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Acid-Base Extraction
Acid-Base Extraction
Thomas Khaleel USF CHM 2210l Organic Chemistry Lab
Acid-Base Extraction
2
Introduction
Acid-base extraction is a powerful technique in organic chemistry, widely employed for the separation and purification of organic compounds from complex mixtures. This laboratory experiment focuses on the principles and applications of liquid-liquid extraction, specifically in the context of separating organic
compounds based on their acidity/basic characteristics. The process involves exploiting the differing solubilities of compounds in various solvents to selectively extract and isolate specific substances.
Materials
Part A: Solubility Tests
1.
Medium-sized test tubes (12)
2.
Rack for test tubes
3.
Benzoic acid
4.
4-Chloroaniline
5.
Naphthalene
6.
3M HCl
7.
3M NaOH
8.
Diethyl ether
9.
Water
Part B: Separation of Benzoic Acid, 4-
Chloroaniline, and Naphthalene
1.
125 ml conical flask
2.
125 ml separatory funnel
3.
Solid mixture containing benzoic acid, 4-chloroaniline, and naphthalene (3 grams)
4.
Diethyl ether
5.
5% HCl
6.
3M NaOH
7.
6M HCl
8.
Ice
9.
Vacuum filtration setup
10.
Saturated sodium chloride solution (brine)
11.
Anhydrous sodium sulfate
12.
Conical flasks labeled #1, #2, and #3
13.
pH paper
Procedure
Acid-Base Extraction
3
Part A: Solubility Tests
1.
Obtain a rack of 12 medium-sized test tubes and label four tubes each for benzoic acid, 4-
chloroaniline, and naphthalene.
2.
Place 10-20 mg of each solid (benzoic acid, 4-chloroaniline, naphthalene) in their respective tubes.
3.
Perform solubility tests by adding 10 drops of 3M HCl, 3M NaOH, water, and diethyl ether to each tube. Note the solubility reactions, adding more solvent if needed.
4.
Record observations in Table 1, marking "s" for soluble, "i" for insoluble, and "pi" for partially insoluble.
Part B: Separation of Benzoic Acid, 4-Chloroaniline, and Naphthalene
1.
Weigh 3 grams of a solid mixture containing equal amounts of benzoic acid, 4-chloroaniline, and naphthalene in a 125 ml conical flask.
2.
Dissolve the mixture in 30 ml of diethyl ether and transfer it to a 125 ml separatory funnel using additional ether for a complete transfer.
3.
Add 30 ml of 5% HCl to the funnel, cap it, and shake vigorously, venting occasionally.
4.
Allow the layers to separate, then drain the lower layer (containing the protonated amine) into a
conical flask labeled #1.
5.
Add 3M NaOH dropwise to generate the amine, leading to precipitation. Cool and filter the solid.
6.
To the remaining organic layer, add 50 ml of 5% NaOH, shake, and draw off the aqueous layer into a conical flask labeled #2.
7.
Acidify flask #2 with 6M HCl, check for acidity with pH paper, collect the precipitate by vacuum filtration, and wash with ice water.
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Related Questions
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Outline a method for how you would separate this solution into its component parts and briefly
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