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This laboratory experiment demonstrates the transformation of santonic acid into γ-metasantonin, highlighting student ingenuity in spectroscopic analysis.
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 γ-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).
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Testero et al. (2003) studied this question.
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