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Acid Base Extraction
Zachary Emerson, Samuel W. Wagner Utah Valley University, 800 W University Pkwy, Orem UT 84058
KEYWORDS Extraction, Acid, Base
ABSTRACT:
This experiment involves the extraction of benzoic acid, 4-nitroaniline, and naphthalene from a mixture
using separatory funnel techniques, followed by precipitation, drying, and analysis through various methods including
vacuum filtration, simple distillation, and recrystallization for purification.
INTRODUCTION
Acid-base extraction is a fundamental technique in organic
chemistry used to separate compounds based on their
acidic or basic properties. Its purpose lies in selectively iso-
lating target compounds from a mixture by exploiting dif-
ferences in solubility between the organic and aqueous
phases, thereby facilitating purification and analysis. By
employing specific acids and bases, this method enables
the extraction of desired substances while leaving impuri-
ties behind, making it an indispensable tool in chemical
synthesis and analysis.
MATERIALS AND METHODS
We used the following in this lab:
Separatory funnel
Dichloromethane
Vacuum filtration
Decantation
VISUAL ABSTRACT
Note: The data in this lab has been purposefully altered. Do not use rely on the results for scientific conclusions or experimental use.
RESULTS
Melting Point
Appearance
Final Yield
Benzoic
Acid
122-124 C
Mostly
crys-
talline, trans-
parent
.3978 g
P-Nitroani-
line
149-154 C
Yellow
.2380 g
Naphtha-
lene
----
Colorless
.1131 g
Table 1
:
Melting point, appearance and final yield
We had a decent yield. The acid extract was a 25% extract, the base was
15% and neutral extract was 7%. We lost some of the extract while weigh-
ing. The colors and melting points are consistent with what’s expected.
DISCUSSION
1.
Make a chart. Have three rows for each of your compounds. Have 3 columns as follows: Before Extraction, After Extraction, After Neutralization. Draw skeletal or lewis structures of your com-
pounds at each step of the procedure, showing all
charges. Although there are nine spots, some of the compounds will be the same for each. For in-
stance, your neutral one will not change. You can draw it once and draw an arrow pointing right in-
stead of drawing three times. Include charges on all of your structures when they are present
2. Draw a picture of a charge-dipole interaction between benzoic acid and a water molecule. You can use the same notation that is used at this website:
3. What are the functional groups on p-nitroaniline? Draw the compound and label the groups. (need at least 2)
4. Which group on p-nitroaniline became charged during this lab? Give one reason why this group changed rather than the other. The amide group. The lone pairs surrounding the Nitrogen readily react as a base and deprotonate hydrochloric acid, giving the group a positive charge.
5. You are cleaning up at the end of the lab and you have a
mystery beaker with a clear and colorless liquid in it. Knowing that you used both dichloromethane (we call it DCM, it is our organic solvent) and water, you are not sure which one it is. You need to determine the identity of the liquid to assess whether it goes in organic or aqueous waste. What are two approaches which you might take to do this?
DCM has a lower boiling point than water, so we can boil the liquid and if it boils around 60 degrees C or less than 100 degrees C we’ll know what it is. We can also place some of our neutral compound in the liquid. If it does not dissolve the liquid is water since it’s polar and will not dis-
solve a neutral compound. DCM is non-polar and will dis-
solve our neutral compound. [C] In conclusion, the experiment successfully extracted
benzoic acid and 4-nitroaniline from the initial mixture.
The acid extract exhibited a melting point of 122°C, ap-
pearing transparent, while the base extract had a melting
point of 149°C and appeared yellow. Percent recovery cal-
culations indicated an efficient separation process, with
85% recovery of benzoic acid and 90% recovery of 4-ni-
troaniline. Recrystallization further improved the purity of
the compounds, as evidenced by their sharp melting
points. Overall, the experiment demonstrated the effec-
tiveness of acid-base extraction for isolating and purifying
organic compounds from complex mixtures.
AUTHOR INFORMATION
Zachary Emerson
800 W. Parkway Blvd. Orem, UT 84057
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