Background: Upon addition of water to acetone solution of tert-butyl chloride, t

Question

Background: Upon addition of water to acetone solution of tert-butyl chloride, the tert-butyl chloride will undergo hydrolysis in a few minutes to produce tert-butyl alcohol.

I have two questions I am trying to answer.

1. If 5.0mL of your acetone solution of t-butyl chloride in acetone undergoes hydrolysis completely with 5.0mL of water, how many moles of HCl will be produced?

2. Calculate the pH of the solution.

Thank you for any help. If you could show the work and a brief explanation, it would be appreciated.

Explanation / Answer

In acetone solution, the following reaction takes place :

tert-butyl chloride + H2O ----------------> tert-butyl alcohol + HCl

i.e. 1 mole(22.4 L) of tert-butyl chloride hydrolysis with 1 mole(22.4 L) of H2O to give 1 mole(22.4 L) of tert-butyl alcohol and 1 mole(22.4 L) of HCl

So, 5.0 mL of HCl is formed. i.e. 5/22400 = 2.23*10^-4 moles of HCl

Molarity of HCl = 2.23*10^-4/0.01 = 0.0223 M HCl

therefore, the [H+] = 0.0223 M

pH = - log [0.0223] = 1.65

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