Question:

Both ethanol and ethanoic acid exhibit acidic properties, the former is more acidic than the latter

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Focus on the ground state and conjugate base state and explain why ethanoic acid is stronger acid than ethanol

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  1. When ethanol reacts with a base, the (-)-charge is concentrated on the O. This means that it is capable of pulling the H+ back from the base (conjugate aqcid):

    CH3CH2-OH + :B ===> CH3CH2-O(-) + BH(+)

    With ethanoic (acetic) acid, the (-) charge is distributed by resonance over two O's, so the intensity of the charge on each is half as much:

    CH3-COOH + :B ===> CH3-COO(-) + BH(+)

    O=C-O(-) <===> (-)O-C=O

    (You should imagine CH3- also connected to that middle carbon. I can't fit it in.)

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