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The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 20 (2015) pp 265-267

An Improved Resolution of (±)-1-Phenylethylamine

Daniel D. Clark,* Peter D. McFadden, and Emily S. Wilson

Department of Chemistry, Mathematics, and Physics, Clarion University of Pennsylvania, 840 Wood Street, Clarion, PA 16214,
Received August 26, 2015. Accepted October 6, 2015.

Published: 9 October 2015

Abstract. Stereochemistry and polarimetry are often introduced in organic chemistry laboratory with the resolution of (±)-1-phenylethylamine using (+)-tartaric acid as the resolving agent. However, there are significant drawbacks to the commonly used experimental procedure. Isolating the resolved (–)-1-phenylethylamine from solution is problematic as it is viscous, reacts with the atmospheric carbon dioxide, and stinks. Furthermore, the use of a full equivalent of (+)-tartaric acid resolving agent requires a large volume of solvent. We have developed two practical improvements to this experiment: (1) By keeping the resolved amine in solution and measuring its concentration with refractometry, the isolation of the problematic neat amine is avoided; and (2) By decreasing the amount of resolving agent, the resolution can be accomplished using appreciably less solvent and generating less chemical waste, thus making the experiment greener.

Key Words: Laboratories and Demonstrations; organic chemistry; stereochemistry; optical resolution; experiment; optical purity

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