Question 13.4: Predicting the Product of an Ether Cleavage Reaction Predict...

Predicting the Product of an Ether Cleavage Reaction

Predict the products of the following reaction:

Strategy
Identify the substitution pattern of the two groups attached to oxygen—in this case a tertiary alkyl group and a primary alkyl group. Then recall the guidelines for ether cleavages. An ether with only primary and secondary alkyl groups usually undergoes cleavage by S_{N}2 attack of a nucleophile on the less hindered alkyl group, but an ether with a tertiary alkyl group usually undergoes cleavage by an S_{N}1 mechanism. In this case, an S_{N}1 cleavage of the tertiary C–O bond will occur, giving propan-1-ol and a tertiary alkyl bromide.