Predict the direction of the following equilibrium and the approximate value of Keq.
R-CO-CH₂-CO-R' + R₃N $⇌$ R-CO-CH⁻-CO-R' + R₃NH⁺ (pKa : beta-diketone = 9, R₃NH⁺ ≈ 12)

Question

Predict the direction of the following equilibrium and the approximate value of Keq. R-CO-CH₂-CO-R' + R₃N ⇌ R-CO-CH⁻-CO-R' + R₃NH⁺ (pKa : beta-diketone = 9, R₃NH⁺ ≈ 12)

TestHub · Accepted Answer

The acid on the left is the beta-diketone (pKa 9) and the acid on the right is the trialkylammonium ion (pKa ≈ 12). The weaker acid is on the right, so the products are favoured. Keq ≈ 10¹²⁻⁹ = 10³·

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