What is the major product of the following reaction sequence?
$H O - C H_{2} - O | | C - O H S O C l_{2} - --- \to excess C H_{3} O N a - ---- \to 1 eqv.$

C l - C H_{2} - O | | C - C H_{3}

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C l - C H_{2} - O | | C - O C H_{3}

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C H_{3} O - C H_{2} - O | | C - C H_{3}

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C H_{3} O - C H_{2} - O | | C - C l

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Solution

The correct option is B $C l - C H_{2} - O | | C - O C H_{3}$
$H O - C H_{2} - O | | C - O H S O C l_{2} - --- \to excess C l - C H_{2} - O | | C - C l$

$C l - C H_{2} - O | | C - C l C H_{3} O N a - ---- \to 1 eqv. C l - C H_{2} - O | | C - O C H 3$

Acyl chloride is more reactive because carbonyl carbon is more electrophilic and less hindered than alkyl chloride hence substitution takes place at carbonyl centre.

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