BRAINCAKEWhy Phenol is More Reactive than Benzene
Phenol, C6H5OH, reacts with bromine far more readily than benzene does. Benzene needs pure liquid bromine and a halogen carrier such as FeBr3, but phenol decolourises bromine water at room temperature with no catalyst at all.
The difference comes from the oxygen atom of the OH group. One of the lone pairs on the oxygen overlaps with the delocalised π electrons of the ring, so this lone pair becomes partly delocalised into the ring. This increases the electron density of the ring, and the increase is greatest at the 2, 4 and 6 positions.
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More in Arenes
- Combustion of Benzene
- Electrophilic Substitution
- Bromination of Benzene
- Nitration of Benzene
- Friedel-Crafts Alkylation
- Friedel-Crafts Acylation
- Phenol
- Reaction of Phenol with Bromine Water
All 13 lessons in Arenes · All Edexcel A-level Chemistry topics