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## Q. 2.4

Predicting acid Strengths from $p K_{ a }$ Values

Water has $p K_{ a } = 15.74$, and acetylene has $p K_{ a } = 25$. Which is the stronger acid? Does hydroxide ion react with acetylene?

S t r a t e g y
In comparing two acids, the one with the lower $pK_{a}$ is stronger. Thus, water is a stronger acid than acetylene and gives up $H^{+}$ more easily.

## Verified Solution

Because water is a stronger acid and gives up $H^{+}$ more easily than acetylene does, the $HO^{-}$ion must have less affinity for $H^{+}$ than the $HC=C:^{-}$ ion has. In other words, the anion of acetylene is a stronger base than hydroxide ion, and the reaction will not proceed as written.