[rleung]

Hi,

I am confused as to why the compound on the right is more acidic than the one on the left.  I would've thought that the one on the right is more acidic since the e- are delocalized between 2 O's, whereas they are not in the structure on the left.  My book says the one on the left is more acidic since the negatively-charged compound on the right has a greater amount of elecron donation by resonance, but I don't understand how electron donation has anything to do with these types of molecules (I thought electron donation only applies to benzene rings).  Thank you so much.

Ryan

[Mitch]

You have an acid with its conjugate base. Don't let the organic structure of these molecules confuse you from your knowledge of general chemistry

[forislam20]

*ON COMPARING ACIDITY U MUST LOOK AT THE CONJUGATE BASE OF THE ACID FOR STRUCTURE NO 1 THE CONJUGATE BASE AS SHOWN BELOW WILL BE STABILIZED BY 1) HYDROGEN BONDING
2)THE ORIGINAL ACID ITSELF TENDS TO GIVE A PROTON SINCE THE CARBOXYLIC GP IS AN ELECTRON WITHDRAWING GP
*BUT LOOK AT STRUCTURE NO 2 AS SHOWN BELOW 1)THE HYDROGEN BONDING STABILIZING IT WILL INTERFER WITH THE DONATION OF A SECOND PROTON
2)IN ADDITION IF U KNOW THE CARBOXYLATE GP IS AN ELECTRON DONATING GP

I HOPE IT IS CLEAR NOW !!1!

[rleung]

Thanks so much