Q61Short answer
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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This reaction is an example of electrophilic aromatic substitution. In alkaline medium, phenol generates phenoxide ion which is more electron rich than phenol and hence more reactive for electrophilic attack. The electrophile in this reaction is aryldiazonium cation. Stronger the electrophile faster is the reaction. p-Nitrophenyldiazonium cation is a stronger electrophile than p-toluene diazonium cation. Therefore, it couples preferentially with phenol. 197 Amines