Question

The pk_aof acetone, $\mathit{C}{\mathit{H}}_{\mathbf{3}}\mathit{C}\mathit{O}\mathit{C}{\mathit{H}}_{\mathbf{3}}$, is 19.3. Which of the following bases is strong enough to deprotonate acetone?

(c) $\mathit{N}\mathit{a}\mathit{H}\mathit{C}{\mathit{O}}_{\mathbf{3}}$($\mathit{p}{\mathit{k}}_{\mathbf{a}}$of H₂CO₃6.4)

Short answer

Answer:

Not strong enough to deprotonate acetone due to less 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_a stronger will be acidic and easily donate a proton and higher the value of pk_aweaker will be the acid and stronger will be the conjugate base.

Acetone has high value of pk_athen NaHCO₃

pka of NaHCO3

pk_aof NaHCO₃is less than acetone, so that NaHCO₃is the strong acid and the weak conjugate base than acetone due to weak conjugate base NaHCO₃ not able to deprotonate the acetone.