Predict the direction of the following equilibrium and the approximate value of Keq.
R-CO-OR' + H₂SO₄ $⇌$ R-CO(⁺H)-OR' + HSO₄⁻ (pKa : H₂SO₄ = -9, protonated ester ≈ -6)

Question

Predict the direction of the following equilibrium and the approximate value of Keq. R-CO-OR' + H₂SO₄ ⇌ R-CO(⁺H)-OR' + HSO₄⁻ (pKa : H₂SO₄ = -9, protonated ester ≈ -6)

TestHub · Accepted Answer

The acid on the left is H₂SO₄ (pKa -9) and the acid on the right is the protonated ester (pKa ≈ -6). The protonated ester is the weaker acid, so the products are favoured. Keq ≈ 10^(-6-(-9)) = 10³·

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