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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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Acid-Base Extraction
4
8.
To the remaining organic layer, add 20 ml of saturated sodium chloride solution, extract, and collect the bottom layer.
9.
Drain the organic layer into a conical flask labeled #3, add anhydrous sodium sulfate to dry, filter, and retain the filtrate.
10.
Evaporate the ether from the filtrate to obtain dry crude naphthalene.
11.
Record masses of recovered compounds and measure their melting points for purity assessment. Compare values with literature.
Results
Compound
3M HCL
3M NaOH
Diethyl Ether
water
Benzoic Acid
I
S
S
P
4-Chloroaniline
S
p
S
P
Naphthalene
p
p
s
P
Table 1
Table 2
Compound
Initial Weight (g)
Final Weight (g)
Benzoic Acid
1.022
1.0664
4-Chloroaniline
1.009
1.650
Naphthalene
1.004
0.2011
Table 3
Acid-Base Extraction
5
Compound
Began melting (°C)
Finished melting (°C)
Literature point(°C)
Benzoic Acid
68
75
72.5
4-Chloroaniline
111
120
122.3
Naphthalene
82
88
80.26
Benzoic acid
Theoretical yield
−
1.022
122.12
∗
100
=
0.820
Percent yield
−
1.066
0.820
∗
100
=
130%
4-Chloroaniline
Theoretical yield
=
1.009
127.57
∗
100
=
0.790
Percent yield
−
1.560
0.790
∗
100
=
197.46 %
Naphthalene
Theoretical yield
=
1.004
128.18
∗
100
=
0.783
Percent yield
−
0.2011
0.783
∗
100
=
26.94%
Discussion
In order to comprehend the behavior of organic compounds (benzoic acid, 4-chloroaniline, and naphthalene) based on polarity, acidity/basicity, and compound-solvent interactions, the solubility of these compounds in different solvents was investigated in this experiment. The solubility properties of the compounds are illustrated by the data listed in Table 1. The insolubility of benzoic acid in 3M HCl
Acid-Base Extraction
6
demonstrated its resilience to strong acids. Its acidic character was emphasized by its solubility in 3M NaOH, where it reacted with the base. Its partial solubility in water demonstrated its polar characteristics, whilst its solubility in diethyl ether indicated non-polarity.
Comparably, 4-chloroaniline demonstrated basic behavior, reflecting its polar properties, with solubility in 3M HCl, limited solubility in 3M NaOH, and total solubility in diethyl ether and water. The behavior of naphthalene showed signs of non-polarity, such as partial solubility in 3M HCl and 3M NaOH, total solubility in diethyl ether, and partial solubility in water. The theoretical yields were computed under the assumption of a 1:1 molar ratio before moving on to percent yield and purity evaluations. High percent yields (130% and 197.46%, respectively) for benzoic acid and 4-chloroaniline indicated effective separation. Their melting points were in good agreement with values reported in the literature, indicating excellent purity. On the other hand, naphthalene showed a lower yield percentage (26.94%), suggesting possible inefficiencies or losses. There's a chance that contaminants impacted the purity because the observed melting points were somewhat higher than those found in the literature.
Conclusion
Three chemical molecules were separated and characterized in this acid-base extraction experiment: naphthalene, 4-chloroaniline, and benzoic acid. Understanding molar ratios, experimental procedures, and solubility principles were critical to the separation process's success. Based on the compounds' acidity, basicity, and polarity, the solubility tests carried out in a range of solvents offered insightful information about how the compounds behaved. While benzoic acid reacted with bases to reveal its acidic nature, it also showed resistance to strong acids. 4-Chloroaniline behaved in basic manner, but naphthalene showed different solubility patterns due to its non-polar nature. The theoretical yields that
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were computed, under the assumption of a 1:1 molar ratio, made it possible to evaluate the separation efficiency. Successful isolation was demonstrated by the high percent yields of 130% and 197.46% for benzoic acid and 4-chloroaniline, respectively. These compounds' reported melting points showed good agreement with values found in the literature, demonstrating their great purity. Conversely, naphthalene posed difficulties due to its lower production percentage of 26.94%. The somewhat higher melting points indicated the possibility of contaminants reducing the product's purity. To increase efficiency, the naphthalene separation method may need to be further optimized. Together, the solubility testing, melting point studies, and theoretical yield computations provide a thorough grasp of the separation procedure. The experiment effectively demonstrated the application of organic chemistry concepts, highlighting the significance of chemical properties, molar ratios, and solvent choice. Further investigations might yield better results by optimizing the naphthalene separation process and investigating substitute solvents or methods. Furthermore, a more thorough examination of the impurities influencing the melting points can improve the compound purity evaluation.
In conclusion, this acid-base extraction experiment not only demonstrated the practical application of solubility concepts in organic chemistry but also highlighted the importance of careful experimental design for efficient and pure compound isolation. The insights gained contribute to the broader understanding of separation techniques and their relevance in organic synthesis
Acid-Base Extraction
8
References
Pandey, Weldeggirma, & Hoare. (n.d.). Organic Chemistry I laboratory Manual
P. (n.d.). PubChem
. PubChem. https://pubchem.ncbi.nlm.nih.gov/
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