Undergraduate Inquiry Activities Using Organic Chemistry Laboratory Instrumentation

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 14 Issue 6 (2009) pp 250-254

Undergraduate Inquiry Activities Using Organic Chemistry Laboratory Instrumentation

James Schreck*, Alden Bailey, Aaron Klein, Josh Gunter, Ashley Campbell and David Pringle

School of Chemistry & Biochemistry, University of Northern Colorado, Greeley, CO 80639, James.Schreck@unco.edu
Received January 26, 2009. Accepted February 20, 2009

Published online: 3 November 2009

Abstract. Three inquiry activities for undergraduate organic chemistry laboratory work are described. The first involves the reduction of acetophenone with separation of stereoisomers by gas chromatography using a chiral column. Students discover that a racemic mixture is obtained, supporting the known mechanism. IR and NMR spectroscopy are used to study the completeness of the reduction. In the second investigation, involving the Friedel–Crafts reaction of benzene and ethyl iodide, gas chromatography/mass spectrometry are used to identify various products. The rearrangement of one product under reaction conditions can be deduced by students. The third activity is the carbocation rearrangement of an S_N1 reaction of a secondary alcohol. Students use ¹H NMR to investigate the rearrangement and determine the extent of the rearrangement.

Key Words: Laboratories and Demonstrations; organic chemistry; spectroscopy

(*) Corresponding author. (E-mail: James.Schreck@unco.edu)

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