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The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 8 Issue 6 (2003) pp 364-366

The Transformation of Santonic Acid into g-Metasantonin: A Challenging Chemical Puzzle for Advanced Undergraduate Organic Chemistry Students

Sebastián A. Testero, María I. Colombo, and Edmundo A. Rúveda*

Instituto de Química Orgánica y de Síntesis (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Suipacha 531, 2000 Rosario, Argentina,
Received July 21, 2003. Accepted September 4, 2003.

Published online: 12 October 2003

Abstract. The ingenuity of advanced undergraduate organic chemistry students in structure elucidation by combining mechanistic thinking with spectroscopic data and molecular modeling calculations is challenged by this simple experiment: the transformation of santonic acid (3) into g-metasantonin (4) by the action of sulfuric acid. An inquiry-based approach helps the students to achieve this goal. This is the third of a series of laboratories related to the fascinating chemistry of the sesquiterpene santonin (1).

Key Words:  Laboratories and Demonstrations; organic chemistry; computational chemistry; synthesis

(*) Corresponding author. (E-mail:

Article in PDF format (226 KB) HTML format

Supporting Materials:


Supporting Materials:

A student prelaboratory assignment and the experimental procedure are available in a Zip file (97 KB) (10.1007/s00897030736a)


Issue date: December 1, 2003

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