RESEARCH & DEVELOPMENT
An organic chemistry curriculum based on patterns and principles
new organic chemistry curriculum
We developed a new organic curriculum at uOttawa that we have been teaching since 2011. We reorganized the reactions we teach so that they are organized by their governing mechanism. The goal is to help students identify and predict patterns and principles of reactivity rather than memorize.
Organic Chemistry I starts with principles of structure and properties, as do most courses. The main changes come in the reactivity sections. Acid–base chemistry leads off reactivity (part A), following by simple reactions between nucleophiles and pi electrophiles (part B). Those simple reactions are meant to set the groundwork of principles of reactivity. Next come reactions of pi nucleophiles with electrophiles (part C), then aromatic nucleophiles with electrophiles (Part D). In parts C and D, students begin to learn about competing mechanistic pathways (regioselectivity).
Organic Chemistry II is next. In this course, students learn more about competing mechanistic pathways (part E), including the mechanistic parallels between E2 and oxidation reactions. Part F extends the reactivity principles of part B, by adding leaving groups (including the “hidden” leaving groups of acetals and analogs). Finally, Part G brings together reactivity from throughout the course, including the augmented pi nucleophiles (enols, enolates, and analogs) to extend Part C and various electrophiles. Spectroscopy is addressed between parts E and F.
The organic chemistry curriculum at the University of Ottawa has been redesigned to incorporate a patterns-of-mechanisms model in place of a functional group one. The curriculum emphasizes mechanistic patterns and chemistry principles and is organized in a gradient of difficulty.
learn more about the curriculum
Flynn, A. B.; Ogilvie, W. W. “Mechanisms before reactions: A mechanistic approach to the organic chemistry curriculum based on patterns of electron flow” J. Chem. Educ. 2015, 92(5), 803–810.
patterns of Mechanisms research
The organic chemistry curriculum at uOttawa is taught based on the governing pattern of mechanism. One of the goals of this organization is to help students to be able to make connections between reactions with different structural features but similar mechanisms. If students are able to identify mechanistic patterns between reactions, then the need for memorizing individual reactions is reduced. Although the curriculum is organized by pattern of mechanism, we need to collect evidence for how students are perceiving (or not) connections between organic reactions. We have developed a card sort task to explore how students are organizing their knowledge of organic reactions. The results from this study will provide evidence for how to design instruction to help students be able to identify mechanistic patterns across organic reactions.
Big picture overview of our mechanistic patterns research
Chemistry education research details of our mechanistic patterns work
Learn more about the research
Galloway, K. R., Leung, M. W., & Flynn, A. B. "Patterns of Reactions: A card sort task to investigate students’ organization of organic chemistry reactions." Chem Educ. Res. Pract. 2018, ASAP .
Galloway, K. R., Leung, M. W., & Flynn, A. B. "A Comparison of How Undergraduates, Graduate Students, and Professors Organize Organic Chemistry Reactions" J. Chem. Educ. 2018 95 (3), 355-365.
Galloway, K. R.; Stoyanovich, C.; Flynn, A. B. "Students’ interpretations of mechanistic language in organic chemistry before learning reactions" Chem. Educ. Res. Pract. 2017, 18, 353.
Flynn, A. B.; Featherstone, R. B. "Language of mechanisms: exam analysis reveals students' strengths, strategies, and errors when using the electron-pushing formalism (curved arrows) in new reactions" Chem. Educ. Res. Pract. 2017, 18, 64.
Online Learning Tools
We created OrgChem101 to help students learn fundamental concepts in organic chemistry, including its language (nomenclature and arrow symbolism) and acid–base chemistry. OrgChem101 is free for anyone to use, and includes three modules: Organic Nomenclature, Organic Mechanisms, and Acid–Base Reactions.
