SATHEE: Alcohols and Ethers - Result Question 58

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 $H I$ , ’ $X$ ’ 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 :

$R \underset{X}{O -} R \overset{H I}{\to} \underset{Y}{2 R -} I \overset{N a}{\to}$ No reaction, not an alcohol $\to_{reagent}^{Schiffs’}$ No reaction, not an aldehyde.

$\Rightarrow$ Acid is $C H_{3} C O O H$ and $Z = C H_{3} C H_{2} O H$

$\Rightarrow X = C_{2} H_{5} - O - C_{2} H_{5}, Y = C H_{3} - C H_{2} - I$

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