why doesn't Br2 add ortho to the CHS in this molecule? Please click to view the molecule. Also, can you explain it? why the solutions manual says the Br is ortho to the N group? I would have thought sterics would inhibit that...
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2006-08-27 10:53:13 · 2 answers · asked by Anonymous in Science & Mathematics ➔ Chemistry
Groups with unshared pairs of electrons, such as the amino group of aniline, are strongly activating and ortho/para-directing.
When the electrophile attacks the ortho and para positions of aniline, the nitrogen atom can donate electron density to the pi system, giving four resonance structures (as opposed to three in the basic reaction). This substantially enhances the stability of the cationic intermediate. Compare this with the case when the electrophile attacks the meta position.
This is from wikipedia check the link for more info. Hope it helps.
2006-08-27 11:02:43 · answer #1 · answered by kano7_1985 4 · 0⤊ 0⤋
ok let's break this down.
you have a Me and a nitrogen
Me- meta director
N - ortho, para.
it adds there because that's the most energy efficient. it overrides steric, and with the hydrogen there there isn't much sterics to overcome. remember sterics isn't the be all end all, and is not the answer for everything
2006-08-27 11:52:48 · answer #2 · answered by shiara_blade 6 · 0⤊ 0⤋