need simple organic chem help

[toph99]

I'm at a friend's house and we're trying to finish a chem lab for tomorrow, but we have come upon a question and have no idea what the answer to the question. Why does 2-methyl-2-propanol go through halogenation when HCl is added, but 1-butanol and 2-butanol do not. I know someone out there remembers their highschool chem so give us a hand

 

[toph99]

bump

c'mon we're in desparate need of help!

 

[toph99]

someone help us pleeeeeeeeeeeeeeeeease

 

[tsunek]

the alcohol on the 2-methyl 2 propanol is tertiary. this would operate by the sn1 mechanism which doesn't operate on primary alcohols. halogenation of the other 2 alcohols could occur through an sn2 mechanism