If an ether with a tertiary alkyl group on one side and a methyl group on the other ($CH_3OC(CH_3)_3$) reacts with HI, which bond will preferentially cleave?
While the NCERT example shows specific cleavage at the less hindered side for $S_N2$, for tertiary alkyl groups, the reaction with HI often proceeds via an $S_N1$ mechanism. The tertiary carbocation formed is highly stable, leading to the formation of the tertiary alkyl iodide. The context implies the general principle of bond cleavage with HI.