DAT Genius Orgo Question

[drsoni]

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Hey guys,
I had a questions about a DAT genius orgo problem (pic attached). Why would option A be considered wrong? Can't be attach the nitro group on the ortho position instead of the para position first, and then attach Cl to meta position to the nitro group?

 

[Syxx]

You could and would likely get a small amount of 2-nitroaniline but the 4-nitroaniline will be the major product due to less steric hindrance for the approaching nitro group.

Not really a great question though since in those conditions you would form the meta product of the nitroaniline almost as much as para. This happens because aniline will be protonated to form anililium ion which is strongly meta directing.