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(A) The rate of $S_{N}1$ reaction depends on the stability of the carbocation intermediate formed after the departure of the leaving group.More stable

Vedclass · Accepted Answer

$(C_6H_5)_2C(CH_3)Br$

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(A) The rate of $S_{N}1$ reaction depends on the stability of the carbocation intermediate formed after the departure of the leaving group.More stable the carbocation,faster is the hydrolysis.Comparing the carbocations formed from the given halides:$(a)$ $(C_6H_5)_2C^+(CH_3)$ is a tertiary benzylic carbocation stabilized by two phenyl rings and one methyl group.$(b)$ $C_6H_5CH_2^+$ is a primary benzylic carbocation.$(c)$ $C_6H_5CH^+(CH_3)$ is a secondary benzylic carbocation.$(d)$ $(C_6H_5)_2CH^+$ is a secondary benzylic carbocation stabilized by two phenyl rings.The tertiary benzylic carbocation $(C_6H_5)_2C^+(CH_3)$ is the most stable among the given options due to maximum resonance stabilization and inductive effect.Therefore,$(C_6H_5)_2C(CH_3)Br$ is most readily hydrolysed by $S_{N}1$ mechanism.

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

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