Why Bromobenzene don't react with aq.NaOH ?

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Solution

At normal condition bromobenzene does not react with aq. NaOH. As haloarenes are less prone to nucleophilic substitution reaction compared to haloalkenes. This reaction is used to distinguish between ethyl bromide and bromobenzene. Ethyl bromide undergoes substitution to produce ethyl alcohol and NaBr. Treatment with acidified silver nitrate gives light yellow ppt of AgBr. But bromobenzene does not undergo hydrolysis at these condition and thus no ppt of AgBr can be seen.

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