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JEE Advanced levelSingle correct optionDifficulty 3 of 3o3037

Chloromethyl methyl ether, $CH X_{3} - O - CH X_{2} - Cl$ , is stirred with excess water. The organic products at the end of the reaction are

Amethoxymethanol ( $CH X_{3} OCH X_{2} OH$ ) only, which is stable
Bdimethyl ether and formic acid
Cethanol and $HCl$
Dmethanol and methanal, with $HCl$

Answer: D

Loss of chloride is assisted by the oxygen lone pair, giving the oxocarbenium ion

CH X_{3} - O X^{+} = CH X_{2}

. Water adds to give the hemiacetal

CH X_{3} O - CH X_{2} - OH

, which is unstable and breaks down into

CH X_{3} OH

and

HCHO

. The

HCl

is released as a by-product.

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