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Q. $CH _{3} OC _{2} H _{5}$ and $\left( CH _{3}\right)_{3} C - OCH _{3}$ are treated with hydroiodic acid. The fragments after reactions obtained are

AIIMSAIIMS 2007Alcohols Phenols and Ethers

Solution:

When mixed ethers are used, the alkyl iodide produced depends on the nature of alkyl groups. If one group is Me and the other a pri-or sec-alkyl group, then methyl iodide is produced. Here reaction occurs via $S _{ N } 2$ mechanism and because of the steric effect of the larger group, $I ^{-}$ attacks the smaller (Me) group.

$CH _{3} OC _{2} H _{5}+ HI \rightarrow CH _{3} I + C _{2} H _{5} OH$

When the substrate is a methyl $t$ -alkyl ether, the products are $t-R I$ and MeOH. Here reaction occurs by $S_{N} !$ mechanism and formation of products is controlled by the stability of carbocation. Since carbocation stability

order is $3^{\circ}>2^{\circ}>1^{\circ}> \overset{\oplus}{CH _{3}}$

$\therefore $ Alkyl halide is always derived from tert-alkyl group.

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