Predict the direction of the following equilibrium and the approximate value of Keq.
$R - CO - C H_{2} - CO - R^{'}$ + $O H^{-}$ $⇌$ $R - CO - C H^{-} - CO - R^{'}$ + $H_{2} O$ ( $p K_{a}$ : beta-diketone = 9, $H_{2} O$ = 15.74)

Question

Predict the direction of the following equilibrium and the approximate value of Keq.

$R - CO - C H_{2} - CO - R^{'}$ + $O H^{-}$ $⇌$ $R - CO - C H^{-} - CO - R^{'}$ + $H_{2} O$ ( $p K_{a}$ : beta-diketone = 9, $H_{2} O$ = 15.74)

TestHub · Accepted Answer

The acid on the left is the beta-diketone ( p K a ​ 9) and the acid on the right is water ( p K a ​ 15.74). Water is the much weaker acid, so hydroxide deprotonates the diketone completely. Keq ≈ 1 0 15 ⋅ 74 − 9 = 1 0 6 ⋅ 74 ⋅

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