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

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Bibliographic Details
Published in:Journal of chemical education 2016-08, Vol.93 (8), p.1460-1463
Main Authors: Orchard, Alexandra, Maniquis, Roxanne V, Salzameda, Nicholas T
Format: Article
Language:English
Subjects:
Active Learning
College Science
Infrared spectroscopy
Inquiry
Laboratory Experiments
NMR
Nuclear magnetic resonance
Organic Chemistry
Problem Solving
Reaction mechanisms
Science education
Science Experiments
Science Instruction
Science Laboratories
Spectroscopy
Students
Undergraduate Students
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Summary: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.
ISSN:0021-9584
1938-1328
DOI:10.1021/acs.jchemed.5b00588