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Q. Which of the following group(s) is/are $m$-directing?

Organic Chemistry – Some Basic Principles and Techniques

Solution:

Although halogens are deactivating by -Ieffect, they are $o$ - and $p$-directing due to $+ R$ effect. $Ph -$ $CH = CH _2$ due to electromeric effect, donates $\pi e^{-}$s to the benzene and stabilizes intermediate $\sigma$ -
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Also, $(- CHO )$ and $(- COOH )$ do not have LP $\bar{e}^{\prime}$ s and thus withdraw $\bar{e}^{\prime}$ s from benzene ring and deactivate the ring at $o$ - and $p$-position. Thus, they are $m$ directing