The major product of the following reaction i | vedclass

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Question

(B) The reaction is the electrophilic addition of $2HBr$ to $1-$methyl$-4-$nitrocyclohexa$-1,4-$diene. $(1)$ The $NO_2$ group is strongly electron-wit

Vedclass · Accepted Answer

$1,3-$dibromo$-1-$methyl$-4-$nitrocyclohexane

Vedclass · Answer

(B) The reaction is the electrophilic addition of $2HBr$ to $1-$methyl$-4-$nitrocyclohexa$-1,4-$diene. $(1)$ The $NO_2$ group is strongly electron-withdrawing, making the adjacent double bond electron-deficient and less reactive toward electrophiles. $(2)$ The double bond at the $C1$ position (with the methyl group) is more electron-rich. Protonation occurs at $C2$ to form a tertiary carbocation at $C1$. $(3)$ $Br^-$ attacks the $C1$ carbocation to form $1-$bromo$-1-$methyl$-4-$nitrocyclohex$-4-$ene. $(4)$ The second $HBr$ adds to the remaining double bond. According to Markovnikov's rule, $H^+$ adds to $C5$ (to form a more stable carbocation at $C4$ adjacent to the $NO_2$ group is incorrect; actually, the $NO_2$ group destabilizes the carbocation at $C4$, so the $H^+$ adds to $C4$ and $Br^-$ adds to $C3$). $(5)$ The final product is $1,3-$dibromo$-1-$methyl$-4-$nitrocyclohexane.

The major product of the following reaction is:

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