Patterns of reactions: a card sort task to investigate students’ organization of organic chemistry reactions

2019 ◽  
Vol 20 (1) ◽  
pp. 30-52 ◽  
Author(s):  
Kelli R. Galloway ◽  
Min Wah Leung ◽  
Alison B. Flynn
Keyword(s):  
Organic Chemistry ◽  
Structural Features ◽  
Formative Assessments ◽  
Chemistry Curriculum ◽  
Card Sort ◽  
Chemistry Students ◽  
New Curriculum ◽  
Sorting Process ◽  
Specific Reactions ◽  
The University

Research has shown that within a traditional organic chemistry curriculum, organic chemistry students struggle to develop deep conceptual understanding of reactions and attribute little meaning to the electron-pushing formalism. At the University of Ottawa, a new curriculum was developed for organic chemistry in which students are taught the language of the electron-pushing formalism prior to learning about specific reactions. Reactions are then organized by governing pattern of mechanism rather than by functional group and are taught in a gradient of complexity. To investigate how students are making connections across reactions within the new curriculum, a card sort task was developed. The card sort task consisted of 25 cards, each depicting the reactants and solvent for a reaction taught during the two-semester organic chemistry sequence. The first part of the task asked participants to sort 15 of 25 cards into categories. Then, participants were given the 10 remaining cards to incorporate into categories with the previous 15. Participants were asked to explain the characteristics of each category and their sorting process. Students (N= 16) in an organic chemistry course were interviewed while enrolled in the second semester course. We analyzed the students’ sorts based on which cards were sorted frequently together, the underlying characteristics used to form the categories, and the participants’ sorting processes. Participants created categories based on different levels of interpreting the reactions on the cards, with levels ranging from recognizing identical structural features to identifying similar types of mechanisms. Based on this study, if we want students to develop mechanistic thinking, we think students need to be more explicitly directed to the patterns present in organic reaction mechanisms and given opportunities to uncover and identify patterns on their own, during both summative and formative assessments.

Students’ interpretations of mechanistic language in organic chemistry before learning reactions

2017 ◽  
Vol 18 (2) ◽  
pp. 353-374 ◽  
Author(s):  
Kelli R. Galloway ◽  
Carlee Stoyanovich ◽  
Alison B. Flynn
Keyword(s):  
Organic Chemistry ◽  
Student Thinking ◽  
Reaction Step ◽  
First Semester ◽  
Chemistry Students ◽  
Interview Guide ◽  
Specific Reactions ◽  
Teaching Learning ◽  
The University ◽  
Constant Comparative Analysis

Research on mechanistic thinking in organic chemistry has shown that students attribute little meaning to the electron-pushing (i.e., curved arrow) formalism. At the University of Ottawa, a new curriculum has been developed in which students are taught the electron-pushing formalism prior to instruction on specific reactions—this formalism is part of organic chemistry's language. Students then learn reactions according to the pattern of their governing mechanism and in order of increasing complexity. If students are fluent in organic chemistry's language, they should have lower cognitive load demands when learning new reactions, and be better positioned to connect the three levels of chemistry's triplet (i.e., Johnstone's triangle). We developed a qualitative research protocol to explore how students use and interpret the mechanistic language. Twenty-nine first-semester organic chemistry students were interviewed, in which they were asked to (1) explain a mechanism, given all the starting materials, intermediates, products, and electron-pushing arrows, (2) draw in arrows for a reaction mechanism, given the starting materials and products of each step, and (3) predict the product of a reaction step, given the starting materials and electron-pushing arrows for that step. To investigate the students’ ideas about mechanistic language rather than their knowledge of specific reactions, we selected reactions for the interview guide that had not yet been taught. Following transcription, we analyzed the interviews using constant comparative analysis to explore how students used and interpreted the mechanistic language. Four categories of student thinking emerged with electron movement underlying students’ thinking throughout the interviews. Herein, we discuss these categories, students’ interpretation of the symbolism, connections to learning theory, and implications for teaching, learning, and research.

