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Alcohols, Phenols and Ethers
Question
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Among the following four compounds

A) Phenol 
B) Methyl Phenol
C) meta - nitrophenol
D) para-nitrophenol

the acidity order is

  • D > C > A > B

  • C > D > A> B

  • A > D > C > B

  • B > A > C> D 

Answer

A.

D > C > A > B

An electron withdrawing group (-I showing group like -NO2, -CN) stabilises the phenoxide ion, thus when present, increases the acidity of phenol. On the other hand, the electron releasing groups (+I showing group like -CH3, -C2H5), when present, decrease the acidity of phenol by destabilising phenoxide ion. Hence, the correct order of acidity of given compound is
p-nitrophenol > m-nitrophenol > phenol > methyl phenol

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