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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 5 Issue 1 (2000) pp 20-23

Enhancement Spectroscopy (NOESY): Tools for Studying the Regioselective Bromination of 3-Bromoanisole

Brad Andersh

Department of Chemistry, Bradley University, Peoria, IL 61625

Published online: 1 February 2000

Abstract. The use of molecular modeling for predicting chemical reactivity has been highly successful in the industrial and academic research communities. For this reason, increased emphasis has been placed on molecular modeling in the undergraduate curriculum. In the described experiment, the bromination of 3- bromoanisole, students are encouraged to use molecular modeling software as a tool for predicting chemical reactivity. Besides introducing students to molecular modeling, this experiment incorporates the use of nontraditional, less hazardous reagents and solvents for electrophilic aromatic bromination reactions. Lastly, nuclear Overhauser enhancement spectroscopy (NOESY) is introduced as a tool for structural elucidation. Although there are a number of aspects to this experiment, two 3-hour laboratory periods are sufficient because the results from semiempirical (AM1) geometry optimizations, which are complete in seconds, were almost identical to the higher order, more time-intensive ab initio (3-21G*) calculations. In addition, the experimental time was greatly shortened by the discovery that catalytic HCl(aq) reduces the reaction time from 5 hours to 18 minutes.

Key Words:  Laboratories and Demonstrations; computers; organic chemistry; nuclear magnetic resonance; laboratory; NMR

(*) Corresponding author. (E-mail:})

Article in PDF format (112 KB ) HTML format

Supporting Materials:

Student handout (19 KB) 10.1007/s00897000353b

Spectra (223 KB)10.1007/s00897000353c

Output from AM1 calculations (18 KB) 10.1007/s00897000353d

(Note: DOI numbers listed on this page were corrected on 6/12/01 - [Editor])

Issue date: February 1, 2000

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