Organic chemistry nomenclature
The Organic Nomenclature module is a FREE, bilingual, online, interactive learning tool designed to help students learn organic chemistry nomenclature. With this learning tool, students can draw organic molecules, name organic molecules, and identify key functional groups. There are hints to guide students along the way. Best of all, we describe the relevance of these molecules in our everyday lives!
Through our research, we found that students had high learning gains in a short period of time when they used the nomenclature module. Students also reported an excellent learning experience.
Read more
Bodé, N. E., Caron, J., & Flynn, A. B. Evaluating students’ learning gains and experiences from using nomenclature101.com. 2016, Chem. Educ. Res. Prac., 17(4), 1156–1173.
Here’s an article about the project written by Tyler Irving for the Canadian Chemical News (January 2012 issue): ACCN article.pdf and a more recent one: Organic chemistry students get online support for knowledge gap. ACCN, July/Aug 2014 issue, page 42.
Visser, R. Flynn, A. (2018). Developing Open Educational Resources in French and English for Students of Organic Chemistry at the University of Ottawa, Canada. Retrieved from https://teachonline.ca/pockets-innovation/developing-open-educational-resources-french-and-english-students-organic-chemistry-university on July 16th.
organic reaction mechanisms
The Organic Reaction Mechanisms module aims to provide students with a learner-controlled way to master organic chemistry’s language: the electron-pushing (curved arrow) formalism.
Students can learn the formalism in a short period of time when using the tool, as we discovered in our study of student learning: Carle, M. S.; Visser, R.; Flynn, A. B. “Evaluating students’ learning gains, strategies, and errors using OrgChem101’s Module: Organic Mechanisms — Mastering the arrows” Chem. Educ. Res. Pract. 2020, Advance Article.
Learning outcomes (LOs) and key principles associated with the Organic Mechanisms Module
Read more
Stoyanovich, C. M.; Gandhi, A.; and Flynn, A. B. “Acid–Base Learning Outcomes for Students in an Introductory Organic Chemistry Course” J. Chem. Educ. 2015, 92 (2), 220–229.
Flynn, A. B. and Amellal, D.G. “Chemical Information Literacy: pKa Values—Where Do Students Go Wrong?” J. Chem. Educ. 2016, 93 (1), 39–45.
Nomenclature101.com team: Gisèle Richard, Richard Pinet, Alison Flynn, Melissa Daviau-Duguay, Caroline Marcoux, Jeanette Caron, Jamey Laroche
This online learning tool was created through a collaboration with the Centre for Innovative Pedagogies and Digital Learning (CIPDL)—part of uOttawa’s Teaching and Learning Support Service—and senior undergraduate student Melissa Daviau-Duguay. Our posters from the Canadian Network for Innovation in Education conference (Chem_Poster_CNIE FINAL.pdf) and the International Conference in Chemical Education (Nomenclature101_Poster_ICCE.pdf) explain more.
Organic Chemistry's Language
There are currently two projects related to the evaluation of the patterns of mechanisms curriculum at uOttawa. One project is studying how students interpret and use the language of mechanisms having learned the symbolism, but before learning specific reactions. The second project is investigating how students organize their knowledge of organic reactions.
Video created by Ahmed Youssef. Finalist for uOGRADflix 2022.
Read more
Flynn A. B. & Featherstone, R. “Language of mechanisms: exam analysis reveals students' strengths and errors when using the electron-pushing formalism (curved arrows) in new reactions” Chem. Educ. Res. Pract. 2017, 18, 64–77.
Galloway, K. R., Stoyanovich, C., & Flynn, A. B. “Students’ Interpretations of Mechanistic Language in Organic Chemistry Before Learning Reactions.” Chem. Educ. Res. Pract., 2017, 18, 353–374. DOI: 10.1039/C6RP00231E.
Carle, M.; Visser, R.; Flynn, A. B. Evaluating students’ learning gains, strategies, and errors using OrgChem101’s module: organic mechanisms–mastering the arrows. Chem. Educ. Res. Pract. 2020, 21, 582–596.