Exploring Student Thinking About Addition Reactions

2020 ◽  
Author(s):  
Solaire Finkenstaedt-Quinn ◽  
Field M. Watts ◽  
Michael N. Petterson ◽  
Sabrina R. Archer ◽  
Emma P. Snyder-White ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Student Thinking ◽  
Addition Reactions ◽  
Think Aloud ◽  
Chemistry Curriculum ◽  
Student Reasoning ◽  
Chemistry Students ◽  
Resonance Stabilization ◽  
Paper And Pencil ◽  
Minimal Research

While student reasoning about many of the reaction types covered in the organic chemistry curriculum have been studied previously, there is minimal research focused specifically on how students think about the mechanisms of addition reactions. This study addresses that gap by probing organic chemistry students’ thinking using think-aloud interviews as they worked through two different addition reactions. Students worked through the mechanisms using either paper and pencil or an app that dynamically represents the molecules. Overall, students were able to identify the steps of the two addition reactions but did not always successfully apply chemical thinking during the mechanistic steps. Specifically, both groups of students struggled with the concepts related to carbocation stability, frequently misapplying stabilization via substitution and demonstrating difficulty in identifying the potential for resonance stabilization. Our results suggest that instructors should emphasize the conceptual grounding directing mechanistic steps, in particular when determining carbocation stability.

Exploring Student Thinking About Addition Reactions

2020 ◽  
Author(s):  
Solaire Finkenstaedt-Quinn ◽  
Field M. Watts ◽  
Michael N. Petterson ◽  
Sabrina R. Archer ◽  
Emma P. Snyder-White ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Student Thinking ◽  
Addition Reactions ◽  
Think Aloud ◽  
Chemistry Curriculum ◽  
Student Reasoning ◽  
Chemistry Students ◽  
Resonance Stabilization ◽  
Paper And Pencil ◽  
Minimal Research

While student reasoning about many of the reaction types covered in the organic chemistry curriculum have been studied previously, there is minimal research focused specifically on how students think about the mechanisms of addition reactions. This study addresses that gap by probing organic chemistry students’ thinking using think-aloud interviews as they worked through two different addition reactions. Students worked through the mechanisms using either paper and pencil or an app that dynamically represents the molecules. Overall, students were able to identify the steps of the two addition reactions but did not always successfully apply chemical thinking during the mechanistic steps. Specifically, both groups of students struggled with the concepts related to carbocation stability, frequently misapplying stabilization via substitution and demonstrating difficulty in identifying the potential for resonance stabilization. Our results suggest that instructors should emphasize the conceptual grounding directing mechanistic steps, in particular when determining carbocation stability.

scholarly journals Integrating Course Material and Application: A Progressive Writing Assignment Applied to an Astrochemistry Tutorial

2018 ◽  
Vol 2 (1) ◽  
Author(s):  
Olivia H Wilkins ◽  
Camillus F Buzard
Keyword(s):  
General Chemistry ◽  
Graduate Students ◽  
Chemistry Curriculum ◽  
Chemistry Students ◽  
Research Areas ◽  
Broader Impacts ◽  
Big Picture ◽  
Course Material ◽  
Writing Assignment ◽  
The Subject

A major challenge in teaching is helping students integrate course concepts to understand the big picture of a field and apply those concepts in new situations. To address this challenge in a tutorial course about astrochemistry (taught by graduate students to chemistry undergraduates), we implemented a progressive writing assignment that culminated in a final presentation. In the progressive writing assignment, students chose an astrochemistry topic they found interesting to be the subject of three sequential papers, which became the basis for their presentations. The purpose of this assignment was to gradually introduce chemistry students to research areas in astronomy, which is by nature outside the general chemistry curriculum, while also providing students with regular feedback. Over the course of the assignment, students applied key themes in the course—significance of astrochemistry research, research methods, and chemistry in astronomical environments—separately to their chosen topics before explaining in the final presentation how these different aspects of astrochemistry work together. By incorporating stories and anaologies, rather than just facts, students gave presentations that were accessible to a novice audience. As a result, students explained broader impacts of astrochemistry research, rather than just focusing on results, and they entertained questions with answers that went beyond clarification of the material discussed.

scholarly journals Modeling Humanizing Education Through Newly Reviewed Materials Engineering Curriculum

2021 ◽  
Vol 9 (3) ◽  
pp. 63-79
Author(s):  
Norshahida Sarifuddin ◽  
Zuraida Ahmad ◽  
Ahmad Zahirani Ahmad Azhar ◽  
Hafizah Hanim Mohd Zaki ◽  
Amelia Wong Azman ◽  
...  
Keyword(s):  
Engineering Education ◽  
Curriculum Design ◽  
Well Being ◽  
Engineering Programs ◽  
Academic Field ◽  
Materials Engineering ◽  
New Curriculum ◽  
Humanitarian Engineering ◽  
Definition Of ◽  
The University

