Solving SN1 Reaction: t-Butyl Bromide & HOH

[daniel6874]

tert-butyl bromide reacts with HOH to give HBr and the corresponding alcohol ,
C
C-C-C
OH

But tert-butyl alcohol reacts with HCl to give tert-butyl chloride.

HBr is a "stronger" acid than HCl. Is this part of the explanation of the different reactions?

 

[DGJNAc]

In order to get ^tBuX [X=Cl, Br] from the corresponding alcohol, you need to use conc. HX. If the proportion of water is too high (i.e. the concentration of X^- is low] you will mostly have the alcohol in the equilibrium mixture. This is why when you treat ^tBuX [X=Cl, Br] with water you get hydrolysis - water is in vast excess compared to Br^- at equilibrium.