Consider the reaction: $CH_3CH_2OCH_2CH_3 + HI \xrightarrow{Heat}$. The products formed are:
When symmetrical ethers react with HI, the C-O bond breaks, forming an alcohol and an alkyl iodide. If excess HI is present and heated, the alcohol can further react to form alkyl iodide. However, with limited HI, ethanol and iodoethane are the primary products. The provided example 7.7 (i) shows $CH_3CH_2 – O – CH_2CH_3$ reacting with HI to give $CH_3CH_2OH$ and $CH_3CH_2I$.