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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 21 (2016) pp 159-161

Reactions of Hydroxy– and Alkoxy–Substituted Benzaldehydes with Sodium Iodide and Bleach in Methanol: A Guided–Inquiry Experiment for the Organic Chemistry Lab

Bruce A. Hathaway* and Karen M. Villermin

Department of Chemistry and Physics, LeTourneau University, PO Box 7001, Longview, TX, 75607,
Received June 27, 2016. Accepted July 17, 2016.

Published: 11 August 2016

Abstract. Vanillin and ethyl vanillin are iodinated ortho to the hydroxyl group, when treated with sodium iodide and bleach in methanol. Under similar conditions, 4–methoxybenzaldehyde and 3,4–dimethoxybenzaldehyde are converted into the corresponding methyl esters. This guided–inquiry organic chemistry laboratory experiment requires students to correctly interpret proton NMR and IR spectra to deduce whether their benzaldehyde iodinated or formed a methyl ester.

Key Words: Laboratories and Demonstrations; organic chemistry; electrophilic substitution; oxidation; iodination; oxidation; directed inquiry; NMR analysis

(*) Corresponding author. (E-mail:

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