The pKa for t-butyl alcohol is 18, can a solution oft-butoxide be prepared using

Question

The pKa for t-butyl alcohol is 18, can a solution oft-butoxide be prepared using water as the solvent, why or why not?Use structures and reactions to justify your answer. Again, this was taken from a practice exam, any help isappreciated and I promise to rate. Thanks. The pKa for t-butyl alcohol is 18, can a solution oft-butoxide be prepared using water as the solvent, why or why not?Use structures and reactions to justify your answer. Again, this was taken from a practice exam, any help isappreciated and I promise to rate. Thanks.

Explanation / Answer

You must compare the pKa of the bronstedacid and the conjugate acid to see if the reactionsucceeds. The conjugate acid must beweaker in order for the reaction to proceedsuccessfully. t-butanol (acid) + H2O (base) ------> t-butoxide(conjugate base) + H3O+ (conjugate acid) The pKa of t-butanol is 16, while the pKa of hydronium is about-1.9 (very low basically). Thus, water cannot be used to deprotonate t-butanol efficientlysince the conjugate acid is stronger thant-butanol.

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