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Problem solving is a key component of authentic scientific research and practice in organic chemistry. One factor that has been shown to have a major role in successful problem solving in a variety of disciplines is metacognitive regulation, defined as the control of one's thought processes through the use of planning, monitoring, and evaluation strategies. Despite the growing interest in assessing and promoting metacognition in the field of chemical education, few studies have investigated this topic in the context of organic chemistry students. To gain a deeper understanding of how and why students make use of strategies related to metacognitive regulation in their approaches to solving problems, we conducted interviews with Organic Chemistry I, Organic Chemistry II, and graduate organic chemistry students and used multiple measures to examine students' metacognition. As a part of these interviews, students verbalized their thoughts as they worked on complex predict-the-product problems and completed a self-report instrument indicating which planning, monitoring, and evaluation strategies they had used while completing each problem. Think-aloud protocols were analyzed for the presence of each of the behaviors included on the self-report instrument, and students' use of metacognitive strategies was compared to identify differences between students with different levels of experience and between students who generated more and less successful solutions to the problems. Students who generated more successful solutions to the problems tended to report using a greater number of metacognitive strategies. When asked why they did or did not use certain metacognitive strategies, students indicated a number of factors, such as not feeling able to use these strategies effectively or believing that using these strategies was unnecessary. The results of this study support the importance of teaching metacognitive problem-solving strategies in organic chemistry courses and suggest several methods for the assessment and instruction of metacognition.

A central practice in the discipline of organic chemistry is the ability to solve certain fundamental problems, including predicting reactivity, proposing mechanisms, and designing syntheses. These problems are encountered frequently by both students and practitioners, who need to utilize vast amounts of content knowledge in specific ways to generate reasonable solutions. To gain insight into how one of these major problem types can be solved, we have investigated student approaches to complex predict-the-product problems through the detailed analysis of think-aloud interviews. This work led to the creation of a general workflow model that describes the reasoning pathways of students with varying levels of expertise when attempting to predict organic reactivity. The problems used in this study were designed to be non-trivial and potentially ambiguous to elicit ''true'' problem solving and discourage a purely memorization-based approach, even from more experienced organic chemists. Rich descriptions of undergraduate and graduate student interviews are provided, and student thought processes are characterized in terms of common problem-solving actions. These actions were developed into the workflow model using an iterative method that combined results from our analysis with the experiences of instructors and feedback from both undergraduate focus groups and graduate students. The workflow serves as both a potential instructional tool and a model for student thinking. This model is general enough to be applied to both successful and unsuccessful solution pathways by both novice undergraduates and more expert-like graduate students. Characteristics of more successful and more experienced problem solvers are investigated, and concrete strategies that can be recommended to students are discussed. The results of this study complement existing work on other fundamental problem types in organic chemistry and suggest a variety of teaching interventions to develop students into more successful organic problem solvers.

Understanding 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. We report on the Berkeley Undergraduate Research Evaluation Tools (BURET), designed to assess the learning outcomes of UREs and CUREs in chemistry and other sciences. To validate the tools, we administered BURET to 70 undergraduate students in the College of Chemistry and 19 students from other STEM fields, comparing the performance of students who had less than one year of undergraduate research to those with more than one year of research experience. Students wrote reflections and responded to interviews during poster presentations of their research project. BURET asks students to communicate the significance of their project, analyze their experimental design, interpret their data, and propose future research. Scoring rubrics reward students for integrating disciplinary evidence into their narratives. We found that the instruments yielded reliable scores, and the results clarified the impacts of undergraduate research, specifically characterizing the strengths and weaknesses of undergraduate researchers in chemistry at our 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. First-year 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 areas for faculty members, graduate student research mentors, and CURE or URE programs to improve undergraduate research experiences.