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.
more »
« less
How ordering concrete and abstract representations in intermolecular force chemistry tasks influences students’ thought processes on the location of dipole–dipole interactions
Representations in chemistry are the tools by which students, instructors, and chemists reason with chemical concepts that are abstract. Although representations are regularly used within the chemistry classroom, there is more to uncover regarding the ways students interact with representations when given chemistry tasks. This study aimed to address this gap in knowledge. In this study, eighteen students enrolled in second semester general chemistry were recruited for data collection. Semi-structured interviews were utilized to observe how students approached a similar set of dipole–dipole interaction tasks when given four distinct representations. Analysis of the data revealed that students’ approaches to these tasks were affected by the newly explicit features present within each representation. Additionally, the ordering in which the representations were presented to the students influenced the specific features students took notice of and implemented into their approaches to the tasks. These findings can better inform instruction and future research involving chemical representations such that students will form a solid foundation in working with and pulling relevant information from various representations when solving chemistry tasks.
more »
« less
- Award ID(s):
- 2142324
- PAR ID:
- 10505036
- Publisher / Repository:
- Royal Society of Chemistry
- Date Published:
- Journal Name:
- Chemistry Education Research and Practice
- ISSN:
- 1109-4028
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
More Like this
-
-
Electrostatic potential maps (EPM) have the potential to support organic chemistry students in seeing reaction mechanisms through the perspective of electrostatic attraction. Prior to any pedagogical changes, foundational knowledge on how students use EPMs in particular contexts would be needed to inform how to integrate EPMs into instruction. This study describes an exploration into how organic chemistry students use EPMs during two card sort tasks. Seventeen undergraduate organic chemistry students participated in an interview that included an open and closed card sort. The interviews were inductively coded to identify students’ usage of EPMs, and usage change based on the open sort compared to the closed sort. Viewed from a resources framework, this study demonstrated how students’ use of EPMs shifted depending on the task structure. Variations were observed both among students and within students between tasks in terms of whether EPMs were utilized and when utilized whether information from EPMs were used in isolation or integrated with other chemistry concepts. The results of this study imply that more formal integration of EPMs into instruction and assessment would be needed for students who did not use EPMs. Instruction that models and assesses translation of representations may begin activating a more integrated perspective of EPMs which could be productive for students who had an isolated use of EPMs. The introduction of EPMs independent of specific chemistry tasks (e.g.during a general introduction of molecular representations) could lead some students to focus only on explicit features of the EPM representation and not tie features of the representation to their existing chemical knowledge.more » « less
-
In previous work with thermally robust salts [Cassity et al., Phys. Chem. Chem. Phys. , 2017, 19 , 31560] it was noted that an increase in the dipole moment of the cation generally led to a decrease in the melting point. Molecular dynamics simulations of the liquid state revealed that an increased dipole moment reduces cation–cation repulsions through dipole–dipole alignment. This was believed to reduce the liquid phase enthalpy, which would tend to lower the melting point of the IL. In this work we further test this principle by replacing hydrogen atoms with fluorine atoms at selected positions within the cation. This allows us to alter the electrostatics of the cation without substantially affecting the sterics. Furthermore, the strength of the dipole moment can be controlled by choosing different positions within the cation for replacement. We studied variants of four different parent cations paired with bistriflimide and determined their melting points, and enthalpies and entropies of fusion through DSC experiments. The decreases in the melting point were determined to be enthalpically driven. We found that the dipole moment of the cation, as determined by quantum chemical calculations, is inversely correlated with the melting point of the given compound. Molecular dynamics simulations of the crystalline and solid states of two isomers showed differences in their enthalpies of fusion that closely matched those seen experimentally. Moreover, this reduction in the enthalpy of fusion was determined to be caused by an increase in the enthalpy of the crystalline state. We provide evidence that dipole–dipole interactions between cations leads to the formation of cationic domains in the crystalline state. These cationic associations partially block favourable cation–anion interactions, which are recovered upon melting. If, however, the dipole–dipole interactions between cations is too strong they have a tendency to form glasses. This study provides a design rule for lowering the melting point of structurally similar ILs by altering their dipole moment.more » « less
-
Reaction mechanisms are a difficult and foundational topic students encounter in organic chemistry. Consequently, students often memorize when attempting to learn the array of organic reactions. While interventions have been offered to encourage mechanistic reasoning as an alternative approach, a deeper struggle pertaining to students’ comprehension of the underlying chemical principles driving reaction mechanisms is still prevalent. In this study, electrostatic potential maps (EPMs) were explored as a tool students could use to reason with some of these principles to predict and explain the outcomes of a reaction. Through semistructured interviews, 19 students’ sense-making strategies were recorded and analyzed to uncover how they used the features of EPMs with concealed atomic identities and how they reconciled their answers once the identities were made explicit. Analysis revealed that the absence of atomic identities generated approaches centered around electron densities and their utility in predicting reaction mechanisms and outcomes. As the atomic identities were revealed, the majority of participants reverted to memorized mechanisms, while six participants attempted to relate the atomic identities to the interactions of the electron densities. These findings suggest utility in implementing EPMs in the organic chemistry curriculum and offer a feasible intervention to promote sense-making when students reason with organic reactions.more » « less
-
Studies investigating chemistry students’ understanding of intermolecular forces have listed alternative conceptions; however, there is a call to investigate why students might have these alternative conceptions. This study describes how second semester general chemistry students predict the location of dipole–dipole forces between two molecules from a resource activation perspective. During interviews, 18 students were asked to describe the location of forces between four pairs of molecules. Students relied on one or more of the following approaches in determining location: (1) attraction between opposite charges, (2) electronegativity differences, (3) biggest electronegativity values, (4) largest atomic size, and (5) molecular shape. Each student’s approach is characterized by the resources being activated and, in particular, students’ use of electronegativity. Students’ use of electronegativity varied, including comparing electronegativity values between unbonded atoms within a molecule and between atoms present on different molecules. The findings suggest future research directions and teaching implications that could improve students’ understanding of intermolecular forces including the explicit integration and assessment of the concepts of electronegativity and intermolecular forces.more » « less
An official website of the United States government

