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why cant acetanilide be initially dissolved in HNO3 in the synthesis of p-nitroacetanilide

why cant acetanilide be initially dissolved in HNO3 in the synthesis of p-nitroacetanilide

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Answer #1

The addition of nitric acid is exothermic. Therefore the mixture would get too hot exceeding the temperature range suitable for the nitration. To avoid this, the addition of HNO3 acid should be done very slowly, dropwisely.

Cold temperatures were used to slowdown the reaction rate and help to avoid over nitration.

Glacial acetic acid is used because it is a polar solvent capable of dissolving acetanilide and the acetate ion is a poor nucleophile, so no substitution is possible.

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