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NEET CHEMISTRYMedium

Which one is the most acidic compound?

A

o-Cresol

B

Phenol

C

p-Nitrophenol

D

2,4,6-Trinitrophenol (Picric Acid)

Step-by-Step Solution

The acidity of phenols depends on the stability of the phenoxide ion formed after the loss of a proton.

  1. Electron Withdrawing Groups (EWG): Substituents like the nitro group (NO2-NO_2) are electron-withdrawing due to resonance (R-R) and inductive (I-I) effects . These groups disperse the negative charge on the phenoxide ion, thereby stabilizing it and increasing the acidic strength.
  2. Number and Position: The stabilizing effect is most pronounced when EWGs are at ortho and para positions. Greater the number of EWGs, higher is the acidity.
  3. Picric Acid: 2,4,6-Trinitrophenol contains three nitro groups at ortho and para positions. The combined strong electron-withdrawing influence makes it the most acidic among standard phenolic compounds, even stronger than some carboxylic acids.
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