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Author: Subject: Concerning Phenyl Acetate
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[*] posted on 1-4-2019 at 19:25
Concerning Phenyl Acetate


Would some one explain why the conjugate base phenylacetate results into phenol and acetic acid when hydrolized instead of into Phenylacetic acid. If Phenyl Acetate is its conjugate base, then should not it form Phenylacetic acid?
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[*] posted on 1-4-2019 at 19:36


Phenyl acetate is an ester. Hydrolysis will break it apart into the alcohol and the acid that it was formed from: in this case, phenol and acetic acid.

Phenylacetic acid is actually quite a different species. It is acetic acid with a benzene ring substituted for one of the hydrogens.

In other words, the orientation of the acetic acid is different. In phenylacetate, the acid group is in the middle of the molecule. In phenylacetic acid the acid group is terminal.

https://en.wikipedia.org/wiki/Phenyl_acetate
https://en.wikipedia.org/wiki/Phenylacetic_acid
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[*] posted on 1-4-2019 at 19:39


That explains why the hydrolysis of benzyl cyanide is used to form Phenylacetic acid.
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[*] posted on 1-4-2019 at 19:48


You're confusing phenyl acetate (which is an ester) with phenylacetate (the conjugate base of phenylacetic acid). The space is important.



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[*] posted on 1-4-2019 at 20:13


I noticed the difference between the two after. I should have corrected it. If I err, then blame Wikipedia.
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