What would happen if (E)-4-Phenyl-3-buten-2-one, shown above is nitrated, and is this compound more or less reactive than benzene?
My Attempt: By drawing the resonance structures of the above compound, I noted that the functional group withdrew electron density from the benzene ring. This means that this compound would be less reactive than benzene; my book agrees with me on that.
However, I stated that the nitro group would be added to the ortho or para positions, due to the fact that the sigma complex created is more stable due to the resonating effects of the double bond in the functional group. On the other hand, nitrification at the meta position would result in only three resonance structures in the sigma complex, resulting in a less stable compound. However, my book states that because the functional group is a deactivating group, it is a meta-director, without any further explanation. While I understand this rule is true in the general case, why does this rule still apply in the above compound, rendering my answer wrong?