Predict the direction of the following equilibrium and the approximate value of Keq.
R₃COH + (enolate of a ketone R₂CH-CO-R') $⇌$ R₃CO⁻ + R₂CH₂-CO-R' (pKa ≈ 18 and ≈ 19)

Question

Predict the direction of the following equilibrium and the approximate value of Keq. R₃COH + (enolate of a ketone R₂CH-CO-R') ⇌ R₃CO⁻ + R₂CH₂-CO-R' (pKa ≈ 18 and ≈ 19)

TestHub · Accepted Answer

The acid on the left is the tertiary alcohol (pKa ≈ 18) and the acid on the right is the ketone α C-H (pKa ≈ 19). The weaker acid is on the right, so the equilibrium favours the products, but only modestly : Keq ≈ 10¹⁹⁻¹⁸ = 10.

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