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Structural and Physical Properties of Carbonyls

A compound 'X...

Question

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 $60.$ Write chemical equations leading to the conversion of ' $X$ ' to ' $Y$ '.

A

C H_{3} C H_{2} - I H_{2} O - - \to C H_{3} C H_{2} - O H

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B

C H_{3} C H_{2} - O - C H_{2} C H_{3} H I - - \to 2 C H_{3} C H_{2} I

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C

C H_{3} - O - C H_{2} C H_{3} H I - - \to C H_{3} C H_{2} I + C H_{3} O H

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D

C H_{3} - O - C H_{2} C H_{3} H I - - \to C H_{3} C H_{2} O H + C H_{3} I

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Solution

The correct option is B $C H_{3} C H_{2} - O - C H_{2} C H_{3} H I - - \to 2 C H_{3} C H_{2} I$
Compound $X$ must be a symmetrical ether.
$\Rightarrow Acid is C H_{3} C O O H and Z = C H_{3} C H_{2} O H$

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

$C H_{3} C H_{2} - O (X) - C H_{2} C H_{3} H I - - \to 2 C H_{3} C H_{2} I (Y)$

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