Explain why the pKa of benzoic acid (pKa = 4.2) is significantly lower than the

Question

Explain why the pKa of benzoic acid (pKa = 4.2) is significantly lower than the pKa of propanoic acid (pKa = 4.9). Select the single best answer.

a) Lower percentage s-character of benzoic acid's aromatic bond carbons destabilizes its conjugate base

b) Higher percentage s-character of benzoic acid's aromatic bond carbons destabilizes its conjugate base

c) Higher percentage s-character of benzoic acid's aromatic bond carbons stabilizes its conjugate base

d) Lower percentage s-character of benzoic acid's aromatic bond carbons stabilizes its conjugate base

Explanation / Answer

c) Higher percentage s-character of benzoic acid's aromatic bond carbons stabilizes its conjugate base

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