Acid-base chemistry is a foundational topic in undergraduate chemistry curricula, and student understanding of acids and bases has been studied extensively in introductory general chemistry courses. However, most existing research on acid-base chemistry in an organic chemistry context is related to acid strength and applications of the Lewis definition of acids and bases; there has been limited focus on identifying more nuanced misconceptions that organic chemistry students have about acid-base chemistry. To fill this gap, a survey for second-semester organic chemistry students was designed to probe the connections between acid-base chemistry and fundamental organic chemistry concepts, and its results are reported here. Building on existing research, molecular structure, hybridization, and important reaction mechanisms were identified as topics highly dependent on an accurate understanding of the Lewis definition. The misconceptions that students harbor about acids and bases in a second-semester organic chemistry course were analyzed using clustered quantitative, qualitative, and metacognitive methods. Prominent misconceptions include confusion of Brønsted acids and bases with electrophiles and nucleophiles when comparing elimination and nucleophilic substitution reactions, inaccurate applications of resonance to acid strength, and conflation of kinetics and thermodynamics in the aldol condensation. Between 15-30% of respondents demonstrated these misconceptions for each survey question, and these students were just as confident in their responses as their peers who answered correctly, suggesting inadequate metacognitive reflection on individual understanding. Future work will be focused on conducting interviews with second-semester organic chemistry students to further probe the justifications for these misconceptions. Additional surveys will also be designed for general chemistry and first-semester organic chemistry students to identify how misconceptions originate and propagate. The results from this and future surveys will provide insight into how undergraduate chemistry educators can revise their curricula to address these misconceptions and improve student learning outcomes.

Cluster analysis of second-semester organic chemistry students' misconceptions about acid-base chemistry

ACS Spring Meeting 2021

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