Alcohols and Ethers - Result Question 58
####63. A compound ’ $X$ ’ containing $C, H$ and $O$ is unreactive towards sodium. It does not add with bromine. It also does not react with Schiff’s reagent. On refluxing with an excess of $HI$, ’ $X$ ’ yields only one organic product ’ $Y$ ‘. ’ $Y$ ’ on hydrolysis yields a new compound ’ $Z$ ’ which can be converted into ’ $Y$ ’ by reaction with red phosphorus and iodine. The compound ’ $Z$ ’ on oxidation with potassium permanganate gives a carboxylic acid. The equivalent weight of acid is 60 . What are the compounds ’ $X$ ‘, ’ $Y$ ’ and ’ $Z$ ‘? Write chemical equations leading to the conversion of ’ $X$ ’ to ’ $Y$ ‘.
$(1981,3 M)$
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Solution:
- Compound $X$ must be a symmetrical ether :
$R \underset{X}{O-} R \xrightarrow{HI} \underset{Y}{2 R-} I \xrightarrow{Na}$ No reaction, not an alcohol $\xrightarrow[\text { reagent }]{\text { Schiffs’ }}$ No reaction, not an aldehyde.
$\Rightarrow$ Acid is $CH _3 COOH$ and $Z=CH _3 CH _2 OH$
$\Rightarrow X=C _2 H _5-O-C _2 H _5, Y=CH _3-CH _2-I$
