Citrus fruits are rich in citric acid, a compound with three COOH groups. Explain the following: a. The first pKa (for the COOH group in the center of the molecule) is lower than the pKa of acetic acid. b. The third pKa is greater than the pKa of acetic acid.

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05-02-2020
Chemistry

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Citrus fruits are rich in citric acid, a compound with three COOH groups. Explain the following: a. The first pKa (for the COOH group in the center of the molecule) is lower than the pKa of acetic acid. b. The third pKa is greater than the pKa of acetic acid.

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okekeadaobi55 okekeadaobi55 · Answer 1 · 2020-02-06T15:56:47+01:00

Answer:

a. the first pKa is lower because of the presence of an electron withdrawing 'OH' group attached to the carbon that is directly attached to it.

b. the third pKa is greater than that of acetic acid because of the presence of an electron donating methyl group which is directly attached to it.

Explanation:

Induction or Inductive effect is the electronic effects an atom or a group of atoms exert on a compound or a portion of a compound, which could either be electron donating or electron withdrawing, thereby affecting its acidity or basicity.

Electronegativity confers acidity on a compound. In a, the OH group withdraws electrons from the COOH group, conferring more electronegativity on the middle COOH group, thereby reducing the pKa and thus increasing acidity.

In b, the electron donating effect of the methyl group, decreases the electronegativity of the COOH group,p thereby increasing the pKa which also means decreased acidity.