What happen when phenol reacts with conc.HNO3
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When phenol reacts with dilute nitric acid at room temperature, electrophilic substitution occurs to form a mixture of 2-nitrophenol and 4-nitrophenol.
This nitration occurs faster than the nitration of benzene because the ring is more electron dense in phenol as the lone pair of electrons in the 2pz orbital of the oxygen atom (of the OH functional group) are drawn into the ring, and become a part of the delocalised pi system. This increase in electron density makes the benzene ring in phenol a stronger nucleophile, which increases the rate of substitution by the powerful NO2+ electrophile formed from nitric acid.
This nitration occurs faster than the nitration of benzene because the ring is more electron dense in phenol as the lone pair of electrons in the 2pz orbital of the oxygen atom (of the OH functional group) are drawn into the ring, and become a part of the delocalised pi system. This increase in electron density makes the benzene ring in phenol a stronger nucleophile, which increases the rate of substitution by the powerful NO2+ electrophile formed from nitric acid.
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