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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 17 (2012) pp 094-097
DOI 10.1007/s00897122423a

Nitration of p-Anisaldehyde: The Effect of Temperature on Product Distribution

Kwesi Amoa* and Dereck Skeete

Medgar Evers College/City University of New York; Physical Environmental, and Computer Sciences Department, Brooklyn, New York 11225, kamoa@mec.cuny.edu
Received January 28, 2012. Accepted May 16,2012.

Published: 8 June 2012

Abstract. In any organic chemistry class, students are faced with learning functional group transformation where the emphasis is placed on the effect of temperature on various chemical reactions. However, in a laboratory setting students rarely receive any practical hands-on experience in observing this effect. In this laboratory experiment, students nitrate p-anisaldehyde at –15 to –8 ^°C and from 25 to 40 ^°C using a nitric acid/sulfuric acid solution. Gas Chromatography/Mass Spectroscopy (GC/MS) analysis of the reaction mixture at a lower temperature range revealed a single compound, 4-methoxy-3-nitrobenzaldehyde (1), while GC/MS analysis of the reaction mixture at the higher temperature range revealed 4-methoxy-3-nitrobenzaldehyde (1) as the major product and three additional by-products – 2-nitroanisole (2), 4-methoxy-3,5-dinitrobenzaldehyde (3), and 2,4-dinitroanisole (4). This laboratory experiment can be used as a template for complementing undergraduate laboratory experiments that exclude the qualitative or quantitative effect of temperature on product distribution.

Key Words: Laboratories and Demonstrations; organic chemistry; aromatic compounds; electrophilic substitution; hands-on learning; inquiry-based laboratory instruction; gas chromatography; mass spectrometry; second-year undergraduate

(*) Corresponding author. (E-mail: kamoa@mec.cuny.edu)

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