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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.

Increasing access to undergraduate research is critical in efforts to retain students pursuing careers in STEM. Alternatives to traditional research positions, such as course based undergraduate research experiences (CUREs), have played important roles in engaging more undergraduates in research. However, these opportunities are only a subset of possible nontraditional research experiences which can enrich the undergraduate experience. In this study, we critically examined and improved the research-group-led undergraduate research program (GURP) to better meet the needs of undergraduates seeking research. Specifically, we investigated if the program was successful with a greater diversity of data sets, if assessments of learning were consistent across different data sets and teaching environments, and if the program promoted student engagement in research. We have found that this model is scalable, robust, and adaptable to different implementations while producing consistent and positive learning outcomes for students. Especially remarkable are students' increased self-identification as scientists and statistically significant gains in self-perceived competency across multiple domains of knowledge. This program model has shown promising results as a partially and fully online research experience for undergraduates and has benefited program alumni in their research careers. To assist research groups starting similar programs, we have created public data sets and instructional resources. We believe that GURP programs can work in a variety of situations and hope that they can become a tool to increase interest and build communities for young researchers.

Many cultural and institutional barriers have prevented chemistry from realizing greater calls for diversity in academia. Though recent work has elucidated how the measures of success used in academia can disadvantage students from underrepresented groups at the undergraduate level, thorough understanding of how success metrics are valued by minoritized students at the graduate level is lacking. Here, we use data generated from the UC Berkeley Department of Chemistry's student-led climate survey to investigate both how graduate students prioritize and how faculty employ common metrics for graduate student success. Results revealed that faculty undervalued metrics preferred by students from underrepresented groups (URGs) in STEM such as underrepresented people of color, women, LGBTQ+ students, and first-generation students. Priorities of students that do not identify as underrepresented displayed no statistically significant differences compared to faculty values. Questions regarding publication record, one of the often-used measures of success in STEM academia, suggest that graduate students, particularly those belonging to URGs, challenge the use of publication record as the primary metric of success in graduate school. These findings highlight some of the ways that definitions of academic success can be exclusionary for graduate students from underrepresented backgrounds and encourage re-envisioning graduate school success in ways that reflect the values of diverse student populations.

Peer learning programs have been developed to support many introductory science courses by providing additional instruction and engagement. These programs are beneficial to both learners and instructors, providing content learning and confidence and attitudinal gains. There is evidence that the benefits of peer learning are higher when students are taught by a near-peer instructor who is close to the learner in age and experience. Building on this existing evidence, a peer learning program, the Undergraduate Teacher-Scholar (UGTS) Program, was created, involving both graduate student and near-peer instructors teaching in the same discussion or laboratory section. This format creates a vertical learning community within the course structure. The Teacher-Scholar program provides the opportunity to compare the roles of graduate student and near-peer instructors teaching the same students the same instructional material. We report differences and similarities in the perceived roles of the graduate student and near-peer instructors by all of the stakeholders involved in the program. Both graduate student and near-peer instructors are valued by students; however, the near-peer instructors provide mentorship and role model qualities that are not replaced by a graduate student instructor.

Over the past several decades, green chemistry has gained prominence in chemistry education. However, the development of green chemistry curricula has not reached all levels of education equally, focusing mainly on elective and upper division courses. We deliberately focused our green chemistry curriculum redesign on a high enrollment introductory general chemistry laboratory course at the University of California, Berkeley. We developed over 30 new experiments that introduced students to green chemistry concepts and applications, while maintaining canonical general chemistry learning goals. The context of the curriculum and required course assignments encouraged students to use green chemistry principles to explore and solve real-world problems. After completing this redesigned course, we hypothesized that students would value green chemistry and feel more confident in their green chemistry knowledge. We developed new methods to measure students' attitudes toward and understanding of green chemistry as a system instead of isolated reactions or processes. These assessments allowed us to better understand both the progression and limitations in student green chemistry and systems-thinking. Since over 2000 students complete the laboratory course each year, we used a combination of fixed response items and free response items from online surveys and in-class assignments and exams. This approach allowed efficient assessment of thousands of students, while still gaining valuable and nuanced views of student understanding and attitudes. These assessments indicated that the new general chemistry laboratory curriculum succeeded in providing an environment in which students learned green chemistry concepts and realized that chemistry has connections to their future courses and professions.

Participating in undergraduate research yields positive outcomes for undergraduate students, and universities are seeking ways to engage more students in undergraduate research earlier in their academic careers. Typically, undergraduate students perform research either as part of an apprenticeship where a student receives individual mentorship in a research lab setting from an experienced researcher in the field of interest or in a course-based undergraduate research experience where students work in a classroom or teaching laboratory to investigate open-ended research questions. In this work, we implement a model of undergraduate research that combines aspects of those two methods to provide benefits to undergraduate students and research groups. A cohort of 20 first-year undergraduate students at the University of California--Berkeley were recruited to work on a project investigating data previously collected by the Alivisatos research group. Over a semester, these students learned about nanomaterials and the research process, pursued curiosity-driven research in teams, and presented their results at a formal poster session. Students from this program showed quantifiable gains in their self-identification as researchers and scientists. This program was developed to be a model for other research groups, departments, and universities to combine the benefits of traditional apprenticeship research and course-based undergraduate research to provide a research experience for large numbers of undergraduate students early in their college education.