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.

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.

scholarly journals Eliciting Student Thinking About Acid-Base Reactions via App and Paper-Pencil Based Problem Solving

2019 ◽  
Author(s):  
Michael N. Petterson ◽  
Field M. Watts ◽  
Emma P. Snyder-White ◽  
Sabrina R. Archer ◽  
Ginger V. Shultz ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Undergraduate Students ◽  
Reaction Mechanisms ◽  
Student Thinking ◽  
Chemical Information ◽  
Acid Base ◽  
First Semester ◽  
Instruction And Learning ◽  
Educational Applications ◽  
Support Students

Research has demonstrated that students often struggle with learning acid-base reaction mechanisms in organic chemistry. One response is the development of educational applications to support instruction and learning. However, research is needed to characterize how the modality influences students’ thinking about acid-base reaction mechanisms. This study used think-aloud interviews conducted with undergraduate students in their first semester of organic chemistry to understand how they worked through acid-base reactions using either paper-pencil or an app. Analysis of the interviews indicates that students recognize the steps of acid-base reactions, but do not always apply the underlying concepts when determining how a reaction will proceed. The modality somewhat influenced students’ thinking, in that the app prevented students from making chemically unreasonable mistakes. However, some students relied on the cues it provided, which could potentially be problematic when they are required to respond to assessments that do not provide these cues. Our results suggest that instructors should emphasize the conceptual grounding for the rules and steps that govern acid-base reactions to promote chemical thinking about the relationships between the reaction components and how those influence reaction outcomes, as well as support students to think critically about the chemical information contained within the modalities they are using.

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.

Using Whiskey-Flavoring Compounds To Teach Distillation and IR Spectroscopy to First-Semester Organic Chemistry Students

2013 ◽  
Vol 91 (1) ◽  
pp. 123-125 ◽  
Author(s):  
Hayley Wan ◽  
Nada Djokic ◽  
Brenna Arlyce Brown ◽  
Yonghoon Kwon
Keyword(s):  
Organic Chemistry ◽  
Ir Spectroscopy ◽  
First Semester ◽  
Chemistry Students

Eliciting student thinking about acid–base reactions via app and paper–pencil based problem solving

2020 ◽  
Vol 21 (3) ◽  
pp. 878-892 ◽  
Author(s):  
Michael N. Petterson ◽  
Field M. Watts ◽  
Emma P. Snyder-White ◽  
Sabrina R. Archer ◽  
Ginger V. Shultz ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Undergraduate Students ◽  
Reaction Mechanisms ◽  
Student Thinking ◽  
Chemical Information ◽  
Acid Base ◽  
First Semester ◽  
Instruction And Learning ◽  
Educational Applications ◽  
Support Students

An understanding of acid–base reactions is necessary for success in chemistry courses and relevant to careers outside of chemistry, yet research has demonstrated that students often struggle with learning acid–base reaction mechanisms in organic chemistry. One response to this challenge is the development of educational applications to support instruction and learning. The development of these supports also creates an opportunity to probe students’ thinking about organic chemistry reaction mechanisms using multiple modalities—i.e., using an app interface or the traditional paper–pencil. This study used think-aloud interviews conducted with undergraduate students in their first semester of organic chemistry to understand how they worked through two acid–base reactions using either paper–pencil or an app. Analysis of the interviews indicates that students from both groups recognize the steps of acid–base reactions, but do not always apply the underlying concepts, such as assessment of pKa values or resonance, when determining how a reaction will proceed. The modality seemed to somewhat influence students’ thinking, as the app prevented students from making chemically unreasonable mistakes. However, some students relied on the cues it provided, which could potentially be problematic when they are required to respond to assessments that do not provide these cues. Our results suggest that instructors should emphasize the conceptual grounding for the steps that govern acid–base reactions to promote chemical thinking about the relationships between the reaction components and how those influence reaction outcomes, as well as support students to think critically about the chemical information contained within the modalities they are using.

scholarly journals The role of guidance in student engagement with chemistry studies

2019 ◽  
Vol 7 (1) ◽  
Author(s):  
Piia Valto ◽  
Piia Nuora
Keyword(s):  
Student Engagement ◽  
Study Skills ◽  
First Year ◽  
First Semester ◽  
Chemistry Students ◽  
Orientation Course ◽  
Students First ◽  
Extensive Effort ◽  
The University

During recent years, the Department of Chemistry at the University of Jyväskylä has made an extensive effort to support chemistry students’ first study year. The first-year curriculum includes enhanced study counselling course, intensive orientation course and support for academic study skills via a specific course.  In this study, the effects of the revisions were studied by exploring the chemistry students study continuation and what factors contributed to it.  In 2015 to 2017, data were collected from first-year chemistry students (n = 106), who completed a questionnaire at the beginning and at the end of their first semester. The results show that the percentage of dropout rates after the first year decreased. Students’ current challenges are different than they have been previously, thus putting new demands on their guidance. The results of the study indicate that students value guidance and study counselling especially at the beginning of their studies.

