Which of the following is most reactive for S | vedclass

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(A) The reactivity of a compound towards $SN^1$ reaction depends on the stability of the carbocation intermediate formed after the departure of the le

Vedclass · Accepted Answer

p-Methoxybenzyl chloride

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(A) The reactivity of a compound towards $SN^1$ reaction depends on the stability of the carbocation intermediate formed after the departure of the leaving group (chloride ion).In these cases,the carbocation formed is a substituted benzyl carbocation $(Ar-CH_2^+)$.The stability of the benzyl carbocation is increased by electron-donating groups $(EDG)$ and decreased by electron-withdrawing groups $(EWG)$ attached to the benzene ring.$1$. $p$-Methoxybenzyl chloride: The $-OCH_3$ group is a strong electron-donating group by resonance ($+R$ effect),which significantly stabilizes the carbocation.$2$. $p$-Nitrobenzyl chloride: The $-NO_2$ group is a strong electron-withdrawing group ($-R$ and $-I$ effect),which destabilizes the carbocation.$3$. $p$-Methylbenzyl chloride: The $-CH_3$ group is a weak electron-donating group by hyperconjugation ($+H$ effect).$4$. $p$-Chlorobenzyl chloride: The $-Cl$ group is electron-withdrawing by induction ($-I$ effect),although it can donate electrons by resonance ($+R$ effect),the net effect is electron-withdrawing.Since the $-OCH_3$ group provides the greatest stabilization to the carbocation through its strong $+R$ effect,$p$-methoxybenzyl chloride is the most reactive towards $SN^1$.

Which of the following is most reactive for $SN^1$ reaction?

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