Which of the following halides undergoes nucleophilic substitution most readily?

p - H_{3} C C_{6} H_{4} C l

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O - M e O C_{6} H_{4} C l

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p - C l C_{6} H_{4} C l

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C_{6} H_{5} C H (C l) C H_{3}

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Solution

The correct option is D $C_{6} H_{5} C H (C l) C H_{3}$
$C_{6} H_{5} C H (C l) C H_{3}$ undergoes nucleophilic substitution most readily as Cl is attached to aliphatic C atom.

In $p - H_{3} C C_{6} H_{4} C l, O - M e O C_{6} H_{4} C l, p - C l C_{6} H_{4} C l$ , Cl is attached to aromatic carbon atom. The nucleophilic substitution of aryl chlorides requires drastic conditions.

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