Organic Synthesis
The cognitive domain of Bloom’s taxonomy (describes six orders of learning in the form of a pyramid, in which remembering is at the bottom and creating (something new) is at the top. The higher orders of learning require advanced skills such as analysis and problem-solving, as well as incorporating the lower level skills. Retrosynthetic analysis and synthesis require higher order thinking skills and constitute challenges in learning. We are studying how chemistry students learn those higher order skills and the effectiveness of in- and out-of-class teaching & learning activities. One main goal is to help students improve their higher order thinking skills through those targeted learning activities.
We're studying students' strategies and skills in solving organic synthesis problems. We've also developed learning activities that can be used in large or small classes to help students learn those skills. Check out Nik's recent video about our work:
CLASSROOM ACTIVITIES
Flynn, A. B. “Developing Problem-Solving Skills through Retrosynthetic Analysis and Clickers in Organic Chemistry” J. Chem. Educ., 2011, 88 (11), 1496–1500.
Resource from the Baran group: https://www.scripps.edu/baran/images/grpmtgpdf/Gianatassio_Feb_2012.pdf
RESEARCH STUDIES
Flynn, A. B. “How do students work through organic synthesis learning activities?” Chem. Educ. Res. Prac. 2014, 15, 747–762.
Bodé, N. E.; Flynn, A. B. “Strategies of Successful Synthesis Solutions: Mapping, Mechanisms, and More” J. Chem. Educ., 2016, 93 (4), 593–604. An ACS Editor’s Choice article.
Flynn, A. “Problem solving in organic chemistry synthesis” Invited book chapter, RSC Advances in Chemistry Education. In Press. Invited contribution.
Mental models of chemistry
To learn reaction mechanisms in organic chemistry students must understand organic chemistry’s symbolism, make connections between many abstract concepts, and visualize the invisible molecular world. However, the static models that educators use to describe reaction mechanisms poorly represent the dynamic nature of chemistry at the molecular level, where molecules are in constant motion. Animations of organic reaction mechanisms can bring to life the information embedded in these traditional, static representations.
The new organic chemistry curriculum at uOttawa and our online learning platform orgchem101.com use Organic ChemWare animations, created using best practices from the visualization literature. We are investigating how these animations affect student learning at the behavioural and neurological level. To do this, we are conducting studies to compare how static and animated representations of organic chemistry reactions are experienced by the students using eye-tracking technology, and also how they affect patterns of brain activity. In particular, we are interested in how resting state brain activity can predispose an individual’s problem solving abilities and capacity for learning. This mix of neuroscience and educational research allows us to investigate complex questions and will help us improve the quality and effectiveness of animations as learning tools for organic chemistry.
learn more
Bongers, A.; Northoff, G.; Flynn, A. B. Working with Mental Models to Learn and Visualize a New Reaction Mechanism. Chem. Educ. Res. Pract. 2019.
Bongers, A.; Beauvoir, B.; Streja, N.; Northoff, G.; & Flynn, A. B. “Building mental models of a reaction mechanism: the influence of static and animated representations, prior knowledge, and spatial ability” Chem. Educ. Res. Pract. 2020, 2020, 21, 496–512.
Bongers, A.; Flynn, A. B.; & Northoff, G. “Is learning scale-free? Chemistry learning increases EEG fractal power and changes the power law exponent” Neuroscience Research. 2019, 156, 165–177. Invited contribution.
Flipped Courses
I teach most courses in a flipped format. In a flipped course, content that is traditionally delivered in class is moved online, and problem-solving and other learning activities take place in class. For these courses, the lectures are now online and are broken up in short video segments. In-class time is dedicated to problem solving and figuring out more complex topics. Our research found that in a flipped classroom format, students' academic success was significantly higher and failure and withdrawal rates were significantly lower.
Structure of flipped and blended courses
Evaluation of flipped and blended courses
Evaluation findings from the flipped courses
Exam and final grades were higher in the flipped courses than the lecture courses, even when the latter were taught in an active format (i.e., with clicker questions punctuating the lectures). See associated articles for statistical analyses. N = 364 – 1226.
