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Instructional materials in organic chemistry include a wide variety of representations, such as chemical formulas, line-angle diagrams, ball-and-stick diagrams, and electrostatic potential maps (EPMs). Students tend to focus on explicit features of a representation while they are reasoning about chemical concepts. This study examined the affordances of electrostatic potential maps in students’ approaches when the maps were integrated into four foundational organic chemistry problems using an experimental design approach. First-semester organic chemistry students were surveyed from two different institutions, where they made predictions and explained their reasoning behind identifying an electrophilic site, predicting the product, selecting the faster reaction, and classifying a mechanism. Students were randomly assigned to one of four surveys that differed by the representation they were given for the prompts: chemical formula, line-angle diagram, ball-and-stick diagram, and EPM. Responses from students with EPMs were analyzed and compared to responses from students with the non-EPM representations. Results indicated that students with EPMs had higher performance depending on the problem. They were also more likely to cite electronic features such as electron density, nucleophilicity, etc., and were more likely to use causal reasoning in their explanations. This study offers evidence in support of affordances of EPMs in promoting students’ use of electronic features and causal reasoning. This evidence adds to the chemistry education literature by offering a potential means for promoting students’ use of electronic features and causal reasoning by incorporating EPMs into assessment items. Implications for instruction include using EPMs in both instruction and assessment as a tool to help students build skills around invoking electrostatics and causal reasoning to solve problems in organic chemistry.
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Student perceptions of partial charges and nucleophilicity/electrophilicity when provided with either a bond-line, ball-and-stick, or electrostatic potential map for molecular representation
Education in organic chemistry is highly reliant on molecular representations. Students abstract information from representations to make sense of submicroscopic interactions. This study investigates relationships between differing representations: bond-line structures, ball-and-stick, or electrostatic potential maps (EPMs), and predicting partial charges, nucleophiles, and electrophiles. The study makes use of students’ answers in hot-spot question format, where they select partially charged atoms on the image of a molecule and explanations. Analysis showed no significant difference among students when predicting a partially positive atom with each representation; however, more students with EPMs were able to correctly predict the partially negative atom. No difference was observed across representations in students predicting electrophilic character; while representations did influence students identifying nucleophilic character. The affordance of EPMs was that they cued more students to cite relative electronegativity indicating that such students were able to recognize the cause for electron rich/poor areas. This recognition is central to rationalizing mechanisms in organic chemistry. This study offers implications on incorporating EPMs during instruction and provides evidence-based support in how EPMs could be useful in promoting learning on topics that relate to an uneven charge distribution.
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- Award ID(s):
- 2142324
- PAR ID:
- 10505040
- Publisher / Repository:
- Royal Society of Chemistry
- Date Published:
- Journal Name:
- Chemistry Education Research and Practice
- Volume:
- 25
- Issue:
- 1
- ISSN:
- 1109-4028
- Page Range / eLocation ID:
- 343 to 359
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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Accepted Manuscript1.0
- Journal Article:
- https://doi.org/10.1039/D3RP00173C
