CAIE A-Level Chemistry 32.2.5 Nitration and Bromination of Phenol
Practise explaining why phenol undergoes nitration and bromination under milder conditions than benzene.
- Syllabus
- 2028–2030
- Course
- Chemistry 9701
- Level
- A2
Practise explaining why phenol undergoes nitration and bromination under milder conditions than benzene.
Cumene is an aromatic hydrocarbon used in the synthesis of other useful chemicals.

cumene
Fig. 5.4 shows two reactions of phenol.

Fig. 5.4
State the conditions for the bromination of phenol in reaction 2 .
Explain why these conditions are different from those for the bromination of benzene. conditions
explanation
M1: conditions for phenol =
- aqueous / aq
- bromine water
- no AlBr3 needed
M2: lone pair (of e−)/p-orbital on oxygen
AND overlap / delocalised with ring / π system
M3: electron density in ring increases / ring becomes more electron rich (and attracts electrophiles)
M4: (phenol is more reactive so) polarises Br2/ bromine / electrophiles more