Failure (blue/bottom) and withdrawal (pink/top) rates were lower in the flipped courses compared to the lecture courses. See associated articles for statistical analyses. N = 364 – 1226.
Classroom observations found that students worked actively for more than 3/4 of the flipped class. Q = question. Students’ activities are shown on the left; instructor’s activities are shown on the right. The more passive moments for students are pulled away from the pie.
Our studies
Flynn, A.B. "Structure And Evaluation Of Flipped Chemistry Courses: Organic & Spectroscopy, Large and Small, First To Third Year, English And French" Chemistry Education Research and Practice, 2015, 16, 198-211.
Flynn, A. B. "Flipped chemistry courses: Structure, aligning learning outcomes, and evaluation" Chapter in Online Approaches to Chemical Education. ACS Symposium Series, Vol. 1261. 2017. Chapter 12, pp 151–164. Invited contribution.
Broader research
There is a lot more research being done about active learning methods in the sciences. A central goal is to improve students’ learning. Here are some key papers:
“Students in the active classroom learn more, but they feel like they learn less.”
Deslauriers, L.; McCarty, L. S.; Miller, K.; Callaghan, K.; Kestin, G. Measuring Actual Learning versus Feeling of Learning in Response to Being Actively Engaged in the Classroom. Proc. Natl. Acad. Sci. U. S. A. 2019, 116 (39), 19251–19257.
“Active learning leads to increases in examination performance that would raise average grades by a half a letter, and that failure rates under traditional lecturing increase by 55% over the rates observed under active learning.”
Freeman, S.; Eddy, S. L.; McDonough, M.; Smith, M. K.; Okoroafor, N.; Jordt, H.; Wenderoth, M. P. Active Learning Increases Student Performance in Science, Engineering, and Mathematics. Proc. Natl. Acad. Sci. U. S. A. 2014, 111 (23), 8410–8415.
Handelsman, J.; Ebert-May, D.; Beichner, R.; Bruns, P.; Chang, A.; DeHaan, R.; Gentile, J.; Lauffer, S.; Stewart, J.; Tilghman, S. M.; et al. Scientific Teaching. Science. 2004, 304, 521–522.
Stains, B. M.; Harshman, J.; Barker, M. K.; Chasteen, S. V; Cole, R.; DeChenne-Peters, S. E.; Eagan Jr, M. K.; Esson, J. M.; Knight, J. K.; Laski, F. A.; et al. Anatomy of STEM Teaching in North American Universities. Science (80). 2018, 359 (6383), 1468–1470.
Flipped courses can take place in any location, including active learning classrooms or lecture halls.
Many types of in-class activities are possible
Students voted on the peak assignment for the hydroxyl proton (correct answer: K). In the first vote, most voted “G”, using the heuristic (rule of thumb) that hydroxyl peaks are broad. Before the second vote, they were encouraged to use the 2D spectra (which included a COSY and HMQC). In the second vote, the majority had the correct answer (although many still voted G). Class size: 15 - 150
I handed out 8–10 sticky notes to students around the class (students always have the option to decline). Students drew their answers on sticky notes and handed them in (they could work in groups to generate their answers and did not put their names on their work). A selection of answers is labelled (A, B, C…) and students vote on the answers. Class size: 400
Students brainstormed possible reasons for the observed trend in IR absorption frequencies. Their ideas were labelled (A, B, C) and students voted on the best answer. Often, I also ask them to explain their reasons to each other and “convince their neighbour”. If the majority do not have the correct answer, we typically vote again (after discussion) or do a similar/related question. Class size: 400
Growth & Goals Module
Please click here to see more information on Alison's project as the Chair in University Teaching at the University of Ottawa. In this project, we developed and evaluated a Growth & Goals module designed to better empower students in their own learning.
