Kinetics of the Decarboxylation of Acetoacetic acid
RW Hay and MA Bond
Australian Journal of Chemistry
20(9) 1823 - 1828
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