Benzoic acid is soluble in diethyl ether but not water, however, benzoic acid is extracted from diethyl ether with aqueous sodium hydroxide.

a. Complete the acid-base reaction below by writing the products of the reaction.

b. In the reaction of Part a, label the acid, the base, the conjugate acid, the conjugate base.

c. Indicate the solubility of benzoic acid and its conjugate base in diethyl ether and in water.

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Amarildo KociajLv10

18 Jan 2021

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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 (C6H5âCOOH) 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!

To separate a mixture of benzoic acid and fluorene, we are going to use an acid-base extraction technique. Most carboxylic acids are insoluble or slightly soluble in water, but they are highly soluble in dilute aqueous sodium hydroxide because the organic acid reacts with the base and produces carboxylate ions, a polar species. In a mixture of a carboxylic acid and an organic compound, the acid may be selectively removed from an organic solvent by extracting with a dilute NaOH solution. After separating the organic and aqueous layers, the carboxylic acid may be recovered from the aqueous solution by adding HCl, which causes precipitation of the carboxylic acid. Draw two structures below.To separate a mixture of benzoic acid and fluorene