DESTROYER orgo #21...error?

[funkyCHICKEN]

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#21. Answer says that the groups attached on b c and e are e withdrawing...does it mean e donating? (according to chad they are donating!!! 🙁

 

[J777]

That is a good point you bring up. Those certainly are electron donating groups in electrophilic aromatic substitution rxns (b and c), However, in ranking basicity for b and c, the key here is that the lp electrons on the nitrogen can be delocalized on the benzene ring, which stabilizes the molecule (I.e. it would be less likely to accept a proton in an acid base rxn). Further, the electrons in option c can be delocalized to the carbonyl group. In the case of e, the nitro group is very electron withdrawing (in the traditional sense). When you have an electron withdrawing group on an aniline, it further decreases the basicity of the molecule

 

[cmF]

#21. Answer says that the groups attached on b c and e are e withdrawing...does it mean e donating? (according to chad they are donating!!! 🙁

What version of DAT Destroyer do you have? I don't see that question in my 2012 version. Also, it's best if you post a picture of the question in question because you'll most likely get more answers that way.