An Undergraduate Computational Chemistry Experiment: Investigation of the E2 Elimination Reaction of 2-Bromopropane to Propene

Monsurat M. Lawal¹ and Tugba G Kucukkal^1,

¹School of Science, Technology, Accessibility, Mathematics and Public Health, Gallaudet University, Washington, DC 20002, USA

Cite this paper:
Monsurat M. Lawal and Tugba G Kucukkal. An Undergraduate Computational Chemistry Experiment: Investigation of the E2 Elimination Reaction of 2-Bromopropane to Propene. World Journal of Chemical Education. 2024; 12(1):13-18. doi: 10.12691/wjce-12-1-3

Abstract

This paper presents an undergraduate computational chemistry lab experiment of the E2 elimination reaction of 2-bromopropane to form propene. Utilizing the Hartree-Fock (HF) and Density Functional Theory (DFT) methods within the computational frameworks of Avogadro and ORCA, the experiment offers a comprehensive insight into the reaction mechanism, activation energy, and electronic structure changes associated with the reaction. The experiment was structured to enhance students' understanding of key concepts in quantum chemistry and organic chemistry, including molecular orbitals, electron density, and reaction kinetics. By calculating and analyzing the activation energy and reaction pathways, students will gain a deepened understanding of the transition states and the energy profiles of the E2 elimination process. The experiment effectively demonstrates theoretical principles applications to practical scenarios, correlating computational findings with experimental data when available, thereby bridging the gap between theory and practice. It also fosters the development of critical thinking and problem-solving skills through hands-on experience with computational tools and data analysis. This approach not only elucidates the fundamental principles of the E2 elimination reaction but also highlights the versatility and significance of computational methods in modern chemical research and education.

Keywords:
E2 elimination reaction computational chemistry experiment undergraduate experiment organic chemistry

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References:

[1]	Leach, A., Computational Chemistry. A Practical Guide for Applying Techniques to Real World Problems, Wiley Interscience John Wiley & Sons, New York, 2001, 19-21.
[2]	Leach, A., Computational Chemistry. A Practical Guide for Applying Techniques to Real World Problems, Wiley Interscience John Wiley & Sons, New York, 2001, 42-44.
[3]	Went, C., “Elimination,” Ionic Organic Mechanisms, 123-141. 1986.
[4]	Hanwell, M.D. et al. Avogadro: an advanced semantic chemical editor, visualization, and analysis platform. J. Cheminformatics 4, 17. 2012.
[5]	Neese, F., “Software update: The ORCA program system—Version 5.0.” Wiley Interdisciplinary Reviews: Comput. Mol. Sci. 12(5), e1606. 2022.
[6]	Snyder, H.D. and Kucukkal, T.G., “Computational Chemistry Activities with Avogadro and ORCA” J. Chem. Educ. 98(4). 1335-1341. 2021.
[7]	Gill, P.M., Johnson, B.G., Pople, J.A., and Frisch, M.J., “The performance of the Becke—Lee—Yang—Parr (B—LYP) density functional theory with various basis sets” Chem. Phys. Lett. 197(4-5), 499-505. 1992.
[8]	Weigend, F., “Accurate Coulomb-fitting basis sets for H to Rn” Phys. Chem. Chem. Phys. 8(9), 1057-1065. 2006.
[9]	Kruse, H., Goerigk, L. and Grimme, S., “Why the standard B3LYP/6-31G* model chemistry should not be used in DFT calculations of molecular thermochemistry: understanding and correcting the problem” J. Org. Chem. 77(23), 0824-10834. 2012.
[10]	Lawal, M.M. et al. “Mechanistic investigation of the uncatalyzed esterification reaction of acetic acid and acid halides with methanol: a DFT study” J. Mol. Model. 22, 1-12. 2016.
[11]	Lide, D.R., CRC Handbook of Chemistry and Physics, CRC Press, 2004, 85.
[12]	Revell, L.E. and Bryce, E.W., “Why are some reactions slower at higher temperatures?” J. Chem. Edu. 90(8), 1024-1027. 2013.
[13]	Lawal, M.M. et al. “DFT study of the acid‐catalyzed esterification reaction mechanism of methanol with carboxylic acid and its halide derivatives” Int. J. Quantum Chem. 118(4), e25497. 2018.
[14]	Takano, Y. and Houk, K.N. “Benchmarking the conductor-like polarizable continuum model (CPCM) for aqueous solvation free energies of neutral and ionic organic molecules” J. Chem. Theory Comput. 1(1), 70-77. 2005.