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Q. One mole of an organic compound $'A'$ with the formula $C_3H_8O$ reacts completely with two moles of $HI$ to form $X$ and $Y$. When $Y$ is boiled with aqueous alkali forms $Z. Z$ answers the iodoform test. The compound $A$ is

KCETKCET 2010Alcohols Phenols and Ethers

Solution:

Molecular formula $C _{3} H _{8} O \left( C _{n} H _{2 n+2} O \right)$ suggests that the organic compound is either alcohol or ether.

Since, the compound on reaction with HI gives two different compounds, it must be an unsymmetrical ether, and its formula must be $CH _{3} OC _{2} H _{5}$ (methoxyethane).

The reactions are as follows.

$\underset{\text { methoxyethane }}{ CH _{3} OC _{2} H _{5}}+2 HI \longrightarrow \underset{X}{ CH _{3}} I + \underset{Y}{C _{2} H _{5} OH}$

$C _{2} H _{5} OH +\underset{\text { (aqueous) }}{ NaOH }+ I _{2} \longrightarrow \underset{\text { iodoform }}{ CHI _{3}}+ HCOONa$

$+ H _{2} O + NaI$