Synthesis of Methyl Cyclopentanecarboxylate: A Laboratory Experience in Carbon Rearrangement.

CHEMICAL synthesis; CARBON analysis; ORGANIC chemistry education; CHEMICAL yield; NUCLEAR magnetic resonance spectroscopy; FAVORSKII rearrangement

We present a novel guided inquiry second semester organic chemistry laboratory rearrangement experiment. Students performed the Favorskii Rearrangement to obtain methyl cyclopentanecarboxylate in good yields. The students learned about the individual steps of the Favorskii mechanism and were required to propose a complete reaction mechanism and product structure. The students then confirmed the structure of the product by NMR and IR spectroscopy. This experiment provides students with experience in running organic chemistry reactions, structure determination, spectroscopy, general problem solving, and drawing rearrangement mechanisms. [ABSTRACT FROM AUTHOR]

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