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Alcohols, Phenols And Ethers

Question
CBSEENCH12008307

Write the resonance structures of phenol (which is similar to that of chlorobenzene) and explain why it does not form chlorobenzene on reaction with PCI5 Explain whether phenol can be dehydrated on heating with catalytic amounts of conc. H2SO4.

Solution
Resonance structures of phenol:

Due to resonance, carbon-oxygen bond develops a slight double bond character. Therefore, it is not easy to replace —OH in phenols by Cl.
No, phenols cannot be dehydrated on heating with small amount of conc. H2SO4. Instead, phenols with conc. H2SO4 undergoes sulphonation.