The electrophile,E^{+},attacks the benzene ri | vedclass

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Question

(C) In nitrobenzene,the $-NO_2$ group is a strong electron-withdrawing group ($-I$ and $-M$ effect). When an electrophile $E^{+}$ attacks the benzene

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(C) In nitrobenzene,the $-NO_2$ group is a strong electron-withdrawing group ($-I$ and $-M$ effect). When an electrophile $E^{+}$ attacks the benzene ring,the positive charge in the $\sigma$-complex is delocalized over the ring. For ortho and para attacks,one of the resonance structures places the positive charge directly on the carbon atom attached to the electron-withdrawing $-NO_2$ group,which is highly destabilizing. For meta attack,the positive charge is never placed on the carbon atom attached to the $-NO_2$ group. Therefore,the $\sigma$-complex formed by meta attack is the most stable (lowest energy) among the three,which explains why the $-NO_2$ group is meta-directing in electrophilic substitution reactions $(ESR)$.

The electrophile,$E^{+}$,attacks the benzene ring to generate the intermediate $\sigma$-complex. Which $\sigma$-complex is of lowest energy?

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