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

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

AP EAMCETAP EAMCET 2019

Solution:

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) $- COOH$ 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.

$\left[ - \underset{\overset{||}{O}}{C} - OH \right]$

$\therefore $ It gives $m$- directing product.

(b) $- NO _{2}$ group, contains double bond in its structure and $N$ -atom, which is bonded with the ring has more electronegative oxygen atom bonded with it. i.e.

image

$\therefore $ It gives $m$ -directing product.

(c)$ - CHO$ group also 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.

$\left[ - \underset{\overset{||}{O}}{C} - OH\right]$

$\therefore $ It gives $m$ -directing product.

(d) $- O - CH _{3}$ group, has no double bond in its structure and $O$-atom, which is bonded with the ring has less electronegative $C$ -atom, bonded with it. i.e.

image

Thus, it does not give $m$ - directing product.