Journal of Organic Chemistry p. 775 - 779 (1982)
Update date:2022-08-11
Topics:
Allen, Annette D.
Chiang, Yvonne
Kresge, A. Jerry
Tidwell, Thomas T.
The rates of hydration in aqueous sulfuric acid of 1-butyne, 2-butyne, 1-hexyne, 1-cyclopropylacetylene, and 1-butene are reported, together with rates in D2SO4 for the alkynes plus 3-hexyne.All of the compounds are proposed to react through the AdE2 mechanism of rate-limiting protonation on carbon.A general correlation of logkH+(alkyne)/log kH+(alkene) is observed, whose slope of 1.25 is a quantitative measure of the greater sensitivity to substituent effects of alkynes compared to alkenes in protonation.
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