Effect of the - NO₂ group on other nuclear substituents

         (a) Effect on nuclear halogen : The nuclear halogen is ordinarily inert, but if it carries one or more electron-withdrawing groups (like - NO₂) in o- or p-position, the halogen atom becomes active for nucleophilic substitutions and hence can be easily replaced by nucleophiles (KOH, NH₃, NaOC₂H₅).

         (b) Effect on phenolic -OH group : The acidity of the phenolic hydroxyl group is markedly increased by the presence of - NO₂ group in o- and p-position.

         The decreasing order of the acidity of nitrophenols follows following order

         Increased acidity of o- and p-nitrophenols is because of the fact that the presence of electron-withdrawing - NO₂ group in o-and p-position (s) to phenolic -OH group stabilises the phenoxide ions (recall that acidic nature of phenols is explained by resonance stabilisation of the phenoxide ion) to a greater extent.

    Due to increased acidity of nitrophenols, the latter react with phosphorus pentachloride to give good yields of the corresponding chloro derivative, while phenol itself when treated with PCl₅ gives poor yield of chlorobenzene.

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