# What is the major hydrolysis product of 2,2,2-trifluoroethyl 2-acetamido-3-phenylprop-2-enoate?

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

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?

• That's a not a hydrolysis product. Are you just asking for the "hydrolysis product" because of the reaction conditions? – Zhe Dec 1 '16 at 14:43
• @Zhe which one is not hydrolysis product . The one which I thought or the other one – user38134 Dec 1 '16 at 14:48
• The other one. How is that hydrolysis? – Ivan Neretin Dec 1 '16 at 14:53
• 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. – Ivan Neretin Dec 1 '16 at 14:55
• @IvanNeretin why it is hard to hydrolyse – user38134 Dec 1 '16 at 15:06

## 1 Answer

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.

• How can we know which reaction can produce major product – user38134 Dec 1 '16 at 15:05
• Does the second reaction is also hydrolysis – user38134 Dec 1 '16 at 15:07
• @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. – Klaus-Dieter Warzecha Dec 1 '16 at 15:16
• That reaction is not hydrolysis, it's a transesterification. – Variax Dec 1 '16 at 15:42
• @Variax Yes, just as I wrote in my answer ;) – Klaus-Dieter Warzecha Dec 1 '16 at 15:54