Updating Dimedone--The Humble Hero of the Organic Laboratory
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| Title: | Updating Dimedone--The Humble Hero of the Organic Laboratory |
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| Language: | English |
| Authors: | Alexander J. Wright, Dave Colclough, Hazel Harris, Stefano C. G. Biagini (ORCID |
| Source: | Journal of Chemical Education. 2023 100(8):3025-3028. |
| Availability: | 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: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc |
| Peer Reviewed: | Y |
| Page Count: | 4 |
| Publication Date: | 2023 |
| Document Type: | Journal Articles Reports - Descriptive |
| Education Level: | Higher Education Postsecondary Education |
| Descriptors: | Science Instruction, Science Laboratories, Organic Chemistry, Undergraduate Study, College Science, Spectroscopy, Hands on Science, Science Experiments, Laboratory Experiments |
| ISSN: | 0021-9584 1938-1328 |
| Abstract: | In this paper, we present a concise and technique-heavy route to the synthesis of dimedone for a second-year organic chemistry curriculum. Our preparation of dimedone guides students through a Michael addition followed by a Dieckmann cyclization, basic ester hydrolysis, and thermal decarboxylation, while allowing time for mechanistic discussion and analysis of the product. The wide variety of techniques covered led this to be a pedagogically diverse experiment. This task is thoroughly tested and suitable for a 6 hour laboratory class (with a 1 hour lunch break) or two 3 hour stand-alone sessions. |
| Abstractor: | As Provided |
| Entry Date: | 2024 |
| Accession Number: | EJ1444500 |
| Database: | ERIC |
| Abstract: | In this paper, we present a concise and technique-heavy route to the synthesis of dimedone for a second-year organic chemistry curriculum. Our preparation of dimedone guides students through a Michael addition followed by a Dieckmann cyclization, basic ester hydrolysis, and thermal decarboxylation, while allowing time for mechanistic discussion and analysis of the product. The wide variety of techniques covered led this to be a pedagogically diverse experiment. This task is thoroughly tested and suitable for a 6 hour laboratory class (with a 1 hour lunch break) or two 3 hour stand-alone sessions. |
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| ISSN: | 0021-9584 1938-1328 |
