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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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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 aryl diazonium cation. Stronger the electrophile faster is the reaction. p-Nitrophenyl diazonium cation is a stronger electrophile than p-toluene diazonium cation. Therefore, it couples preferentially with phenol.
Correct Option is : (D)
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 aryl diazonium cation. Stronger the electrophile faster is the reaction. p-Nitrophenyl diazonium cation is a stronger electrophile than p-toluene diazonium cation. Therefore, it couples preferentially with phenol.
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 aryl diazonium cation. Stronger the electrophile faster is the reaction. p-Nitrophenyl diazonium cation is a stronger electrophile than p-toluene diazonium cation. Therefore, it couples preferentially with phenol.
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