OH но. HO phthalic acid isophthalic acid pKa1 = 2.9 pK22 = 5.4 pKa1 = 3.7 pKa2 = 4.6

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Phthalic acid and isophthalic acid have protons on two carboxy groups that can be removed with base. (a) Explain why the pKa for loss of the first proton (pKa1) is lower for phthalic acid than isophthalic acid. (b) Explain why the pKa for loss of the second proton (pKa2) is higher for phthalic acid than isophthalic acid.

OH
но.
HO
phthalic acid
isophthalic acid
pKa1 = 2.9
pK22 = 5.4
pKa1 = 3.7
pKa2 = 4.6
Transcribed Image Text:OH но. HO phthalic acid isophthalic acid pKa1 = 2.9 pK22 = 5.4 pKa1 = 3.7 pKa2 = 4.6
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Phthalic acid and isophthalic acid have protons on two carboxy groups that can be removed with base.

(a) Why the pKa for loss of the first proton (pKa1) is lower for phthalic acid than isophthalic acid has to be explained.

(b) Why the pKa for loss of the second proton (pKa2) is higher for phthalic acid than isophthalic acid has to be explained.

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