3
$\begingroup$

Why is the enol content of acetylacetone higher than that of acetoacetic ester? Hydrogen bonding stabilisation is present in enol form of both of them. I cannot figure out which factor makes one predominate over another.

$\endgroup$
4
  • 2
    $\begingroup$ Since the stabilisation by hydrogen bonding is about the same, we might as well just take it away. Try comparing acetone and ethyl acetate, which is more prone to enolisation? $\endgroup$ – orthocresol Nov 9 '16 at 13:22
  • $\begingroup$ @orthocresol Acetone is more prone to enolisation, but same problem persists, why is it more prone? $\endgroup$ – user340743 Nov 10 '16 at 14:00
  • 4
    $\begingroup$ To enolise a carbonyl compound, you need to deprotonate the adjacent oxygen and push electrons into the C=O π* orbital, right? (And then you reprotonate on oxygen, but that doesn't make a difference here.) Well, in an ester, there's already one oxygen pushing electrons into that C=O π*. That makes it less interested in enolisation. $\endgroup$ – orthocresol Nov 11 '16 at 0:47
  • $\begingroup$ @orthocresol Got that! Accept my word of thanks. $\endgroup$ – user340743 Nov 11 '16 at 8:50

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.