Experiment 5: Extraction

Joseph Personelli
Lab Partner: Benjamin Lowry
Organic Chemistry 1
Dr. Joseph Kappel
LA: Stacey Mendigutia
3/10/15

Abstract:

The purpose of this experiment was to evaluate the effectiveness of an

extraction technique involving acidic, basic, and neutral compounds. The products
that were sought were 9-fluorenone, the neutral component, benzoic acid, the
acidic component, and ethyl 4-aminobenzoate, the basic component. The
hypothesis was accepted but with reservations. The melting points determined
backed the hypothesis but the percent recoveries of 18.8% for benzoic acid and
71.53% for ethyl 4-aminobenzoate indicated that there was an error during the
experiment.

Introduction

The purpose of this experiment was to utilize, observe, and determine the
effectiveness of an extraction technique for use on acidic, basic, and neutral compounds.
Extraction is a laboratory technique that is utilized to isolate a product or to purify a
product from a compound.
The extraction method that was utilized throughout this experiment was liquidliquid extraction. According to UCDavis liquid-liquid extraction is a method by which a
compound is pulled from solvent A to solvent B where solvents A and B are not
miscible.2 This was accomplished when the acids and bases, hydrochloric acid and
sodium hydroxide, were brought together into a prepared mixture of already acids and
bases. These aforementioned acids and bases were added to have the already present
acids and bases react for easy separation.
After extraction the melting point and the percent recovery were then calculated
to ensure that the experiment was properly performed. The melting point refers to the
temperature in which the recrystallized product changes from a solid to a liquid. This
helps to determine the purity of the product. The percent recovery determines how much
of the recrystallized product forms divided by the initial amount added.
The acid that was extracted was benzoic acid. The basic component of this
experiment was the ethyl 4-aminobenzoate. Finally, the neutral component of this
experiment was the 9-fluorenone.
It was hypothesized that a liquid-liquid extraction technique could be utilized to
extract acids, bases, and neutral compounds from a mixture.

Benzoic Acid

Ethyl 4-aminobenzoate

9-Fluorenone

Materials and Methods:

For information on the method of extraction, please refer to Chapter 6,

Experiment 4C on pages 147-150 from the Lab manual of Microscale Organic
Laboratory with Multistep and Multiscale Syntheses by Dana W. Mayo, Ronald M. Pike,
and David C. Forbes. No alterations were made do this procedure.

Results:

Table 1: Initial measurements of added compounds

Mass of 9-Fluorenone (g)
0.053
Mass of Ethyl 4-Aminobenzoate (g)
0.052
Mass of Benzoic Acid (g)
0.054
Mass of Anhydrous Salt (g)
0.3063
Table 1 shows the mass measurements of the added acid, base, neutral compound and
salt.

Table 2: Extracted Compounds

Mass of beaker and boiling stones (g)
Mass of filter paper (1) (g)
Mass of filter paper (1) and Ethyl 4-

8.476
0.1039
0.1411

Aminobenzoate (g)
Mass of filter paper (2) (g)
Mass of filter paper (2) and benzoic acid

0.1040
0.1142

(g)
Table 2 shows the measurements of extracted componenets

Table 3: Calculations and Recovery Mass (g)

Percent Recovery (%)
Ethyl 4-Aminobenzoate
0.0372
71.53
Benzoic Acid
0.0102
18.8
Table 3 shows the calculated masses of the acidic and basic components as well as the
percent recovery of each.

Table 4: Melting points of extracted compounds

Benzoic Acid (oC)
110

Ethyl 4-Aminobenzoate (oC)

87
o
9-Fluorenone ( C)
64
Table 4 shows the melting points of the extracted compounds

Calculations:

Mass of Ethyl 4-Aminobenzoate: mass of filter one and compound initial mass of
filter paper = 0.1411 0.1039 = 0.0372

Mass of Benzoic Acid: mass of filter paper two and compound initial mass of filter
paper = 0.1142 0.1040 = 0.0102

Percent Recovery of Ethyl 4-Aminobenzoate: (final mass / initial mass) * 100 =

(0.372 / 0.052)* 100 = 71.53 %

Discussion:

The purpose of this experiment was to utilize, observe, and determine the
effectiveness of an extraction technique for use on acidic, basic, and neutral compounds.
One of the techniques utilized during this experiment was a liquid-liquid extraction. To
determine the effectiveness the percent recoveries were calculated.
The percent recovery of the benzoic acid and the ethyl 4-aminobenzoate, as seen
in Table 3, were 18.8% and 71.53% respectfully. The percent recovery of the 9-

fluorenone was not calculated due to some errors that occurred during the lab. The initial
masses regarding the 9-fluorenone were not taken and therefore could not be utilized in
calculating the percent recovery.
The melting points of the recovered products, as seen in Table 4, were determined
and compared to the standards of the lab manual to ensure that the products extracted
were pure. According to the lab manual the melting points of benzoic acid, benzoate
product, and 9-fluorenone are 122C, 89C, and 84C respectfully. The melting points of
the extracted products of benzoic acid, benzoate product, and 9-fluorenone were
determined to be 110C, 87C, and 64C respectfully. After comparing the extracted
products to the standards of the lab manual it can be determined that the extraction of the
benzoate product was the most pure. The melting point of the extracted 9-fluroenone was
about 20C cooler than the standard from the manual.
An error that occurred that could have had an influence on the results that were
calculated and recorded was that the lid was left off of the anhydrous salt bottle. The
moisture of the South Florida air could have been absorbed resulting in data that is
incorrect. To eradicate this from future experiments the lid should be replaced
immediately after the appropriate amount of anhydrous salt was taken.

Conclusion:

The hypothesis of this experiment was accepted but with reservations. It was
accepted because the percent recoveries and the melting points were able to be
determined by means of perform the extraction technique. However, the reservations

arise in the calculated percent recoveries: benzoic acid and the ethyl 4-aminobenzoate
with 18.8% and 71.53% respectfully. One suggestion to improve this experiment is to
keep the anhydrous salt closed and put away when not needed.
Questions:
6-23: The solubility of p-dibromobenzene would be greater if dissolved by acetone than
by benzene. The atoms of the element bromine have a high electronegativity resulting in
a polarity that is localized. Because p-dibromobenzene has specific polarity it will
dissolve in acetone.
6-24: The standard density of methylene chloride is 1.326 g/cm. This means the
methylene chloride will form a low layer and the ice cube will float on top of it due to the
ice cubes density ~1. Pentane has a lower density compared to the ice cube 0.626 g/cm
meaning the pentane layer will form above the ice cube. The same is true for toluene
the layer will form above the ice cube because the ice cube is more dense compared to
the density of toluene, 0.867 g/cm. Like the two aforementioned solvents, diethyl ether
will also form a layer above the ice cube because the density of the diethyl ether is 0.713
g/cm.
References
1

Mayo, D. W., Pike, R. M., & Forbes, D. C. (2011). Microscale Organic Laboratory
with Multistep and Multiscale Synthesis. Hoboken: John Wiley & Sons, Inc.

Liquid-Liquid Extraction. (n.d.). Retrieved April 12, 2015.

<http://chemwiki.ucdavis.edu/Reference/Lab_Techniques/LiquidLiquid_Extraction>