[jcais]

Hello

I have a question for you all regarding incorporating an isotope into an alcohol. I just have to show the mechanism. I checked 2 textbooks and google but no help. You all have been very helpful in the past, so I turn here for help.

T-butyl alcohol is treated with H₂¹⁸O and sulfuric acid. The end product looks just like the beginning, but now the t-butyl alcohol has a 18 in front of the O for the isotope. How do you think this was done? How should I draw it?
__|__OH  H₂¹⁸O 
   |         H₂SO₄                                                    
--> __|__¹⁸OH
         | 
Thank you for your time and help.

[Fry]

Sulfuric acid protonates a tertiary alcohol.. protonating alcohols usually creates better leaving groups out of them.

You will end up with a t-butyl cation.. how will this react with the water isotope?

[AWK]

This is an equilibrium reaction. Heavy oxygen only partially replace light oxygen in t-BuOH.