0
$\begingroup$

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?

$\endgroup$
1
  • 2
    $\begingroup$ Getting a proton off an oxygen is easy peasy. Getting it off a carbon is not usually quite so easy. $\endgroup$ Apr 3, 2019 at 9:16

1 Answer 1

1
$\begingroup$

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.

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge that you have read and understand our privacy policy and code of conduct.

Not the answer you're looking for? Browse other questions tagged or ask your own question.