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NEET CHEMISTRYMedium

The most acidic compound among the following is:

A

o-Cresol

B

Phenol

C

p-Nitrophenol

D

2,4,6-Trinitrophenol

Step-by-Step Solution

The acidity of phenols is determined by 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) exert electron-withdrawing inductive (I-I) and resonance (R-R) effects . These effects disperse the negative charge on the oxygen of the phenoxide ion, stabilising it and thus increasing the acidity of the parent phenol.
  2. Electron Donating Groups (EDG): Alkyl groups like methyl (CH3-CH_3) exert an electron-releasing inductive effect (+I+I) , which intensifies the negative charge on the phenoxide ion, destabilising it and decreasing acidity.
  3. Comparison:
  • o-Cresol: Contains a methyl group (+I+I effect), making it less acidic than phenol.
  • Phenol: Standard reference.
  • p-Nitrophenol: Contains one NO2-NO_2 group, making it more acidic than phenol.
  • 2,4,6-Trinitrophenol (Picric Acid): Contains three strong electron-withdrawing NO2-NO_2 groups at ortho and para positions. The cumulative I-I and R-R effects provide maximum stabilisation to the phenoxide ion, making it the most acidic compound among the options.
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