Publications

First-author publications

Feelings of Shame in a First Semester Organic Chemistry Course: Associations between Shame and Examination Performance for Multiple Learner Groups
2024. Stephanie J.H. Frost, Justin M. Pratt, Jeffrey R. Raker. Journal of Chemical Education.
Publisher's Version

Shame is a largely understudied construct in chemistry course contexts compared to other feelings and experiences (e.g., test anxiety, motivation). Introductory organic chemistry courses offer a unique context for exploring shame as the course has a particular reputation for being difficult and many learners begin the course concerned about their performance due to its importance for future studies, both stances associated with an increased potential to experience shame. In this study, we explore shame using the Control-Value Theory lens, considering the relationship between shame and performance measures and any differences between shame experiences and learner groups (i.e., binary sex and race/ethnicity). We measured shame using the Achievement Emotions Questionnaire-Organic Chemistry (AEQ-OCHEM) in the first semester of a yearlong organic chemistry course; shame was measured in relation to the classroom, study, and testing contexts. Confirmatory factor analyses resulted in evidence of appropriate model fit, with necessary measurement invariance evidence for group comparisons. Results corroborate the theory that shame experiences are associated with performance (e.g., increased shame is associated with decreased organic chemistry examination performance). Results of two-way ANOVAs resulted in evidence of differing shame experiences by learner groups (i.e., binary sex and race/ethnicity) despite no evidence of differences by those groups in examination or overall course performance. These results suggest that chemistry instructors should be cognizant of their classroom environments, consider the messaging of high-stakes assessments, and implement activities to assist chemistry learners in coping with shame (and other negative) experiences. Researchers should consider how shame is interrelated with other measures associated with course performance (e.g., motivation, utility value) and how shame experiences across time are reciprocally associated with chemistry course performance.
Motivation Differences in First-Semester Organic Chemistry: A Comparison between First-Time-in-College Students and Transfer Students
2024. Stephanie J.H. Frost, Guizella A. Rocabado, Justin M. Pratt, Jeffrey R. Raker. Journal of Chemical Education.
Publisher's Version

Transfer students are a growing population at four-year higher education institutions, especially in STEM degree programs. Though much work has explored the broad transfer student experience, the experience of these students within specific courses is understudied. Furthermore, knowledge of how transfer students approach STEM courses and their affective experience is lacking. We report, herein, on the motivation differences between first-time-in-college students, Florida community college transfer students, and transfer students from non-Florida community college institutions in the first semester of an introductory organic chemistry course. We use the Academic Motivation Scale-Chemistry, an assessment previously used in multiple general chemistry and organic chemistry course contexts including at our study site, to measure motivation. We found a lack of evidence for a difference between motivation for all admission types, even though there are persistent differences between these groups’ course performances. This finding challenges the assumption that transfer students are less or differently motivated than their peers. A goal of reporting this work is to place emphasis on the importance of faculty members knowing the students enrolled in their courses particularly beyond gender or race/ethnicity demographics, exploring the unique learning experiences of students in their courses, and how faculty members play an important role in the success of students in their courses beyond content learning.
Evaluating electrophile and nucleophile understanding: a large-scale study of learners’ explanations of reaction mechanisms
2023. Stephanie J.H. Frost, Brandon J. Yik, Amber J. Dood, Daniel Cruz-Ramírez de Arellano, Kimberly Bliss-Roche, Jeffrey R. Raker. Chemistry Education Research and Practice.
Publisher's Version

