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

$\therefore$ 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)