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Here, I count the individual effects of the two oppositely directing groups. I assume that the deactivation of $\ce{NO_2}$ group at ortho and meta positions is higher. While bromination, I get the product as mentioned above. My query :

If OH group is more powerful than nitro group, then why doesn't bromination occur at ortho position on between and para position ?

If I apply the same logic in the following compounds' bromination, will the points marked red be the permissible position for substitution (separately) ?

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    $\begingroup$ With two oppositely directing groups, I'd expect a complete mess. $\endgroup$ – Ivan Neretin Aug 6 '18 at 15:39
  • $\begingroup$ @Ivan... I'm in a mess... I saw the first one in a website... Then I did the rest two myself. However, I didn't understand the symmetry in the third one... $\endgroup$ – Entrepreneur Aug 6 '18 at 15:42
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    $\begingroup$ What's to understand? One Cl directs with the same force as the other. $\endgroup$ – Ivan Neretin Aug 6 '18 at 15:47

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