Chapter 11, Problem 11.6P

Which bases can deprotonate acetylene? The $\text{p}{K}_{\text{a}}$ values of the conjugate acids are given in parentheses.

a. ${\text{CH}}_{\text{3}}{\text{NH}}^{-}\left(\text{p}{K}_{\text{a}}=40\right)$

b. ${\text{CO}}_3^{2-}\left(\text{p}{K}_{\text{a}}=10.2\right)$

c. ${\text{CH}}_{\text{2}}={\text{CH}}^{-}\left(\text{p}{K}_{\text{a}}=44\right)$

d. ${\left({\text{CH}}_{\text{3}}\right)}_3{\text{CO}}^{-}\left(\text{p}{K}_{\text{a}}=18\right)$