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  4. Reaction of which among the following ethers with HI in cold leads to formation of methyl alcohol ?

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Q. Reaction of which among the following ethers with $HI$ in cold leads to formation of methyl alcohol ?

MHT CETMHT CET 2015

Solution:

When asymmetrical ether undergoes reaction with HI in cold, bulkier group forms its iodide and smaller group forms its alcohol, whereas if normal alkyl group present in ether, smaller group forms its iodide.

$\underset{\text{Ethyl methyl ether}}{C_2H_5 - O - CH_3} \ce{->[HI]} \underset{\text{Ethyl alcohol}}{CH_3I + C_2H_5OH}$

$\underset{\text{Methyl propyl ether}}{CH_3 - O - CH_2 -CH_2 -CH_3} \ce{->[HI]}$

$\underset{\text{Propyl alcohol}}{CH_3I + CH_3CH_2CH_2OH}$

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