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NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

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.

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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