Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science

Kinetics of the Decarboxylation of Acetoacetic acid

RW Hay and MA Bond

Australian Journal of Chemistry 20(9) 1823 - 1828
Published: 1967


The decarboxylation of acetoacetic acid CH3COCH2CO2H → CH3COCH3+CO2 and its anion have been studied in aqueous solution over a range of temperature. Although the acid decomposes approximately 50 times faster than the anion at 37°, the activation energy of the acid (23.7 kcal mole-1) is comparable with that of the anion (22.9 kcal mole-1) and the large difference in reactivity is due to an entropy effect. The significance of these results is discussed and a comparison made with other β-keto acid decarboxylations.

© CSIRO 1967

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