Which one of the following is more readily hy | vedclass

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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.Greater sta

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.Greater stability of the carbocation leads to a faster reaction.The carbocations formed from the given halides are:$A$: $(C_6H_5)_2C^+(CH_3)$ (Tertiary benzylic carbocation,stabilized by two phenyl rings and one methyl group)$B$: $C_6H_5CH_2^+$ (Primary benzylic carbocation)$C$: $C_6H_5CH^+(CH_3)$ (Secondary benzylic carbocation)$D$: $(C_6H_5)_2CH^+$ (Secondary benzylic carbocation,but less stable than $A$ due to lack of the electron-donating methyl group)Comparing the stability,the tertiary benzylic carbocation $(C_6H_5)_2C^+(CH_3)$ is the most stable due to resonance and the inductive effect of the methyl group.Thus,$(C_6H_5)_2C(CH_3)Br$ is most readily hydrolysed by the $S_{N}1$ mechanism.

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

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