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

Options

A. `CH_3 - underset(CH_3)underset(|)(CH) - CH_2 - O - CH_3`
B. `CH_3 - CH_2 - CH_2 - CH_2 - O -CH_3`
C. `CH_3 - CH_2 - underset(CH_3)underset(|)(CH) - O - CH_3`
D. `CH_3 - underset(CH_3)underset(|)overset(CH_3)overset(|) -C - O - CH_3`

Answer

D

Explanation

C - O bond cleavage of ether depends on mechanism involved in reaction which can be `SN^1 or SN^2` . If any one group can form stable carbocation like tertiary butyl group then reaction follows `SN^1` mechanism.