Which of the following most readily undergoes nucleophilic substitution?

{C H}_{2} = C H C l

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{C H}_{3} C H = C H C l

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H_{2} C = C H C (C l) = {C H}_{2}

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{C H}_{2} = C H {C H}_{2} C l

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C_{6} H_{5} C l

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Solution

The correct option is D ${C H}_{2} = C H {C H}_{2} C l$
The compound of option D (allyl chloride) is most reactive. Hence, it will undergo nucleophilic substitution most readily.
When it loses a chloride ion, the carbocation intermediate is stabilized by resonance.
$C H_{2} = C H - C H_{2}^{+} \leftarrow \to^{+} C H_{2} - C H + C H_{2}$

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