KINETICS OF THE REACTION OF trans-3- METHYLTHIOACRYLOPHENONE WITH HYDROXIDE ION. DETECTION OF CARBANION INTERMEDIATE BY THE DIFFERENCE SPECTRUM.
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Reaction of trans-3-methylthioacrylophenone (MeSAcr) with hydroxide ion was followed spectrophotometric ally in aqueous solution. The reaction was found to be a typical series reaction : MeSAcr → benzoylacetaldehyde enolate → acetophenone. A carbanion intermediate, the enolate ion, was detected by the coincidence of difference spectra between the spectra in basic reaction solutions and in their acidified solutions with those between the spectra of benzoylacetaldehyde enolate and of the parent aldehyde. The first step of reaction in eq. (3) was kinetically first order in MeSAcr and first order in hydroxide ion. The second-order rate constants were obtained for MeSAcr-hydroxide ion combination reactions. The first-order rate coefficients for the second step of reaction in eq. (3) were obtained at the later stage of reaction where almost all MeSAcr was consumed. The rate coefficients are expressed as: k_<obs> = K₀ + k_<OH>⁻[OH⁻]. This is completely consistent with a mechanism for the hydrolysis of enolates of dicarbonyl compounds.
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