Researches on acetylenic compounds. Part LXVI. Base catalysed interconversions between pent-2-ynoic, penta-2, 3-dienoic, and pent-3-ynoic acids—a mechanistic …
RJ Bushby, GH Whitham
Index: Bushby,R.J.; Whitham,G.H. Journal of the Chemical Society [Section] B: Physical Organic, 1969 , p. 67 - 73
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Citation Number: 8
Abstract
The sodium salts of pent-2-ynoic (I), penta-2, 3-dienoic (II), and pent-3-ynoic (III) acids are interconverted on heating in aqueous sodium hydroxide. The reaction was followed by gc analysis of the methyl esters after methylation of the acid mixtures with diazomethane at– 70°. Rate and equilibrium constants for the individual steps were obtained, allowance being made for a competing hydration reaction. Solvent isotope effects k (D2O)/k (H2O) for the ...
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