In the below reaction we have to find the major hydrolysis product of 2,2,2-trifluoroethyl 2-acetamido-3-phenylprop-2-enoate.

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My doubt is why the major hydrolysis is not when $\ce{OH-}$ at the $\ce{C}$ of $\ce{CF3}$ as it is more electropostive. However the major product is given by the following reaction, why?

enter image description here

  • 1
    $\begingroup$ That's a not a hydrolysis product. Are you just asking for the "hydrolysis product" because of the reaction conditions? $\endgroup$
    – Zhe
    Commented Dec 1, 2016 at 14:43
  • $\begingroup$ @Zhe which one is not hydrolysis product . The one which I thought or the other one $\endgroup$
    – user38134
    Commented Dec 1, 2016 at 14:48
  • $\begingroup$ The other one. How is that hydrolysis? $\endgroup$ Commented Dec 1, 2016 at 14:53
  • 2
    $\begingroup$ Also, C-F bonds are notoriously hard to hydrolyze. You should have supposed that hydrolysis would simply break the ester, that would be at least logical. $\endgroup$ Commented Dec 1, 2016 at 14:55
  • $\begingroup$ @IvanNeretin why it is hard to hydrolyse $\endgroup$
    – user38134
    Commented Dec 1, 2016 at 15:06

1 Answer 1


Plain hydrolysis would just replace trifluorexthoxide with hydroxide.

But you might want to consider that your staring material in equilibrium with another tautomer:


Deprotonation of the $\ce{OH}$ in the right structure, followed by an intramolecular reaction (transesterification/lactonization) in which $\ce{CF3CH2O-}$ is kicked out should give rise to an oxazolone.

  • $\begingroup$ How can we know which reaction can produce major product $\endgroup$
    – user38134
    Commented Dec 1, 2016 at 15:05
  • $\begingroup$ Does the second reaction is also hydrolysis $\endgroup$
    – user38134
    Commented Dec 1, 2016 at 15:07
  • $\begingroup$ @J.Doe Hydrolysis is an extremely broad term. I'd rather call this a cyclization, which is still broad but describes the outcome of the reaction much better. On a second look, this looks a bit an intramolecular variant of the Erlenmeyer-Plöchl reaction. $\endgroup$ Commented Dec 1, 2016 at 15:16
  • $\begingroup$ That reaction is not hydrolysis, it's a transesterification. $\endgroup$
    – Variax
    Commented Dec 1, 2016 at 15:42
  • $\begingroup$ @Variax Yes, just as I wrote in my answer ;) $\endgroup$ Commented Dec 1, 2016 at 15:54

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