Use of a Biomimetic Catalyst in the Benzoin Condensation: A Bioorganic Laboratory Experiment

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 11 Issue 5 (2006) pp 327-332

Use of a Biomimetic Catalyst in the Benzoin Condensation: A Bioorganic Laboratory Experiment

Ana G. Neo, Jose Delgado, Carlos F. Marcos*

Laboratorio de Química Orgánica y Bioorgánica, LOBO, Departamento de Química Orgánica, Facultad de Veterinaria, Universidad de Extremadura, 10071 Cáceres, Spain, cfernan@unex.es
Received January 31, 2006. Accepted July 17, 2006.

Published online: 1 October 2006

Abstract. The traditional undergraduate organic laboratory “Benzoin condensation” is performed with the aid of 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride, a biomimetic catalyst modeled on vitamin B1. For comparison, the classical catalysts for this reaction, sodium cyanide and vitamin B1, are also used. The performance of the synthetic thiazolium catalyst is comparable, and in some terms superior, to cyanide and thiamin hydrochloride. The students are able to find suitable reaction conditions for each experiment, and draw conclusions about the differences and similarities between organic and biochemical reactions. The experiment serves to illustrate the transfer of knowledge between biochemistry and organic chemistry, which contributes to the advancement of both disciplines.

Key Words: Laboratories and Demonstrations; organic chemistry; synthesis

(*) Corresponding author. (E-mail: cfernan@unex.es)

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Supporting Materials:

Laboratory documentation containing a student handout and instructor notes is available in a Zip file (186 KB)