Measure of dissociation:
The acidity constant is as well a measure of dissociation and of how acidic a specific acid is. The stronger the acid, the much more it is ionized and the better concentration of products in the above equation. The meaning of this is that a strong acid has a high Ka value. The Ka values for the subsequent ethanoic acids are in brackets and illustrate that the strongest acid in the series is trichloroacetic acid.
CI3CCO2H (23200 * 10-5) > CI2CHCO2H (5530 * 10-5) > CICH2CO2H (136*10-5) > CH3CO2H (1.75*10-5)
Ka values are strange to work with and thus it is more general to measure the acidic strength as a pKa value than Ka. The pKa is the negative logarithm of Ka (pKa = log10 Ka) and results in much more manageable numbers. The pKa values for every of the above ethanoic acids are displayed in brackets below. The strongest acid (trichloroacetic acid) comprises the lowest pKa value.
Cl3CCO2H (0.63) < Cl2CHCO2H (1.26) < ClCH2CO2H (2.87) < CH3CO2H (4.76).
Hence the stronger the acid, the higher the value of Ka, and the lower the value of pKa. An amine like ethylamine (CH3CH2NH2) is a very weak acid (pKa = 40) as compared to ethanol (pKa = 16). This is because of the relative electronegativities of oxygen and nitrogen as explained above. Though, the electronegativity of neighboring atoms is not just only the effect on acidic strength. For instance, the pKa values of ethanoic acid (4.76), ethanol (16), and phenol (10) depict that ethanoic acid is very much acidic as compare to the phenol, and that phenol is much more acidic as compared to the ethanol. The variation in acidity is quite marked, yet hydrogen is attached to oxygen in all three structures.
Likewise, the ethanoic acids Cl3CCO2H (0.63), ClCH2CO2H (2.87), Cl2CHCO2H (1.26), and CH3CO2H (4.76) have considerably different pKa values and still the acidic hydrogen is attached to an oxygen in each of these structures. Hence, factors other than electronegativity have a task to play in determining acidic strength.