Lab 2

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CHEM 282 Experiment #2: Separation of an Acid, a Base, and a Neutral Compound by Extraction Sophie Wolkoff (20107258) & Kaelen Partridge (20127197) TA: Bily Deng January 30, 2020
Experimental: Before the experiment, a flow chart was provided in the lab manual in step 1 which displayed each stage in the separation scheme in order to summarize the actions to separate a mixture into its constituents. Step 2 of the experiment began with the extraction of base from the unknown three-component mixture provided. This mixture was dissolved in ether and placed into a separatory funnel. 5% hydrochloric acid was subsequently added and mixed in order to separate the solution into layers, releasing the pressure in the stoperred and stopcocked funnel after each inversion, swirl and shake of the solution. The lower layer was drained into a flask and the process was repeated twice, adding 5% hydrochloric acid first and then using water. The lower layer was drained into the same flask each time, labelled as hydrochloric acid extract. This liquid was set aside, containing the hydrochloride salt of the organic amine. In step 3, the acid and neutral compounds were separated from within the mixture. Using the ether layer remaining in the separatory funnel, 5% sodium hydroxide was added and mixed into the solution to separate the layers, venting after each inversion of the stoperred and stopcocked funnel. The lower layer was drained into a separate flask and this process was repeated twice, first with 5% sodium hydroxide solution and then with water, draining into the same flask each time. The flask was labelled as sodium hydroxide extract and set aside, containing the sodium salt of the organic acid. The neutral compound was then isolated by pouring the ether layer through the neck of the funnel, as to not come into contact with other substances, into a flask and adding anhydrous sodium sulfate. The solution was swirled and left to stand
for about 15 minutes, subsequently being filtered by gravity filtration into a previously weighed beaker. The sodium sulfate was rinsed with ether and placed in the fume hood to allow the ether to evaporate, eventually leaving the neutral compound residue which was weighed for percent recovery. Step 4 involved the use of the collected hydrochloric acid extract, cooling the solution in an ice-water bath and stirring in 10% aqueous sodium hydroxide to make the solution basic. The precipitate that formed within the flask was collected using vacuum filtration and transferred to a preweighed watch glass to be air-dried and weighed to report the percent recovery. A similar process was performed in step 5, cooling the sodium hydroxide extract in an ice-water bath and gradually stirring in 10% hydrochloric acid to make the solution acidic. The precipitate formed within the mixture was collected using vacuum filtration and transferred to a pre-weighed watch glass to be air-dried and weighed for the percent recovery. One of the compounds produced in the lab, acid, base, and or neutral, were chosen to be identified by melting point measurement using reference samples in step 6. The three substances, one experimental and two reference, were placed in a melting point apparatus to confirm their identity by performing mixed melting point determinations.
Results: Masses of Products Starting mass of the mixture: 1.500 g Mass of Watch Glass/Beaker (g) Mass of Watch Glass/Beaker + Isolated Compound (g) Mass of Isolated Compound (g) Percent Recovery Basic Compound 31.394 31.852 0.458 30.53% Acidic Compound 33.201 33.230 0.029 1.933% Neutral Compound 50.198 50.280 0.082 5.467% Percent recovery calculations Basic compound: Pure I m m p a u ss r e o m f i a s s o s l a o t f e d m c ix o t m ur p e o ( u g n ) d ( g ) × 100% = × 100% = 30.53% Acic compound: Pure I m m p a u ss r e o m f i a s s o s l a o t f e d m c ix o t m ur p e o ( u g n ) d ( g ) × 100% = × 100% = 1.933% Neutral compound: Pure I m m p a u ss r e o m f i a s s o s l a o t f e d m c ix o t m ur p e o ( u g n ) d ( g ) × 100% = × 100% = 5.467% Melting Point Comparison Our basic product (°C) Ethyl p-Aminobenzoate (°C) P-Chloroaniline ( °C)
Experimental melting point: 78.6-81.5 90.4-93.4 68.5-72.9 Literature melting point: N/A 88-90 70-72 Based on the melting point of our basic compound, compared with the melting points of the known basic compounds, it is most likely that our unknown compound is p- Chloroaniline. Although the melting point for our unknown compound is slightly higher than that of p-chloroaniline, it is still closer than the melting point of ethyl p- aminobenzoate, indicating that p-chloroaniline is the best option of the two. Discussion: Part A Liquid-liquid extraction, otherwise known as solvent extraction, is a method used to separate the components within a liquid mixture by pulling the compounds, or solutes, within a solution from one solvent to another.² This involves the countercurrent movement of solutes from within solutions using other immiscible solvents that the solutes are soluble in.¹ Extraction methods differ depending upon the density of the solvents being used, since solvents that are more or less dense than water will require different or additional glassware.² The most common method is performed using repetitive extraction with a separatory funnel. Effective separation strategies by extraction can be planned by using the pKa values of the compounds that are used. Using these acid and base properties of
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