In line with the current global focus on sustainability and the well-being of the planet, becoming a professional engineer nowadays requires more than simple mastery of technical skills. Considering that engineers are required to have a deep sense of responsibility not only for humankind but also for the environment, engineering education and practices must be reformed substantially to prepare engineers that will contribute to sustainable development. This necessitates updating conventional engineering programs (CEE) to incorporate Humanizing Engineering Education (HEE). Although HEE is an old practice of individual engineers and other organizations outside the academic field, it is relatively new in academic engineering. While the definition of what truly merits being considered HEE remains debatable, many engineers believe that their work involves a humanitarian aspect. To streamline the development of HEE, there is a need for developing guidelines and frameworks for a comprehensive model. Ideally, that framework should integrate humanizing pedagogy in the new curriculum design. The objective of the paper is to share the experience of the authors in designing a new curriculum for a Materials Engineering Programme (MEP) that is embedded with Humanitarian Engineering (HE), which is among the main elements of HEE. Data collection was through interviews, qualitative surveys, reports from the stakeholders, accreditation bodies and benchmarking with other Higher Learning Institutions (HLI). An extensive scholarly literature review was executed to identify shortcomings in CEE and how it could be reformed by integrating it with HEE. The Sejahtera Academic Framework (SAF); a strategic framework for academic programmes developed by the university, was used as a reference to customize MEP to better meet students’ needs. Since the proposed model applies a new emerging concept, it inevitably raises challenges related to different levels of understanding among course implementers and perceptions of external stakeholders. Moreover, the developers had to consider the limitations imposed by the university's policies and structures while acknowledging the availability of finite resources (i.e. time, money, equipment, and expertise).

The role of authentic contexts and social elements in supporting organic chemistry students’ interactions with writing-to-learn assignments

2021 ◽  
Author(s):  
Michael N. Petterson ◽  
Solaire A. Finkenstaedt-Quinn ◽  
Anne Ruggles Gere ◽  
Ginger V. Shultz
Keyword(s):  
Organic Chemistry ◽  
Peer Interactions ◽  
Careful Consideration ◽  
Writing To Learn ◽  
Student Interest ◽  
Student Interactions ◽  
Course Content ◽  
Chemistry Students ◽  
Student Affect ◽  
Survey Responses

Student affect is an important factor in the learning process and may be especially important in gateway courses such as organic chemistry. Students’ recognition of the relevance of the content they are learning and interactions with their peers can support their motivation to learn. Herein, we describe a study focused on how Writing-to-Learn assignments situate organic chemistry content within relevant contexts and incorporate social elements to support positive student interactions with organic chemistry. These assignments incorporate rhetorical elements—an authentic context, role, genre, and audience—to support student interest and demonstrate the relevance of the content. In addition, students engage in the processes of peer review and revision to support their learning. We identified how the authentic contexts and peer interactions incorporated into two Writing-to-Learn assignments supported students’ interactions with the assignments and course content by analyzing student interviews and supported by feedback survey responses. Our results indicate that assignments incorporating these elements can support student affect and result in students’ perceived learning, but that there should be careful consideration of the relevance of the chosen contexts with respect to the interests of the students enrolled in the course and the complexity of the contexts.

Introduction: Why oxygen chemstry?

1992 ◽  
Author(s):  
Donald T. Sawyer ◽  
R. J. P. Williams
Keyword(s):  
Organic Chemistry ◽  
Nineteenth Century ◽  
Chemical Properties ◽  
First Year ◽  
Chemistry Curriculum ◽  
Design And Synthesis ◽  
Carbon Molecules ◽  
Living Organisms ◽  
Fixed Array ◽  
Oxygen Atoms

