If I treat my 1 hexanol with an acid strong enough to protonate the primary alcohol, turn it into a good leaving group, have a hydride shift, and then have water perform a nucleophilic attack on the now secondary carbocation, and then have another water molecule come and deprotonate the newly attached one with positive charge, to form 2-hexanol. Why would this not work?
The book chose different reagents and if I try to follow through with their synthesis I get a bit stuck.
From what I follow, they treated the primary alcohol with an PBr3 to convert the alcol into a good leaving group and ultimately underwent Sn2 to form a primary alkyl bromide. Then they took this alkyl bromide, treated it with sodium tertbutoxide , underwent another Sn2 and ended up with a hexyl tert butyl ether.
From their they treated with H2O, H2SO4 cat.
I am not sure where to go from here. Do I just protonate the ether using a proton from the sulfuric acid, and somehow end up cleaving it? I am really not sure what to do here.
I have a midterm coming up really soon so any help is greatly appreciated. Sorry if the pictures are kind of blurry.
Thanks in advance