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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: limonade on August 12, 2013, 09:13:52 PM

Title: Which hydrogen would be more acidic
Post by: limonade 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? 

Title: Re: Which hydrogen would be more acidic
Post by: limonade on August 12, 2013, 10:49:37 PM

Sorry if the picture didn't come up. I hope it shows now. :)

Title: Re: Which hydrogen would be more acidic
Post by: Dan on August 13, 2013, 02:56:25 AM

Is a negative charge more stable on O or C?

Title: Re: Which hydrogen would be more acidic
Post by: limonade on August 13, 2013, 09:16:18 AM

Oxygen. Thank you.