DAT Destroyer Ochem Question?

[nayryecal]

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Hi!
So Im looking at number 31 on the 2013 dat destroyer and Im wondering why the carboxylic acid hydrogen would be more acidic than the hydrogen between the same carboxylic acid and ketone? Wouldn't it have more resonance structures?

Thanks!

 

[LazyP]

i too would like to know more about the reasoning and exceptions behind the "most acidic hydrogen" concept but so far its because the negative charge would be on O vs C when u take the H away and O is more stabilized due to CARDIO, thus more acidic hydrogen. I really want to confirm this with others but it makes sense.

 

[nayryecal]

i too would like to know more about the reasoning and exceptions behind the "most acidic hydrogen" concept but so far its because the negative charge would be on O vs C when u take the H away and O is more stabilized due to CARDIO, thus more acidic hydrogen. I really want to confirm this with others but it makes sense.

Yes! I think youre right that does make sense 👍

 

[Koalafied]

Hi!
So Im looking at number 31 on the 2013 dat destroyer and Im wondering why the carboxylic acid hydrogen would be more acidic than the hydrogen between the same carboxylic acid and ketone? Wouldn't it have more resonance structures?

Thanks!

Understand the pKa trends. It's all about how readily the protons dissociate in an aqueous solution. Consider the stability of the anion i.e. the carboxylate anion. That's all. Yeah?

 

[nayryecal]

Understand the pKa trends. It's all about how readily the protons dissociate in an aqueous solution. Consider the stability of the anion i.e. the carboxylate anion. That's all. Yeah?

thank you!