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Question: Answered & Verified by Expert
In the following compounds

The order of acidity is
ChemistryGeneral Organic ChemistryNEET
Options:
  • A III > IV > I > II
  • B I > IV > III > II
  • C II > I > III > IV
  • D IV > III > I > II
Solution:
2417 Upvotes Verified Answer
The correct answer is: IV > III > I > II
-NO2 is an electron attracting group whereas -CH3 is an electron releasing group. An electron attracting substituent tends to disperse the negative charge of phenoxide ion and thus makes it more stable. This in turn increases the acidity of phenol. The substituent in Para-position is more effective than in meta-position as the former involves a resonating structure bearing negative charge on the carbon attached to electron with drawing substituent.
An electron releasing substituent tends to increase the negative charge of peroxide ion and thus makes it more unstable. This, in turn, decreases the acid strength of phenol.

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