Synthesis of Methyl Cyclopentanecarboxylate: A Laboratory Experience in Carbon Rearrangement

• Alexandra Orchard ^[1] ; Roxanne V. Maniquis ^[1] ; Nicholas T. Salzameda ^[1]
  1. [1] California State University, United States
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 93, Nº 8, 2016, págs. 1460-1463
• Idioma: inglés
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• Resumen

  • 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.