enter image description here

1) What could be the most plausible explanation to the very low percentage of the nitro group attacking the site between bromine and chlorine? - is it solely because of steric hinderence - or is it because of the inefficient pi-electron overlaps by the larger chlorine and bromine atoms suppressing resonance in the region between them - or is it inductive effect

2) why is the first product (given above) more formed than the second. Is it because of the more electronegativity of Cl over Br which could lessen the stability of compound 2 by negative induction effect( which destabilised nitro group which itself is electron withdrawing).

  • $\begingroup$ Inductive effects scale down with increased distance from the electronegative atom. What's more acidic? trifluoroacetic acid or 3,3,3-trifluoropronanoic acid? $\endgroup$ – Zhe Mar 8 '19 at 15:54
  • $\begingroup$ Zhe, yeah I got that point fine but my doubt is if it even the same for aromatic compounds? Or do the compounds by any chance distribute the positive charge over the ring to maintain homogeneousity? $\endgroup$ – Kai Hiwatari Mar 8 '19 at 16:37
  • $\begingroup$ Positive charge in what sense? The localization of charge into the $\pi$ system is probably fairly even, but the inductive effect is much stronger at the 2-position than the 4-position, relative to the halide. $\endgroup$ – Zhe Mar 8 '19 at 18:13
  • $\begingroup$ Ok so is induction the sole reason for the cause? Is induction that strong and effective to cause only 1% of the last product? Thank you. $\endgroup$ – Kai Hiwatari Mar 8 '19 at 18:23
  • $\begingroup$ No, that's probably also steric. But steric effects should be similar between products 1 and 2. $\endgroup$ – Zhe Mar 8 '19 at 18:27

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.