Case Comparisons on the Basicity of Organic Nitrogen Compounds to Develop the Concepts of 'inductive effect' and 'mesomeric effect' in the Teaching Laboratory

Johannes Ruprecht¹ and Michael Schween^1,

¹Fachbereich Chemie, Philipps-Universität Marburg, Germany

Cite this paper

Johannes Ruprecht and Michael Schween. Case Comparisons on the Basicity of Organic Nitrogen Compounds to Develop the Concepts of 'inductive effect' and 'mesomeric effect' in the Teaching Laboratory. World Journal of Chemical Education. 2023; 11(3):25-30. doi: 10.12691/WJCE-11-3-2

Abstract

Inductive and resonance effects play an important role in understanding a variety of organic chemical reactions and their mechanisms. Most reactions are kinetic-controlled reactions, in which the effects take effect via the stabilization of reactive intermediates over shorter or longer reaction times. - To avoid this mental "detour", we have developed new learning opportunities on equilibrium reactions of organic bases with water for high school teacher education, with which inductive and resonance effects can be quickly worked out using conductivity and pH measurements. The learning opportunity has already been successfully tested in teacher education in Marburg.

Keywords

Basicity of Organic Compounds, Contrasting Cases, Inductive Effects, Resonance Effects, Teaching Lab

Copyright

This work is licensed under a Creative Commons Attribution 4.0 International License. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/

References

[1]	Hazardous Substances Data Bank (HSDB) : 78 - PubChem (nih.gov), last accessed on 1.2.2023.
[2]	Kaupmees, K., Trummal, A. and Leitoa, I. “Basicities of Strong Bases in Water: A Computational Study”, Croat. Chem. Acta, Volume 87, issue 4, 385–395, 2014.
[3]	R. Williams, Bordwell pKa Table, URL: pka-compilation-williams.pdf (organicchemistrydata.org), last accessed on 31.1.2023.
[4]	Ripin, D. H., Evans, D.A., pka´s of Nitrogen Acids, evans_pKa_table.pdf (pitt.edu), last accessed on 1.2.2023.
[5]	Schwartz, D . L., Chase, C. C., Oppezzo, M. A. and Chin, D. B., “Practicing versus inventing with contrasting cases: The effects of telling first on learning and transfer”, J. Educ. Psychol., Volume 103, 759–775, 2011.
[6]	Trabert, A., Schmitt, C. and Schween, M., “Chapter 15. Building Bridges Between Tasks and Flasks - Design of a Coherent Experiment-supported Learning Environment for Deep Reasoning in Organic Chemistry”, in: Graulich, N., Shultz, G,. “Student Reasoning in Organic Chemistry”, The Royal Society of Chemistry, 248-265, 2022.
[7]	Goodwin, W. M., “Structural formulas and explanation in organic chemistry”, Found. Chem., Volume 10, 117–127, 2008.
[8]	Graulich, N., Schween, M., “Concept-Oriented Task Design: Making Purposeful Case Comparisons in Organic Chemistry”, Journal of Chemical Education, Volume 95, Issue 3, 376-383, 2018.
[9]	Trabert, A., Eckert, F. and Schween, M., “Kohlenstoff-Kohlenstoff-Bindungen knüpfen lernen – ein Modellexperiment zum konzeptbasierten Problemlösen“, CHEMKON, Volume 23, Issue 4, 163–169, 2016.