Which of the following compounds is most rapidly hydrolysed by $S_{N} 1$ mechanism?

C_{6} H_{5} C l

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C l - C H_{2} - C H = C H_{2}

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

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C_{6} H_{5} C H_{2} C l

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Solution

The correct option is C $(C_{6} H_{5})_{3} C C l$
The carbocation $(C_{6} H_{5})_{3} C^{+}$ obtained during $S_{N} 1$ reaction of $(C_{6} H_{5})_{3} C C l$ is stabilized by resonance with three phenyl groups. Hence, it is most stable and easily formed.
Due to this reason, $(C_{6} H_{5})_{3} C C l$ is most readily hydrolyzed by $S_{N} 1$ mechanism.

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C_{6} H_{5} - C H_{2} - B r

C H_{2} = C H - C H_{2} - B r

C H_{3} - C H (B r) C H_{3}

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