Which of the following compounds gives the sa | vedclass

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Question

(A) For a compound to give the same product in both $S_N1$ and $S_N2$ reactions,the carbocation formed in $S_N1$ must be symmetric or lead to the same

Vedclass · Accepted Answer

$3-$chlorocyclohex$-1-$ene

Vedclass · Answer

(A) For a compound to give the same product in both $S_N1$ and $S_N2$ reactions,the carbocation formed in $S_N1$ must be symmetric or lead to the same product as the $S_N2$ inversion.In $3$-chlorocyclohex-$1$-ene,the $S_N1$ mechanism involves the formation of a resonance-stabilized allylic carbocation. The positive charge can be delocalized between $C_1$ and $C_3$ positions. Nucleophilic attack can occur at either position,leading to a mixture of products.However,in $3$-chlorocyclohex-$1$-ene,the structure is such that the allylic carbocation formed is symmetric with respect to the double bond position,or the substitution leads to the same product due to the resonance stabilization of the allylic cation. Specifically,the $3$-chlorocyclohex-$1$-ene molecule allows for the nucleophile to attack the allylic position,and due to the symmetry of the resonance structures,the product is the same.

Which of the following compounds gives the same $S_N1$ and $S_N2$ product?

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