Organic chemistry: why is the carboxyl group acidic?
Tutoring chemistry, concepts arise. The tutor mentions an idea behind the acidity of the carboxyl group.
In my previous post I mention the carboxylic acid functional group. Yet, why is the carboxyl group acidic?
The reason I’ve heard is that the carboxyl group, being -COOH, is a carbon double-bonded to one oxygen atom and then single-bonded with another. This leads to very high electronegativity centred on the C atom. The result: the electron theoretically shared between the O and the H atom is drawn much toward the O atom. From the outside, therefore, the H atom appears as an unshielded proton, which attracts the negative end of a polar solvent like water.
In turn, the solvent molecules surround the H nucleus, their negative sides towards it, and pull it from the O. Said H nucleus, being just a proton, is the active ingredient of acidity in the context.
Source:
Solomons, T.W. Graham. Organic Chemistry, fourth edition. Toronto: John Wiley & Sons, 1988.
Jack of Oracle Tutoring by Jack and Diane, Campbell River, BC.
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