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Assigning the NMR Spectrum of Glycidol: An Advanced Organic Chemistry Exercise

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Eric Helms , Nicholas Arpaia and Melissa Widener

Department of Chemistry, State University of New York College at Geneseo, Geneseo, NY, 14454

J. Chem. Educ., 2007, 84 (8), p 1328

DOI: 10.1021/ed084p1328

Publication Date (Web): August 1, 2007

Section:

History, Education, and Documentation

Abstract

This exercise combines conformational analysis and 1-D and 2-D NMR spectroscopy to correctly assign the proton and carbon NMR spectra of 2,3-epoxy-1-propanol (glycidol). In the process, students learn how to read DEPT-135, HETCOR, and COSY spectra. One set of diastereotopic protons is assigned using dihedral angles and the Karplus relationship. The assignment of the other set of diastereotopic protons requires that conformational modeling be done to complete the assignment of protons to signals.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Feature):

Molecular Modeling Exercises and Experiments

Keywords (Pedagogy):

Computer-Based Learning

Keywords (Subject):

Conformational Analysis

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