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

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

MHT CETMHT CET 2014

Solution:

According Zeisel method, when an ether reacts with cold $HI$, 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 $\left(3^{\circ}\right)$ alkyl group is present and if any $3^{\circ}$ alkyl group is present, the halogen gets attached with it. In case of alkyl aryl ethers, the products are always phenol and an alkyl halide.

(a) $CH _{3}- O - C _{4} H _{9}+ HI \stackrel{\text { Cold}}{\longrightarrow } CH _{3} I + C _{4} H _{9} OH$

(b) $CH_3— O— CH_2 — \underset{\overset{|}{C}H_3}{CH}— CH_3 + HI \stackrel{\text{Cold}}{\longrightarrow }$

$CH_3I + CH_3— \underset{\overset{|}{C}H_3}{CH}— CH_3— OH$

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