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(C) For $SN^1$ and $SN^2$ mechanisms,the reactivity depends on the stability of the carbocation (for $SN^1$) and steric hindrance/leaving group abilit

Vedclass · Accepted Answer

$Benzyl chloride > Chlorobenzene$

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(C) For $SN^1$ and $SN^2$ mechanisms,the reactivity depends on the stability of the carbocation (for $SN^1$) and steric hindrance/leaving group ability (for $SN^2$).$A$: $sec-butyl chloride$ is less reactive than $sec-butyl bromide$ because $Br^-$ is a better leaving group than $Cl^-$.$B$: $CH_2=CHCl$ (vinyl chloride) is very unreactive due to partial double bond character,while $CH_3CH_2Cl$ is a primary alkyl halide. Thus,$CH_3CH_2Cl > CH_2=CHCl$.$C$: $Benzyl chloride$ $(C_6H_5CH_2Cl)$ is highly reactive in both $SN^1$ (due to resonance-stabilized benzyl carbocation) and $SN^2$ (due to resonance stabilization of the transition state). $Chlorobenzene$ is extremely unreactive in both mechanisms due to the partial double bond character of the $C-Cl$ bond and the instability of the phenyl cation. Therefore,$Benzyl chloride > Chlorobenzene$ is correct.$D$: $CH_2=CH-CH_2Cl$ (allyl chloride) is more reactive than $CH_2=CHCl$ due to resonance stabilization of the allyl carbocation and less steric hindrance. Thus,$CH_2=CH-CH_2Cl > CH_2=CHCl$.

Which of the following represents the correct reactivity order for both $SN^1$ and $SN^2$ mechanisms?

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