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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?

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    $\begingroup$ I don't know why you deleted it, but your book is wrong on this count. Nitration of your compound yields the ortho and para isomers, for the reasons you mentioned. Chem. Ber. 1882, 15, 2861; ibid 1883, 16, 2205; J. Chem. Soc. 1933, 344 $\endgroup$ – orthocresol Aug 1 '17 at 6:33
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    $\begingroup$ @orthocresol Thank you for pointing this out; I thought that I was actually wrong after reconsidering the problem, due to the fact that the additional resonance structure would be very minimally affecting the stability due to its positive charge on both the beta and alpha carbon of the carbonyl group. Please repost the comment as an answer and I will accept it. $\endgroup$ – Teoc Aug 1 '17 at 18:09

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