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Topic: Which proton is the more acidic proton in the following diketone?  (Read 3544 times)

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Offline element41skater

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Which proton is the more acidic proton in the following diketone?
« on: January 19, 2011, 03:51:18 PM »
Which proton is the more acidic proton in the following diketone? (see link for picture)
I know it is the H between the 2 double bonded O's But why.  My feeling is that because the the oxygen is very electronegative it increase the acidity and because one oh the hydrogens is between to oxygens the effect is greater the the one only close to one of the oxygens. 

http://i207.photobucket.com/albums/bb289/element41skater/ChemistryOchem1.jpg
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Offline imrik

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Re: Which proton is the more acidic proton in the following diketone?
« Reply #1 on: January 20, 2011, 12:40:04 AM »
The best way to compare acidity is to compare the conjugate bases. Draw out the conjugate bases that result from deprotonation of the different hydrogens. The conjugate base that is more stable will correspond to the more acidic hydrogen. So which conjugate base is more stable? Hint:Think about resonance structures.
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