Question

2. This extraction involves acid/base chemistry. Some amines (like carboxylic acids) are not very water soluble, but that property can change because of their basicity (or acidity). Which of the following could be added to an amine in order to make it more water soluble? (NOTE: look up relevant pKa and/or pKb values)

NaOEt

H2O

NaHSO4

H2

3. Benzoic acid is dissolved in a solution of sodium hydroxide. Half of the solution is added to a separatory funnel and combined with diethyl ether. The funnel is shaken vigorously. The ether now contains : a) sodium benzoate b) benzoic acid c) nothing d) sodium hydroxide

Answer 1

2. When amines get converted into their quarternary ammonium salts then they will become more water soluble (salts like chlorides, bromides, nitrates, sulfates, bisulfates). NaHSO₄ converts amine to ammonium bisulfate and this salt is more water soluble.

Answer: NaHSO₄

3. Benzoic acid is a weak acid and soluble in non-polar organic solvents like acetone, benzene, CCl₄, CHCl₃, alcohol, ethyl ether, hexane, phenyls, liquid ammonia, but its sodium salt sodium benzoate is more soluble in water. Hence ether contains benzoic acid only.

Answer: b) benzoic acid

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