Select the ether among following that yields methanol as one of the products on reaction with cold hydroiodic acid

Options

A. 1-methoxybutane
B. 1-methoxybutane-2-methylpropane
C. 2-methoxy-2-methylpropane
D. methoxybenzene

Answer

C

Explanation

According Zeisel method , when an ether reacts with cold , alkyl iodide and alcohol are formed . In case of asymmetrical ether , the alkyl halide is always formed from the smaller alkyl group provided no tertiary `(3^(@))` alkyl group is present and if any `3^(@)` alkyl group is present , the halogen gets attached with it . in case of alkyl aryl ethers the products are always phenol and an anlkyl halide .
(a) `CH_(3) - O - C_(4)H_(9) + HI overset("Cold")(to) CH_(3)I + C_(4) H_(9)OH`
(b) `CH_(3) - O - CH_(2) - underset(CH_(3))underset(|)(C)H - CH_(3) + HI overset("Cold")(to) CH_(3)I + CH_(3) - underset(CH_(3))underset(|)(C)H - CH_(3) - OH`