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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap215

An ether X, $C X_{5} H X_{12} O$ , does not react with sodium metal. With one equivalent of $HI$ it gives a tertiary alkyl iodide and methanol. X is

Atert-butyl methyl ether
Bethyl isopropyl ether
Cbutyl methyl ether
Dsec-butyl methyl ether

Answer: A

No reaction with Na shows X is an ether. A tertiary iodide and methanol come from SN1 cleavage of a tert-alkyl methyl ether. With C5H12O,

(CH X_{3}) X_{3} C - O - CH X_{3}

gives

(CH X_{3}) X_{3} C - I

and

CH X_{3} OH

; the other isomers cleave by SN2 and do not give a tertiary iodide.

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