Question

Predict the product of the following reaction:

\[\ce{CH3 - CH2 - CH2 - O - CH3 + HBr ->}\]

Answer 1

Both the alkyl groups attached to oxygen are primary, so the Br⁻ ion will react with the smaller alkyl group (methyl group) to form propan-1-ol and bromomethane.

\[\ce{\underset{n-propyl methyl ether}{CH3 - CH2 - CH2 - O - CH3} + HBr ->[373 K] \underset{propan-1-ol}{CH3 - CH2 - CH2 - OH} + \underset{bromomethane}{CH3Br}}\]