The organic halide,which does not undergo hyd | vedclass

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(D) $S_{N}1$ mechanism proceeds via the formation of a carbocation intermediate. The stability of the carbocation determines the ease of the $S_{N}1$

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$CH_3-CH=CH-Cl$

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(D) $S_{N}1$ mechanism proceeds via the formation of a carbocation intermediate. The stability of the carbocation determines the ease of the $S_{N}1$ reaction. $(A)$ Benzyl chloride forms a benzyl carbocation $(C_6H_5CH_2^+)$,which is resonance-stabilized by the benzene ring. $(B)$ $CH_2=CH-CH_2Cl$ forms an allyl carbocation $(CH_2=CH-CH_2^+)$,which is resonance-stabilized. $(C)$ $(CH_3)_3C-Cl$ forms a tertiary carbocation $((CH_3)_3C^+)$,which is stabilized by the inductive effect $(+I)$ of three methyl groups. $(D)$ $CH_3-CH=CH-Cl$ would form a vinylic carbocation $(CH_3-CH=CH^+)$. $A$ positive charge on a carbon atom involved in a double bond is highly unstable due to the high electronegativity of $sp$-hybridized carbon. Therefore,$CH_3-CH=CH-Cl$ does not undergo hydrolysis by the $S_{N}1$ mechanism.

The organic halide,which does not undergo hydrolysis by $S_{N}1$ mechanism is

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