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NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

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.

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Alcohols, Phenols and Ethers. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYAlcohols, Phenols and Ethersfollowingcompoundsphenolmethylphenol

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