The reagent boron tribromide (BBr3) is used to cleave ethers, producing alcohols and alkyl halide after a subsequent hydrolysis reaction. The general reaction sequence is shown below:
The mechanism involves a bromide ion attacking the Lewis acid–base adduct of the ether with BBr3. Suggest a mechanism for the reaction of ethyl propyl ether with BBr3 and a subsequent hydrolysis reaction to produce propan-1-ol and bromoethane.