Ochem Acid strength

[dane4695]

Why would something liek acetic acid be a stronger acid than phenol? Shouldn't phenol have more resonance structures?

Anyone have a good website for acid strength practice problems?

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[coodoo]

Why would something liek acetic acid be a stronger acid than phenol? Shouldn't phenol have more resonance structures?

Anyone have a good website for acid strength practice problems?

The negative charge flows b/w two oxygen atoms making the deprotanation of the carboxylic acid high favorable energetically. For more information, take a bioenergetics course in school

 

[dane4695]

I understand that there is resonance of the negative charge... but shouldn't that also be the case in phenol? 4 res structures vs 2? Or maybe i'm missing something.

 

[coodoo]

I understand that there is resonance of the negative charge... but shouldn't that also be the case in phenol? 4 res structures vs 2? Or maybe i'm missing something.

it's right there in my statement. it resonates b/w two OXYGEN atoms. oxygen is more electronegative than carbon is, and hence the reaction of deprotanation is energetically more favorable

 

[dane4695]

Ahh. I see. Thanks. Didn't realize inductive effect was so powerful.

 

[coodoo]

Ahh. I see. Thanks. Didn't realize inductive effect was so powerful.