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Topic: Which hydrogen would be more acidic  (Read 1671 times)

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Offline limonade

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Which hydrogen would be more acidic
« on: August 12, 2013, 09:13:52 PM »
I am trying to do a condensation reaction and I have 3 phenyl propanal. If I treat this with sodium ethoxide and ethanol, which hydrogen would be more subject to deprotonation, the blue hydrogen closer to the carbonyl group which could have the negative charge stabilized by resonance on the oxygen, or the red benzyllic hydrogen, which could have the negative charge stabilized by the benzene ring? 

« Last Edit: August 12, 2013, 10:49:15 PM by limonade »
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Offline limonade

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Re: Which hydrogen would be more acidic
« Reply #1 on: August 12, 2013, 10:49:37 PM »
Sorry if the picture didn't come up. I hope it shows now. :)
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Offline Dan

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Re: Which hydrogen would be more acidic
« Reply #2 on: August 13, 2013, 02:56:25 AM »
Is a negative charge more stable on O or C?
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Offline limonade

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Re: Which hydrogen would be more acidic
« Reply #3 on: August 13, 2013, 09:16:18 AM »
Oxygen. Thank you.
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