Question

phenol gives 2,4,6-tribromophenol oN bromination with bromine water. explain. ​

Answer 1

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The reaction of phenol with bromine is known as bromination of phenol. Solvent has great influence on the reaction.In different solvents, different products are obtained.The action of bromine on phenol can be explained as.

Reaction with bromine in water:—-
see 1st attachment

Phenol reacts with bromine water to give 2,4,6-tribromophenol.

In water, ionisation is facilitated.Phenol gets ionised to form phenoxide ion, which is even better ortho-para directing.Bromine also gets ionised to a larger extent to form a large number of bromonium ions.And Bromine ions are highly stabilized in ionic solvents.So the formation of strong o/p directing group and stabilization of Br+ enhances the formation of tribromophenol.

Reaction with bromine in CS₂:—-
see 2nd attachment

Phenol reacts with bromine in a presence of Carbon disulphide to form a mixture of o-bromophenol and p-bromophenol.Among which p-bromophenol predominates.In CS₂ ionisation is not facilitated that much.As it is a non-polar solvent it doesn't the Br+ on.Also -OH group is moderately o/p directing. So as usual Para product is more formed.


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Answer 2

In water ionisation is fascilitated.Phenol get ionised to form phenoxide ion,which is even better ortho-para directing.Bromine also get ionised to larger extent to form large number of bromonium ions.