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Chapter 2

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.