The lab is to create 1-Bromobutane from 1-Butanol. Dibutyl ether is a side product you want to remove.
The Attempt at a Solution
9M H2SO4, KBr and 1-Butanol are refluxed for 45 mins. After distillation, you place 10 ml of cold 1M H2SO4 acid into the distillate. The organic layer contains 1-Bromobutane and the dibutyl ether in the aqueous layer is removed. Why do you need to treat the 1-Bromobutane with NaOH to purify the solution? Wouldn't NaOH do an Sn2 reaction and get us right back to the starting point?