Development and evaluation of a Lewis acid–base tutorial for use in postsecondary organic chemistry courses

2019 ◽  
Vol 97 (10) ◽  
pp. 711-721 ◽  
Author(s):  
Amber J. Dood ◽  
Kimberly B. Fields ◽  
Daniel Cruz-Ramírez de Arellano ◽  
Jeffrey R. Raker
Keyword(s):  
Organic Chemistry ◽  
Lewis Acid ◽  
Positive Impact ◽  
Summative Assessment ◽  
Response Assessment ◽  
Acid Base ◽  
Constructed Response ◽  
First Semester ◽  
Chemistry Students ◽  
Instructional Contexts

A well-developed understanding of the Lewis acid–base model is highly important for the understanding of organic chemistry. As such, students should receive instruction and be assessed on use of the model. Online tutorials and constructed-response items provide a means for confirming that students have a well-developed conceptualization of the Lewis acid–base model. In a prior study, a predictive logistic regression model was presented that can be used with constructed-response assessment items to determine use of a Lewis acid–base model in written responses. In this study, we use that predictive model to evaluate the effectiveness of a tutorial designed to promote meaningful understanding of the Lewis acid–base model in three different instructional contexts: first-semester organic chemistry students before summative assessment, first-semester organic chemistry students after summative assessment, and second-semester organic chemistry students. Additionally, we evaluated the learning gains of one set of first-semester students after a 3-week time delay. McNemar’s test results suggest that the tutorial had a net positive impact in all three instructional contexts, with the most significant impact observed with the second-semester students. This work has implications for further development of literature-based tutorials to promote meaningful understanding of organic chemistry reaction mechanisms assessed by constructed-response items.

scholarly journals Utilizing Rasch analysis to establish the psychometric properties of a concept inventory on concepts important for developing proficiency in organic reaction mechanisms

2019 ◽  
Vol 0 (0) ◽  
Author(s):  
Sachin Nedungadi ◽  
Sue H. Paek ◽  
Corina E. Brown
Keyword(s):  
Organic Chemistry ◽  
Reaction Mechanisms ◽  
Rasch Analysis ◽  
Large Scale ◽  
Assessment Tool ◽  
Validity And Reliability ◽  
Organic Reaction ◽  
First Semester ◽  
Chemistry Students ◽  
Organic Reaction Mechanisms

AbstractUndergraduate organic chemistry has been found to be historically difficult for students and one area where students struggle is organic reaction mechanisms. The difficulties students face with reaction mechanisms has been a source of interest in chemical education research but most studies done have been purely qualitative. An assessment tool that could be used on a large-scale for instructors to gauge the difficulties their students face, would be useful. The aim of this pilot study is to use Rasch analysis to establish the validity and reliability of the concepts important for developing proficiency in organic reaction mechanisms inventory (RMCPI). The test, containing 25 items, was administered to first semester organic chemistry students (N = 44) at a mid-sized university. The data was analyzed using Rasch techniques to explore the dimensionality of the instrument, the difficulty of the items, the item fit, and the reliability. The results indicate that the instrument is unidimensional and most of the items fit well to the dichotomous Rasch model. The test was found to be difficult and this will be explored further by increasing the sample size, administering the test to students from other universities and increasing the number of items on the inventory.

scholarly journals Development and psychometric analysis of an inventory of fundamental concepts for understanding organic reaction mechanisms

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Sachin Nedungadi ◽  
Michael D. Mosher ◽  
Sue Hyeon Paek ◽  
Richard M. Hyslop ◽  
Corina E. Brown
Keyword(s):  
Organic Chemistry ◽  
Reaction Mechanisms ◽  
Test Theory ◽  
Psychometric Analysis ◽  
Validity And Reliability ◽  
Organic Reaction ◽  
First Semester ◽  
Chemistry Students ◽  
Alternate Conceptions ◽  
Organic Reaction Mechanisms

Abstract The fundamental concepts for organic reaction mechanisms inventory (FC-ORMI) is a multiple-choice instrument designed to assess students’ conception of fundamental concepts for understanding organic reaction mechanisms. The concepts were identified from open-ended interviews and a national survey of organic chemistry instructors reported in a previous study. This manuscript describes the development of the inventory items related to these identified concepts and the psychometric analysis of the instrument. In the developmental stage, open-ended questions were administered to first-semester organic chemistry students (N = 138), and open-ended interviews were conducted with students (N = 22) from the same pool to gain insight into their thought processes. The answers revealed alternate conceptions which were used to formulate distractors for the inventory. A pilot version and a beta version of the inventory were administered to 105 and 359 first-semester organic chemistry students, respectively. From these administrations, the 26-item alpha version was developed and administered to first-semester undergraduate organic chemistry students (N = 753). Psychometric analysis was conducted at the item and test level using Classical Test Theory and Rasch analysis. The results indicate that the items on the FC-ORMI function well to reveal students’ alternate conceptions. The instrument meets the acceptable standards of validity and reliability for concept inventories.

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