Why doesn't but-2-ene exhibit tautomerism like alkenols? By transfer of 1 hydrogen from terminal CH₃ to the middle carbon and forming a double bond between the two?
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2$\begingroup$ Getting a proton off an oxygen is easy peasy. Getting it off a carbon is not usually quite so easy. $\endgroup$– orthocresolApr 3, 2019 at 9:16
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1 Answer
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In order for tautomerism to occur, the enol must be deprotonated, so as to allow the negative charge to come down, kick the pi bond of the C=C bond, which will bond to a proton. Hydrogen atoms on oxygen are much more acidic than hydrogens on carbons because of the electronegativity differences between O and H. Thus, the deprotonation does not happen in alkenes.