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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 $\mathrm{AlBr}_{3}$ needed

M2: lone pair (of $\mathrm{e}^{-}$ )/p-orbital on oxygen

AND overlap / delocalised with ring / $\pi$ system

M3: electron density in ring increases / ring becomes more electron rich (and attracts electrophiles)

M4: (phenol is more reactive so) polarises $\mathrm{Br}_{2} /$ bromine / electrophiles more

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CAIE A-Level Chemistry A2 32.2.5 Phenol Nitration and Bromination Conditions Topic Practice

Question 1