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ERIC Number: EJ1110412
Record Type: Journal
Publication Date: 2016-Aug
Pages: 4
Abstractor: As Provided
ISSN: ISSN-0021-9584
Synthesis of Methyl Cyclopentanecarboxylate: A Laboratory Experience in Carbon Rearrangement
Orchard, Alexandra; Maniquis, Roxanne V.; Salzameda, Nicholas T.
Journal of Chemical Education, v93 n8 p1460-1463 Aug 2016
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.
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A