Question Details

Phenol is brominated in solvent CS2 at low temperature. The product formed are:


Options

A

Monobromophenols

B

Dibromophenols

C

Tribromophenols


D

Tribromobenzene


Show Answer

Correct Answer :

Option B

Dibromophenols

Solution :

The correct option is Dibromophenols.

Phenol undergoes electrophilic aromatic substitution when treated with halogenating agents. The hydroxyl group (-OH) attached to the benzene ring is highly activating and ortho/para-directing due to resonance activation.

When bromination of phenol is carried out in a non-polar or low-polarity solvent like carbon disulfide (CS2) at low temperatures (around 273 K), the reaction conditions are mild. Under these conditions, the ionization of phenol to the highly reactive phenoxide ion is suppressed. Consequently, the rate of substitution is controlled, leading to moderate bromination where isomeric products are formed. This controlled reaction yields ortho- and para- isomers, and can selectively form dibromophenols depending on the reaction parameters, unlike in aqueous media where rapid tri-substitution occurs to form 2,4,6-tribromophenol.

The overall reaction can be represented as follows:

C 6 H 5 O H + B r 2 C S 2 , low temp Dibromophenols + H B r

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