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KCET2015ChemistryAlcohols Phenols and Ethers

Arrange the following compounds in the increasing order of their acidic strength : i. m-nitrophenol ii. m-cresol iii. phenol iv. m-chlorophenol

Options

  1. Aiii ( < ii < i < iv )
  2. Bii ( < ) iv ( < iii < i )
  3. C( ii < iii < iv < i )
  4. Dii ( < iii < i < iv )

Correct answer

C. ( ii < iii < iv < i )

Step-by-step solution

Nitro group has both ( -R ) effect and ( -1 ) effect; but ( -R ) effect predominates. Due to stronger electron withdrawing nature of ( NO ₂ ) group, phenoxide ion is stabilized. Hence, m-nitrophenol is more acidic than phenol. Methyl group destabilizes the phenoxide ion by ( +I ) effect and hyperconjugation. Hence m-cresol is weaker acid than phenol. Chlorine have both +R and ( -1 ) effect but ( -1 ) effect predominates Hence m-chlorophenol is more acidic than phenol. ( -R ) effect of nitro group is stronger than (

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