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Topic: peracetic acid polarization  (Read 2075 times)

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Offline Koemelk

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peracetic acid polarization
« on: April 21, 2014, 09:47:37 AM »
Hey! Normally I'm more of a searcher than asker, but this really hasn't been asked:
Can someone tell me how a peracetic acid is polarized? I can't seem to find this anywhere, and I'm disturbed by the fact if you should consider polarization by EN difference, or by PCMO partial charges.
http://upload.wikimedia.org/wikipedia/commons/a/a8/Peracetic_acid_structure.png
In my coursebook they seem to think that the most right Oxygen has a partial positive charge (so the oxygen rcoo-Oh)
why?




The reaction I'm talking about is the following:
http://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/Images2/epoxide1.gif

Offline Hunter2

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Re: peracetic acid polarization
« Reply #1 on: April 21, 2014, 11:32:49 AM »
Here you have to consider the week O-O bond. The positive polarisation of H will induct over the first oxygen. It is electrophil. In the epoxy-reaction the doublebond of the alkene will attract the slighltly positve OH instead of an H+ what would happen with an normal acid.  After forming the carbo cation. The negative acetate attracts the hydrogen and the ring will be closed.

Offline zsinger

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Re: peracetic acid polarization
« Reply #2 on: April 21, 2014, 01:05:17 PM »
Hint:
As stated above, what makes a good "oxidizer"?  (Hint: Think bond strength).  Do you think Oxygen forms a stronger bond to itself or another element?
                      -Z
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