Which of the following is more readily hydrolysed by ${S_{N}}^{1}$ mechanism?

{(C_{6} H_{5})}_{2} C ({C H}_{3}) B r

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C_{6} H_{5} {C H}_{2} B r

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C_{6} H_{5} C H ({C H}_{3}) B r

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{(C_{6} H_{5})}_{2} C H B r

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Solution

The correct option is B ${(C_{6} H_{5})}_{2} C ({C H}_{3}) B r$
${(C_{6} H_{5})}_{2} C ({C H}_{3}) B r$ is more readily hydrolyzed by ${S_{N}}^{1}$ mechanism.

The carbocation intermediate ${(C_{6} H_{5})}_{2} C^{+} ({C H}_{3})$ is a tertiary carbocation and is stabilized by resonance with two benzene ring.

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