Which one of the following functional groups is not meta directing?

Which one of the following functional groups is not meta directing?
  1. $-\mathrm{COOH}$
  2. $-\mathrm{NO}_2$
  3. $-\mathrm{CHO}$
  4. $-\mathrm{OCH}_3$

Solution

Key Idea The group which contain double bond in its structure and have more electronegative element bonded with the atom (which is bonded with the C-atom of benzene ring) gives $m$-directing products and those do not have double bond and have lone pair electron over the atom, (which is bonded with the benzene ring) do not give m-directing product (they give o and $p$-products). (a) - $\mathrm{COOH}$ group, contains double bond in its structure and - C-atom, which is bonded with the ring has more electronegative oxygen atom bonded with it. i.e.
$\therefore$ It gives $m$-directing product. (b) $-\mathrm{NO}_2$ group, contains double bond in its structure and $\mathrm{N}$-atom, which is bonded with the ring has more electronegative oxygen atom bonded with it. i.e.
$\therefore$ It gives $m$-directing product. (c) - CHO group also contains double bond in its structure and $\mathrm{C}$-atom, which is bonded with the ring has more electronegative oxygen atom bonded with it. i.e.
$\therefore$ It gives $m$-directing product. (d) $-\mathrm{O}-\mathrm{CH}_3$ group, has no double bond in its structure and $\mathrm{O}$-atom, which is bonded with the ring has less electronegative $\mathrm{C}$-atom, bonded with it. i.e.
Thus, it does not give $m$-directing product. Hence, option (d) is the correct.

Asked in: AP EAMCET 2019 (21 Apr Shift 1)

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