The fundamental premise of chemistry is that all matter consists of molecules. The physical and chemical properties of matter are those of the constituent molecules, and the transformation of matter into different materials (compounds) is the result of their reactions to form new molecules. A molecule consists of two or more atoms held in a relatively fixed array via valence-electron orbital overlap (covalent bonds; chemical bonds). In the nineteenth century chemists focused on the remarkable diversity of molecules produced by living organisms, which have in common the presence of tetravalent carbon atoms. As a result the unique versatility of carbon for the design and synthesis of new molecules was discovered, and the subdiscipline of organic chemistry (the science of carbon-containing molecules) has become the dominant part of the discipline. Clearly, the results from a focus on carbon-based chemistry have been immensely useful to science and to society. Although most molecules in biological systems [and produced by living organisms (particularly aerobic systems)] contain oxygen atoms as well as carbon and hydrogen (e.g., proteins, nucleic acids, carbohydrates, lipids, hormones, and vitamins), there has been a long tradition in all of chemistry to treat oxygen atoms as “neutral counterweights” for the “important,” character-determining elements (C, H, Al, Si, Fe, I) of the molecule. Thus, chemists have tended to take the most important element (oxygen) for granted. The chemistry curriculum devotes one or two year-courses to the chemistry of carbon (“Organic Chemistry”), but only a brief chapter on oxygen is included in the first-year and the inorganic courses. However, if the multitude of hydrocarbon molecules is from the incorporation of oxygen atoms in single-carbon molecules argues against the assignment of a “neutral character” for oxygen atoms [e.g., Cn(graphite), CH4(g), CH3OH(1), CH2(O)(1), HC(O)OH(1), (HO)2C(O)(aq), CO(g), CO2(g)]. Just as the focus of nineteenth century chemists on carbon-containing molecules has produced revolutionary advances in chemical understanding, and yielded the technology to synthesize and produce useful chemicals, polymers, and medicinals; I believe that a similar focus on oxygen chemistry is appropriate and will have analogous rewards for chemistry, biochemistry, and the chemical process technologies.

Heteroaromatic Construction: The Fukuyama Synthesis of Tryprostatin A

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Organic Chemistry ◽  
University Of California ◽  
University Of Arkansas ◽  
Yale University ◽  
Au Catalyst ◽  
University Of Houston ◽  
Selective Substitution ◽  
Mcgill University ◽  
La Jolla ◽  
The University

Alessandro Palmieri of the University of Camerino developed (Synlett 2010, 2468) the condensation of a nitro acrylate 1 with a 1,3-dicarbonyl partner 2 to give the furan 3. Chaozhong Li of the Shanghai Institute of Organic Chemistry showed (Tetrahedron Lett. 2010, 51, 3678) that an alkenyl halide 4 could be cyclized to the furan 5. Ayhan S. Demir of Middle East Technical University established (Chem. Commun. 2010, 46, 8032) that a Au catalyst could catalyze the addition of an amine 7 to a cyanoester 6 to give the pyrrole 8 . Bruce A. Arndtsen of McGill University effected (Org. Lett. 2010, 12, 4916) the net three-component coupling of an imine 9, an acid chloride 10, and an alkyne 11 to deliver the pyrrole 12. Bernard Delpech of CNRS Gif-sur-Yvette prepared (Org. Lett. 2010, 12, 4760) the pyridine 15 by combining the diene 13 with the incipient carbocation 14. Max Malacria, Vincent Gandon, and Corinne Aubert of UPMC Paris optimized (Synlett 2010, 2314) the internal Co-mediated cyclization of a nitrile alkyne 5 to the tetrasubstituted pyridine 17. Yoshiaki Nakao of Kyoto University and Tamejiro Hiyama, now at Chuo University, effected (J. Am. Chem. Soc. 2010, 132, 13666) selective substitution of a preformed pyridine 18 at the C-4 position by coupling with an alkene 19. We showed (J. Org. Chem. 2010, 75, 5737) that the anion from deprotonation of a pyridine 21 could be added in a conjugate sense to 22 to give 23. Other particularly useful strategies for further substitution of preformed pyridines have been described by Olafs Daugulis of the University of Houston (Org. Lett. 2010, 12, 4277), by Phil S. Baran of Scripps/La Jolla (J. Am. Chem. Soc. 2010, 132, 13194), and by Robert G. Bergmann of the University of California, Berkeley, and Jonathan A. Ellman of Yale University (J. Org. Chem. 2010, 75, 7863). K. C. Majumdar of the University of Kalyani developed (Tetrahedron Lett. 2010, 51, 3807) the oxidative Pd-catalyzed cylization of 24 to the indole 25. Nan Zheng of the University of Arkansas showed (Org. Lett. 2010, 12, 3736) that Fe could be used to catalyze the rearrangement of the azirine 26 to the indole 27.

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