Making Sense of Reaction Mechanisms: Developing Assessment Tools for the Learning of Organic Chemistry

Reasoning about underlying mechanisms of observed chemical phenomena lies at the core of scientific practices.¹ To prepare for work as scientists and engineers, students should engage in scientific and engineering practices such as developing and using models to predict and explain phenomena, and constructing arguments from evidence.^1-5 One way to engage students in these practices is through three-dimensional (3D) learning; 3D assessments require students to integrate chemistry core ideas with scientific practices and crosscutting concepts (for example, see figure from ref. 5).^6,7 Written constructed response assessment items that ask students to explain, make a prediction, and provide their reasoning offer the strongest evidence of 3D learning.⁷ With large enrollment courses such as general and organic chemistry, its use is hindered by effort required to evaluate writing and provide feedback to students in a timely manner. However, I have demonstrated in my Ph.D. work that machine learning technologies can automate the scoring of these assessments.⁸ This research area will further support student learning of chemical phenomena through machine learning-based adaptive formative assessment of 3D learning tasks.

(1) National Research Council. Developing Assessments for the Next Generation Science Standards. The National Academies Press: Washington, DC, 2014. 

(2) Stowe, R. L.; Scharlott, L. J.; Ralph, V. R.; Becker, N. M.; Cooper, M. M. You Are What You Assess: The Case for Emphasizing Chemistry on Chemistry Assessments. J. Chem. Educ. 2021, 98 (8), 2490-2495. 

(3) Stowe, R. L.; Cooper, M. M. Assessment in Chemistry Education. Isr. J. Chem. 2019, 59 (6-7), 598- 607. 

(4) Cooper, M. M.; Stowe, R. L. Chemistry Education Research—From Personal Empiricism to Evidence, Theory, and Informed Practice. Chem. Rev. 2018, 118 (12), 6053-6087. 

(5) Stowe, R. L.; Cooper, M. M. Practicing What We Preach: Assessing “Critical Thinking” in Organic Chemistry. J. Chem. Educ. 2017, 94 (12), 1852-1859. 

(6) Underwood, S. M.; Posey, L. A.; Herrington, D. G.; Carmel, J. H.; Cooper, M. M. Adapting Assessment Tasks To Support Three-Dimensional Learning. J. Chem. Educ. 2018, 95 (2), 207-217. 

(7) Laverty, J. T.; Underwood, S. M.; Matz, R. L.; Posey, L. A.; Carmel, J. H.; Caballero, M. D.; FataHartley, C. L.; Ebert-May, D.; Jardeleza, S. E.; Cooper, M. M. Characterizing College Science Assessments: The Three-Dimensional Learning Assessment Protocol. PLOS ONE 2016, 11 (9), e0162333.

(8) Yik, B. J.; Dood, A. J.; Cruz-Ramírez de Arellano, D.; Fields, K. B.; Raker, J. R. Development of a machine learning-based tool to evaluate correct Lewis acid–base model use in written responses to open-ended formative assessment items. Chem. Educ. Res. Pract. 2021, 22 (4), 866-885.