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An ether ‘A’ on treatment with PCl₅ produces two different chloro compounds B and C. Each of the product separately on reacting with sodium in dry ether produce n-butane and 2,3-dimethyl butane respectively. Then the probable structure of ether ‘A’ is

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${({CH}_{3} - {CH}_{2})}_{2} - CH - O - {CH}_{2} - {CH}_{3}$

${({CH}_{3})}_{2} CH - O - {CH}_{2} - {CH}_{3}$

${({CH}_{3})}_{3} C - O - {CH}_{2} - {CH}_{3}$

${({CH}_{3})}_{2} - CH - {CH}_{2} - O - {CH}_{2} - {CH}_{3}$

answer is B.

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Detailed Solution

$\underset{Isopropyl ethyl ether}{{({CH}_{3})}_{2} CH - O - {CH}_{2} - {CH}_{3} \overset{{PCl}_{5}}{\to}} \underset{Isopropyl chloride}{{({CH}_{3})}_{2} CH - Cl} + \underset{ethyl chloride}{H_{3} C - {CH}_{2} - Cl}$

${({CH}_{3})}_{2} CH - Cl \to_{dry ether}^{Na} \underset{2, 3 - dimethyl butane}{H_{3} C - CH ({CH}_{3}) - CH ({CH}_{3}) - {CH}_{3}}$

$H_{3} C - {CH}_{2} - Cl \to_{dry ether}^{Na} \underset{n - butane}{H_{3} C - {CH}_{2} - {CH}_{2} - {CH}_{3}}$

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