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NEET CHEMISTRYMedium

Among the following four compounds: (a) Phenol (b) Methyl phenol (c) meta-nitrophenol (d) para-nitrophenol

The acidity order is:

A

c > d > a > b

B

a > d > c > b

C

b > a > c > d

D

d > c > a > b

Step-by-Step Solution

The acidity of phenols is determined by the stability of the phenoxide ion formed after losing a proton.

  1. Electron-Withdrawing Groups (EWG): Groups like NO2-NO_2 withdraw electrons, dispersing the negative charge on the oxygen and stabilizing the phenoxide ion, thus increasing acidity.
  • para-nitrophenol (d): The NO2-NO_2 group exerts both a strong electron-withdrawing resonance effect (R-R) and an inductive effect (I-I) at the para position. This makes it the most acidic.
  • meta-nitrophenol (c): The NO2-NO_2 group at the meta position exerts only the electron-withdrawing inductive effect (I-I). The resonance effect does not operate at the meta position. Therefore, it is less acidic than the para isomer but more acidic than phenol.
  1. Standard: Phenol (a) has no substituents and serves as the reference.
  2. Electron-Donating Groups (EDG): Groups like methyl (CH3-CH_3) release electrons (via +I+I effect and hyperconjugation), intensifying the negative charge on the oxygen and destabilizing the phenoxide ion, thus decreasing acidity.
  • Methyl phenol (b): Due to the electron-donating nature of the methyl group, it is less acidic than phenol.

Conclusion: The order of acidity is d > c > a > b.

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