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Among the following ethers, which one will produce methyl alcohol on treatment with hot concentrated HI?
A
- 
B
$CH_3-CH_2-CH_2-CH_2-O-CH_3$
C
- 
D
- 
Detailed Solution
C–O bond cleavage of an ether can follow $S_N1$ or $S_N2$. If one group can form a stable carbocation, such as tert-butyl, the reaction follows the $S_N1$ mechanism.
$(CH_3)_3C-O-CH_3 \xrightarrow{\text{hot conc. HI}} (CH_3)_3C-\overset{+}{O}(H)-CH_3 \rightarrow (CH_3)_3C^+ + CH_3OH$
$(CH_3)_3C^+ + I^- \rightarrow (CH_3)_3C-I$
So methyl alcohol is produced.
$(CH_3)_3C-O-CH_3 \xrightarrow{\text{hot conc. HI}} (CH_3)_3C-\overset{+}{O}(H)-CH_3 \rightarrow (CH_3)_3C^+ + CH_3OH$
$(CH_3)_3C^+ + I^- \rightarrow (CH_3)_3C-I$
So methyl alcohol is produced.