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McElveen, S. R., Gavardinas, K., Stamberger, J. A., and Mohan, R. S. The Discovery-Oriented Approach to Organic Chemistry. 1. Nitration of Unknown Organic Compounds: An Exercise in 1H NMR and 13NMR Spectroscopy for Sophomore Organic Laboratories. J. Chem. Educ. 1999, 75(4), 535-536.

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Article

Determination of the p/o-Isomer Product Ratios in Electrophilic Aromatic Nitration of Alkylbenzenes Using High Resolution 1H NMR Spectroscopy

1Department of Chemistry and Biochemistry, Hampton University, Hampton, VA 23668, U.S.A.


World Journal of Chemical Education. 2019, Vol. 7 No. 3, 216-224
DOI: 10.12691/wjce-7-3-5
Copyright © 2019 Science and Education Publishing

Cite this paper:
Michelle K. Waddell, Charles M. Bump, Edmund M. Ndip, Godson C. Nwokogu. Determination of the p/o-Isomer Product Ratios in Electrophilic Aromatic Nitration of Alkylbenzenes Using High Resolution 1H NMR Spectroscopy. World Journal of Chemical Education. 2019; 7(3):216-224. doi: 10.12691/wjce-7-3-5.

Correspondence to: Godson  C. Nwokogu, Department of Chemistry and Biochemistry, Hampton University, Hampton, VA 23668, U.S.A.. Email: godson.nwokogu@hamptonu.edu

Abstract

High resolution 1H NMR spectroscopy, an increasingly available instrumental method, is used in undergraduate organic laboratory practice as a simpler alternative to gas chromatographic method for the direct determination of the p/o ratios of the crude reaction product from the nitration of alkylbenzenes. The choice of isopropylbenzene as a substrate illustrates that steric effect can be significant in controlling regioselectivity in electrophilic aromatic substitution reactions.

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