Analysis of resources applied to rationalize elimination mechanisms

Gao, Sean; Outlaw, Taylor C.; Liang-Lin, Jason G.; Feng, Alina; Shimomura, Reika; Roizen, Jennifer L.; Cox, Charles T.

doi:10.1039/d3rp00031a

Cited by 3 publications

(3 citation statements)

References 62 publications

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“…41 The research study examines how students solve problems using the resources activated by the question prompt and structure during the problem-solving process. Similar to research reports from Braun and Graulich 43 and Gao, Outlaw et al, 32,44 the research prompts and chemical structures differ, which can result in activation of differing resources. 36,37 The resources framework also emphasizes that experience with a wider range of prompts will impact the specific resources activated.…”

Section: Resources Frameworksupporting

confidence: 68%

“…The research study examines how students solve problems using the resources activated by the question prompt and structure during the problem-solving process. Similar to research reports from Braun and Graulich and Gao, Outlaw et al, , the research prompts and chemical structures differ, which can result in activation of differing resources. , The resources framework also emphasizes that experience with a wider range of prompts will impact the specific resources activated. , Given the focus on both OC1 and OC2, the participants from the two courses will have differing extents of experience in analyzing organic structures. Additionally, similar to research by Kranz et al, we seek to develop themes based on these observations to develop scaffolding activities to promote both activation and productive use of resources.…”

Section: Theoretical Frameworkmentioning

confidence: 75%

“…Students were successful in identifying the geometry but were not successful in analyzing the structure or productively applying resonance. As iterated by previous research, , we need to make sure our summative and formative assessments are functioning as intended. It is particularly paramount to carefully construct and complete an in-depth analysis of multiple-choice items. − …”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Conjugation Amplifies Complexity: A Comparison of Problem-Solving Strategies Across the Organic Chemistry Sequence

Cox,

Shimomura,

Hall

et al. 2024

J. Chem. Educ.

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Resonance structures are central representations in organic chemistry that explain trends in acidity, reactivity, geometry, and stability. Despite being a central representation, prior research findings have shown that students' productive application of resonance as a resource is context-dependent. This research reports findings from a cross-sectional analysis study investigating how Organic Chemistry I (OC1) and Organic Chemistry II (OC2) students use resonance structures to describe acid−base properties, chemical shifts, and geometry. Six students from OC1 and six from OC2 participated in semistructured interviews to capture their problem-solving pathways. Each prompt was designed to be answered using resonance structures. OC1 students, who noted resonance, were less successful with drawing and applying resonance structures than OC2 students, as expected. However, both cohorts used resonance structures to a limited extent, despite the similarities of molecules presented within each prompt. Resources that do not require structural manipulation, such as s-character and electronegativity, were commonly activated instead of resonance across both courses.

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Section: Resources Frameworksupporting

confidence: 68%

Section: Theoretical Frameworkmentioning

confidence: 75%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Conjugation Amplifies Complexity: A Comparison of Problem-Solving Strategies Across the Organic Chemistry Sequence

Cox,

Shimomura,

Hall

et al. 2024

J. Chem. Educ.

Self Cite

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Flipping the script in organic reaction mechanism instruction: using generative pedagogies instead of lecture to improve learning outcomes

Haindfield,

Cerbin,

Baumann

et al. 2024

Chem. Educ. Res. Pract.

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Student conceptualizations and predictions of substitution and elimination reactions: what are they seeing on the page?

Hunter,

Groenenboom,

Farheen

et al. 2025

Chem. Educ. Res. Pract.

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The current study aims to contribute to the literature on how organic chemistry students weigh various factors when predicting products of substitution and elimination reactions. This study focuses specifically on these mechanism types, as they are often the first instances where students must consider the “how” and the “why” of how reactions occur. Previous literature highlights that such reasoning can be challenging. To better support our students, it is essential to understand how they conceptualize these mechanisms. Here, we present results from an investigation into how students compare bimolecular and unimolecular substitution and elimination reactions (SN1, SN2, E1, E2). Students completed tasks involving case comparisons and “predict-the-product” exercises. Through the analysis of nine semi-structured interviews using coordination class theory, we found that (1) students placed a greater emphasis on the importance of the starting substrate in the outcome of a reaction, and (2) focused less on the function of the nucleophile or base in each reaction. Using coordination class theory, we identified visual features and knowledge elements that students coordinated, allowing us to create “resource graphs” that represented students’ conceptualizations. These graphs helped visualize the trajectories of students’ predictions by illustrating how they balanced multiple factors. We discuss implications for supporting students in distinguishing among reaction mechanisms.

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Analysis of resources applied to rationalize elimination mechanisms

Abstract: This study aimed to analyze second-semester organic chemistry students’ problem-solving strategies, specifically focusing on the resources activated while solving problems on E2, E1, and E1cB elimination reactions. Using the theoretical...

Cited by 3 publications

References 62 publications

Conjugation Amplifies Complexity: A Comparison of Problem-Solving Strategies Across the Organic Chemistry Sequence

Conjugation Amplifies Complexity: A Comparison of Problem-Solving Strategies Across the Organic Chemistry Sequence

Flipping the script in organic reaction mechanism instruction: using generative pedagogies instead of lecture to improve learning outcomes

Student conceptualizations and predictions of substitution and elimination reactions: what are they seeing on the page?

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