Which one of the following chlorohydrocarbons | vedclass

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(B) Solvolysis proceeds via an $S_N1$ mechanism,which involves the formation of a carbocation intermediate. The rate of solvolysis depends on the stab

Vedclass · Accepted Answer

$C_6H_5CH_2Cl$

Vedclass · Answer

(B) Solvolysis proceeds via an $S_N1$ mechanism,which involves the formation of a carbocation intermediate. The rate of solvolysis depends on the stability of the carbocation formed.$(a)$ $C_6H_5Cl$: The carbocation formed would be a phenyl cation,which is highly unstable.$(b)$ $C_6H_5CH_2Cl$: The carbocation formed is $C_6H_5CH_2^+$,which is resonance-stabilized by the benzene ring (benzylic carbocation). This is the most stable among the options.$(c)$ $C_6H_5CH_2CH_2Cl$: The carbocation formed is a primary alkyl carbocation,which is less stable than the benzylic carbocation.$(d)$ $CH_2=CHCl$: The carbocation formed would be a vinyl cation,which is highly unstable due to the $sp$ hybridization of the positively charged carbon.Therefore,$C_6H_5CH_2Cl$ readily undergoes solvolysis.

Which one of the following chlorohydrocarbons readily undergoes solvolysis?

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