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Question
A solution contains 1 g mol. each of p-toluene diazonium chloride and p-nitrophenyl diazonium chloride. To this 1 g mol. of alkaline solution of phenol is added. Predict the major product. Explain your answer.
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Solution
This reaction is an example of electrophilic aromatic substitution. In alkaline medium, phenol forms phenoxide ion which is more electron-rich than phenol and hence more reactive for electrophilic attack. The electrophile in this reaction is aryl diazonium cation. p-Nitrophenyldiazonium cation is a stronger electrophile than p-toluene diazonium cation. Therefore, it couples preferentially with phenol.
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