A deep understanding of organic chemistry requires a learner to understand many concepts and have fluency with multiple skills. This understanding is particularly necessary for constructing and using mechanisms to explain chemical reactions. Electrophilicity and nucleophilicity are two fundamental concepts to learning and understanding reaction mechanisms. Prior research suggests that learners focus heavily on explicit structural features (e.g., formal charge) rather than implicit features (e.g., an open p-orbital) when identifying and describing the role of electrophiles and nucleophiles in reaction mechanisms; however, these findings come from small-scale, interview-based investigations with a limited number of reaction mechanisms. The work reported herein seeks to further explore the meaning learners ascribe to electrophiles and nucleophiles by evaluating 19 936 written explanations from constructed-response items asking what is happening in reaction mechanisms and why it happens for 85 unique reaction mechanisms across a yearlong postsecondary organic chemistry course. To analyze these data, we developed an electrophile rubric to capture learners’ level of explanation sophistication (Absent, Descriptive, Foundational, and Complex); this electrophile rubric is complementary to a nucleophile rubric previously reported in the literature. Our data show proportional levels of explanation sophistication for electrophiles and nucleophiles (τb = 0.402) across these written explanations of reaction mechanisms. We note that learners’ explanations of nucleophiles tend to be at a higher level than their explanations of electrophiles. While this finding does support prior literature reports, we also found that explanations of mechanisms involving reductions of pi-bonds (e.g., carbonyls) tended to be more sophisticated for electrophiles than for nucleophiles. Overall, our results support the claim that learners are able to discuss both electrophilicity and nucleophilicity; however, learners discuss electrophilicity and nucleophilicity at different levels of sophistication where nucleophilicity predominates for most reaction types.

Contributed publications

Impact of Prompt Cueing on Level of Explanation Sophistication for Organic Reaction Mechanisms
2024. Caroline J. Crowder, Brandon J. Yik, Stephanie J. H. Frost, Daniel Cruz-Ramírez de Arellano, Jeffrey R. Raker. Journal of Chemical Education.
Publisher's Version

Understanding reaction mechanisms is integral to success in organic chemistry; however, prior research suggests that learners struggle with recognizing the importance of underlying implicit features in reaction mechanisms. Because of this struggle, understanding how learners’ reason about reaction mechanisms and developing assessments to elicit certain types of reasoning has been a topic of great interest in organic chemistry education research. Much of the work with assessments and learner reasoning focuses on scaffolding simple reaction mechanism prompts; however, what has not been focused on is how modifying the levels of prompt support impacts learner reasoning. This work seeks to evaluate the impact of varying cueing in constructed-response assessment prompts on the level of explanation sophistication for nucleophiles and electrophiles. Assessment prompts utilize five reaction mechanisms commonly taught in first-semester organic chemistry. Previously reported nucleophile and electrophile rubrics were used to analyze 2,079 written explanations by learners. Our data for all five reaction mechanisms suggest that our highest cued prompt somewhat elicits higher levels of explanation sophistication. However, when each reaction mechanism is considered individually, we found no differences between the prompt used and level of explanation sophistication for three of the five reaction mechanisms. Our data suggest a more inconclusive overall finding. We emphasize the instructional context, learners’ knowledge limitations during assessment, and the extent to which more cueing and scaffolding in the assessment item is necessary to elicit desired responses. Our results confirm that assessments drive learning, even when considering a null and nuanced finding of our study.
Generalized rubric for level of explanation sophistication for nucleophiles in organic chemistry reaction mechanisms
2022. Brandon J. Yik, Amber J. Dood, Stephanie J. H. Frost, Daniel Cruz-Ramírez de Arellano, Kimberly Bliss-Roche, Jeffrey R. Raker. Chemistry Education Research and Practice.
Publisher's Version

Reaction mechanisms are central to organic chemistry and organic chemistry education. Assessing understanding of reaction mechanisms can be evaluated holistically, wherein the entire mechanism is considered; however, we assert that such an evaluation does not account for how learners variably understand mechanistic components (e.g., nucleophile, electrophile) or steps (e.g., nucleophilic attack, proton transfer). For example, a learner may have proficiency of proton transfer steps without sufficient proficiency of a step where a nucleophile and electrophile interact. Herein, we report the development of a generalized rubric to assess the level of explanation sophistication for nucleophiles in written explanations of organic chemistry reaction mechanisms from postsecondary courses. This rubric operationalizes and applies chemistry education research findings by articulating four hierarchical levels of explanation sophistication: absent, descriptive, foundational, and complex. We provide evidence for the utility of the rubric in an assortment of contexts: (a) stages of an organic chemistry course (i.e., first or second semester), (b) across nucleophile and reaction types, and (c) across prompt variations. We, as well, present a case study detailing how this rubric could be applied in a course to collect assessment data to inform learning and instruction. Our results demonstrate the practical implementation of this rubric to assess understanding of nucleophiles and offer avenues for establishing rubrics for additional mechanistic components, and understanding and evaluating curricula.