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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 7 Issue 3 (2002) pp 155-158

A New Laboratory Experiment Based on a Chemical Transformation of Santonin: Synthesis of Santonic Acid

Silvina C. Pellegrinet, María I. Colombo, Sebastián A. Testero, Manuel González Sierra, and Edmundo A. Rúveda*

Instituto de Química Orgánica y de Síntesis (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Casilla de Correo 991, 2000 Rosario, Argentina
Received February 13, 2002. Accepted March 22, 2002

Published online: 10 May 2002

Abstract. In this paper we describe a new comprehensive laboratory experiment based on a chemical transformation of santonin. The experiment is designed as a puzzle-solving exercise for advanced undergraduate organic chemistry courses and consists of the structure elucidation of santonic acid, the product obtained by the action of strong alkalis on santonin. An enquiry-based approach helps the students achieve this goal by combining their knowledge of organic chemistry and spectroscopy together with mechanistic thinking.

Key Words:  Laboratories and Demonstrations; organic chemistry; synthesis

(*) Corresponding author. (E-mail: eruveda@fbioyf.unr.edu.ar)

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Issue date: June 7, 2002

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