Which of the given pair of $S_{N} 1$ reaction would you expect to proceed faster?

(II) > (I)

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(II) < (I)

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(I) = (II)

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Cannot be determined

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Solution

The correct option is A (II) > (I)
The reaction with $H B r$ is faster than the reaction with $N a B r$ . $H B r$ protonates the oxygen atom of tert-butyl alcohol and helps in the formation of tert butyl carbocation (by loss of molecule of water) which is the rate determining step.
Hence, option (a) is correct.

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