Emmett, a sophomore chemistry major, was trying to separate an unknown mixture. His instructor told him that there was a carboxylic acid, phenol, and amine present in the mixture. He dissolved 3 g of the unknown in 10 ml of t-butyl methyl ether. He then added 10 ml of 3M sodium hydroxide to the mixture. He used a separatory funnel to separate the layers and collected the aqueous layer in an Erlenmeyer flask labeled fraction 1. Then he added 10 ml of 1.5M sodium bicarbonate to the remaining ether. He separated the layers, and collected the aqueous layer in an Erlenmeyer flask labeled fraction 2. Finally he added 10 ml of 1.5 M hydrochloric acid to the ether, and separated the aqueous later in an Erlenmeyer flask labeled fraction 3. Emmett neutralized the respective fractions. He obtained precipitate in fraction 1, and fraction 3. He ran an IR of the solid obtained in fraction 1 and saw a broad absorption at 3500-3300 cm-1 and a sharp absorption at 1710 cm-1. Fraction 3 showed strong absorptions at 2900 cm-1. Why did he not obtain any solid in fraction 2? What do you supposed the solid was in fraction 1 and fractions 3? How could he determine if the solid from fraction 2 is a pure solid?
Emmett, a sophomore chemistry major, was trying to separate an unknown mixture. His instructor told him that there was a carboxylic acid, phenol, and
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