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13 Dec 2019

Organic Chemistry: Separating Acids and Neutral Compounds by Solvent Extraction

Reagents and Solvents Used

Acetanilide/p-Toluic Acid mixture, diethyl ether, 3M hydrochloric acid, 0.5M sodium hydroxide, sodium sulfate, anhydrous, water-distilled or deionized

PURPOSE OF THE EXPERIMENT: Use solvent extraction techniques to separate a mixture consisting of a carboxylic acid and a neutral compound.

Questions:

1. What product would you obtain if you evaporated the water from the NaOH layer prior to acidifying the layer?

2. Suppose that you used dichloromethane instead of diethyl ether as the nonpolar solvent in this experiment. What changes in the procedure would you make in view of the fact that dichloromethane is more dense than water?

3. Benzoic acid (C6H5—COOH) is a weak acid and naphthalene is neutral, neither acidic or basic. Prepare a flowchart for the separation and recovery of benzoic acid and naphthalene.

Benzoic Acid: solubility in water: poor ; solubility in ether: good

Naphthalene: solubility in water: poor ; solubility in ether: good

Thank You In Advance!

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Related questions

You have dissolved 2 g of a mixture of benzoic acid and naphthalene in 30 ml of diethyl ether and started the extraction procedure.

Match the question with an appropriate answer from the drop-box. Before answering the questions below get the data about density of the solvents you use.

You transferred the solution of benzoic acid and naphthalene in diethyl ether to the separatory funnel and added on top15 ml of 2.5 M NaOH solution. Where you would find the aqueous solution, at the top or at the bottom of the separatory funnel?

You transferred prepared solution of benzoic acid and naphthalene in diethyl ether to the separatory funnel and added on top15 ml of 2.5 M NaOH solution and you shook the separatory funnel. Where you would find the aqueous solution, at the top or at the bottom of the separatory funnel?

After completing the extraction the procedure in the textbook recommends you to transfer the organic solution into a clean Erlenmeyer flask. What is the composition of organic solution?

After completing the extraction the procedure in the textbook recommends you to transfer the aqueous layer into a clean Erlenmeyer flask. What is the composition of aqueous layer?

Possible answers for all above questions:

1.The aqueous layer is a solution of benzoic acid in water

2. The organic solution is a solution of sodium benxoate in 2.5M aqueous solution

3. The aqueous layer is a solution of sodium benzoate and excess of sodium hydroxide in water

4. Aqueous solution will be found at the bottom of the separatory funnel

5. The organic solution is a solution of aphthalene in diethyl ether

6.The aqueous layer is a solution of sodium benzoate in water

7.The organic solution is a solution of benzoic acid in diethyl ether

8. The organic solution is a solution of naphthalene an benzoic acid in diethyl ether

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