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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 8 Issue 1 (2003) pp 28-32

Utilization of One-Dimensional Gradient NOE, HMQC, and COSY in Undergraduate Laboratories: Hydroboration–Oxidation of (1R)-(+)-a-Pinene Revisited

Brad Andersh

Department of Chemistry, Bradley University, Peoria, IL 61625,
Received October 29, 2002. Accepted November 18, 2002

Published online: 15 January 2003

Abstract. The identification of the product from the hydroboration–oxidation of (1R)-(+)-a-pinene provides an interesting example of the utilization of nuclear magnetic resonance spectroscopy (NMR) in undergraduate laboratories. In this experiment, one-dimensional gradient nuclear Overhauser enhancement spectroscopy and two-dimensional NMR spectroscopy (COSY and HMQC) are used to determine the stereochemistry of the product and to assign all proton NMR signals. The experiment is designed to enhance student understanding of three-dimensional structural determination and two-dimensional NMR spectroscopy.

Key Words:  Laboratories and Demonstrations; physical chemistry; NMR; 2-D NMR;

(*) Corresponding author. (E-mail:

Article in PDF format (310 KB) HTML format

Supporting Materials:

A handout for students, full-page spectra, and the 6-31G* geometry optimization output (588 KB zip file) 10.1333/s00897020652a. [updated 2/7/03]

Issue date: February 1, 2003

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