Question

Among the following ethers, which one will produce methyl alcohol on treatment with hot concentrated HI?

• A.
• B.
• C.
• D.

Answer 1

The correct option is A

Ether on reaction with HI undergoes $S_{N}2$ or $S_{N}1$ reaction depends on the nature substrate. If any one group can form stable carbocation like tertiary butyl group then reaction follow's $S_{N}1$ mechanism.

Compound (a), (b) and (c) on $S_{N}1$ mechanism forms primary and secondary carbocation which are less stable and these compound prefers to go by $S_{N}2$ mechanism, thus, $I^{-}$ gets attached to less susbstituted site to form methyl iodide instead of methanol.
Hence, option (d) is the correct answer.