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Nitration of Phenol produces only 2-nitrophenol & 4-nitrophenol?! Why?! Watch

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    Why Nitration of Phenol produces only 2-nitrophenol & 4-nitrophenol?!
    Is it not possible for 3-nitrophenol to occur too?
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    You would get 3-nitrophenol but only a very very low yield compared to the 2 and 4 isomers. This is mainly due to the mesomeric effect:



    The delocalisation of oxygen's lone pair into the aromatic system increases electron density at the 2 and 4 positions. These positions therefore are much better at attacking the nitronium ion than the 3 position is.
 
 
 
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