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The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 19 (2014) pp 330-332

Photolysis of a Cyclic Carbonate Ester and a Cyclic Sulfite Ester: Radical Intermediates and Ionic Intermediates in an Advanced Laboratory Experiment

Benny E. Arney, Jr.*, Jacob Perry, Nathan Thompson and Rick C. White*

Department of Chemistry, Sam Houston State University, Huntsville, TX 77341,
Received August 5, 2014. September 25, 20145

Published: 20 November 2014

Abstract. The experiment in this paper addresses mechanistic approaches to chemical reactions involved in an undergraduate advanced laboratory exercise. In this experiment, students will prepare two structurally similar molecules, subject these to irradiation in a polar aprotic solvent and a polar protic solvent, and analyze the mixtures by Nuclear Magnetic Resonance spectroscopy. In this experiment, students can observe an ionic intermediate through observation of a photochemical solvolysis product with one compound, but not with the other substrate.

Key Words: In the Classroom; organic chemistry; photochemistry; photosolvolysis

(*) Corresponding author. (E-mail:

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