at explaining the societal relevance of their work, but they incorporated only minimal discussion of prior research into their reflections and presentations. Students at all levels struggled to critique their own experimental design. These results have important implications for undergraduate learning, suggesting ways for faculty members, graduate student research mentors, and CURE or URE programs to optimize undergraduate research experiences.

Advisor: Baranger, Anne M