01675nam a22002777a 450000500170000000800410001702200140005803700190007208200100009110000270010124500870012826000490021530000190026449000510028350500630033452006210039765000150101865000760103365000340110965000430114365000330118685600620121994200080128195200910128999900170138020231116101256.0231020b           ||||| |||| 00| 0 eng d  a0021-9584  bRIEBPL Library  a540.7  aAlexander J  et al ...  a Updating Dimedone─The Humble Hero of the Organic Laboratoryb (Journal Article)  aUSAb:American Chemical SocietycAugust 2023  a 3025-3028  P.  aAmerican Chemical Society, Volume 100, Issue 8  a***______{For Hard Copy, Please visit Library.}________***  aAbstract
 
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.

  aSynthesis   aEquilibrium Reactions NMR Spectroscopy Hands-On Learning/Manipulatives   aOrganic Chemistry Laboratory   aInstruction Second-Year Undergraduate   aUpper-Division Undergraduate  uhttps://pubs.acs.org/doi/epdf/10.1021/acs.jchemed.3c00069  cPER  00104070aRIEBPLbRIEBPLd2023-11-16l0o540.7r2023-11-16 00:00:00w2023-11-16yPER  c44881d44880