Which among the following substituent groups decreases the acidic strength of aromatic carboxylic acid?

Which among the following substituent groups decreases the acidic strength of aromatic carboxylic acid?
  1. $-\mathrm{NH}_{2}$
  2. $-\mathrm{CN}$
  3. $-\mathrm{Cl}$
  4. $-\mathrm{N} \mathrm{O}_{2}$

Solution

$-\mathrm{NH}_{2}$ is electron donating group which activate the benzene ring to electrophilic attack and make aromatic carboxylic acids less acidic. While $-\mathrm{Cl},-\mathrm{CN}$ and $-\mathrm{NO}_{2}$ are electron withdrawing groups which increases the acidity of aromatic carboxylic acids.

Asked in: MHT CET 2020 (12 Oct Shift 2)

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