Which one of the following is more readily hydrolysed by $\mathrm{S}_{\mathrm{N}} 1$ mechanism?

1. $\left(\mathrm{C}_6 \mathrm{H}_5\right)_2 \mathrm{C}\left(\mathrm{CH}_3\right) \mathrm{Br}$
2. $\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}_2 \mathrm{Br}$
3. $\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}\left(\mathrm{CH}_3\right) \mathrm{Br}$
4. $\left(\mathrm{C}_6 \mathrm{H}_5\right)_2 \mathrm{CHBr}$

Solution

The order of reactivity of halides towards $\mathrm{S}_{\mathrm{N}} 1$ reaction is $ \text { benzyl }>\text { allyl }>3^{\circ}>2^{\circ}>1^{\circ}>\mathrm{Me} $ Therefore, the order of hydrolysis by $\mathrm{S}_{\mathrm{N}} 1$ mechanism is

Asked in: AP EAMCET 2014

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