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Updating dimedone - The humble hero of the organic laboratory

Wright, AlexanderJ., Colclough, Dave, Harris, Hazel, Biagini, Stefano C. G. (2023) Updating dimedone - The humble hero of the organic laboratory. Journal of Chemical Education, 100 (8). pp. 3025-3028. ISSN 1938-1328. (doi:10.1021/acs.jchemed.3c00069) (KAR id:102391)


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.

Item Type: Article
DOI/Identification number: 10.1021/acs.jchemed.3c00069
Uncontrolled keywords: Synthesis, equilibrium, reactions, NMR spectroscopy, hands-on learning/manipulatives, organic chemistry, laboratory instruction, second-Year undergraduate, upper-division undergraduate
Subjects: Q Science
Divisions: Divisions > Division of Natural Sciences > Chemistry and Forensics
Funders: University of Kent (
SWORD Depositor: JISC Publications Router
Depositing User: JISC Publications Router
Date Deposited: 20 Oct 2023 13:22 UTC
Last Modified: 23 Oct 2023 14:24 UTC
Resource URI: (The current URI for this page, for reference purposes)

University of Kent Author Information

Biagini, Stefano C. G..

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