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Article << Previous     |     Next >>   Contents Vol 20(9)

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.

Full text doi:10.1071/CH9671823

© CSIRO 1967

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