Chemistry students were given the task of synthesizing p-Nitroacetanilide given the
-glacial acetic acid
The reaction mixture was poured into a beaker containing ice water allowing a solid precipitate to form. This solid precipitate contains a mixture of p-Nitroacetanilide and o-Nitroacetanilide.
The solid precipitate was collected into a buchner funnel and this solid precipitate was washed with 150 mL portions of cold water. Each 150 mL portion of "acidic filtrate" was collected into a beaker. This beaker of "acidic filtrate" contains a majority of the "ortho" product o-Nitroacetanilide.
Prior to recrystallization of o-Nitroacetanilide in the beaker labeled "acidic filtrate" the Chemistry students accidentally neutralized this solution with solid sodium bicarbonate believing the solution was supposed to be disposed in organic waste.
How can the Chemistry students can still obtain the ortho product from the beaker labeled "acidic filtrate" after the solution had been neutralized with solid sodium bicarbonate?
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