Question

The pk_aof acetone, CH₃COCH₃, is 19.3. Which of the following bases is strong enough to deprotonate acetone?

(b)$\mathit{N}{\mathit{a}}^{\mathbf{+}}{\mathbf{}}^{\mathbf{-}}\mathit{C}\mathbf{\equiv }\mathit{C}\mathit{H}$$\left({\mathrm{pk}}_a{H}_2{O}_2\mathrm{of}25\right)$

Short answer

Answer:

Yes, strong enough to deprotonate acetone due to more pk_athen acetone.

Step-by-step solution

pka of acetone

pk_ais a number that describes the acidity of the molecule lower the value of pk_astronger will be acidic and easily donate a proton and the higher the value of pk_aweaker will be the acid and stronger will be the conjugate base.

Acetone has a low value of pk_a then$N{a}^{+}{}^{-}C\equiv CH$

pka of Na+ -C≡CH

pk_aof$N{a}^{+}{}^{-}C\equiv CH$ is more than acetone so that $N{a}^{+}{}^{-}C\equiv CH$ is the weak acid and the strong conjugate base than acetone due to the strong conjugate base $N{a}^{+}{}^{-}C\equiv CH$ able to deprotonate the acetone.