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NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

The most acidic compound among the following is:

A

Phenol

B

2,4,6-Trinitrophenol

C

p-Nitrophenol

D

m-Nitrophenol

Step-by-Step Solution

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

  1. Resonance and Inductive Effects: Electron-withdrawing groups (EWG) like nitro (NO2-NO_2) stabilize the phenoxide ion through resonance (R-R effect) and inductive (I-I effect) mechanisms, dispersing the negative charge and increasing acidity .
  2. Number of Substituents: The more electron-withdrawing groups present, the greater the stabilization of the phenoxide ion.
  3. Comparison:
  • Phenol: No substituents.
  • p-Nitrophenol: One NO2-NO_2 group (stabilizes via I-I and R-R).
  • m-Nitrophenol: One NO2-NO_2 group (stabilizes via I-I only, as resonance effect does not operate effectively from meta position).
  • 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 (even more acidic than many carboxylic acids).

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.

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