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NEW Organic Chem Lab - 4C Experiment Lab Report

This lab experiment aimed to practice solvent extraction techniques by separating a mixture of an acid and neutral compound using acid-base extraction. The procedure involved mixing 9-fluorenone and either benzoic acid or ethyl 4-aminobenzoate, then adding diethyl ether, HCl, and NaOH to extract the components based on their changing polarities. Percent yields were calculated for the recovered 9-fluorenone and acid/base. Adding the acid and base turned the mixture into organic salts, increasing the solubility of each product in the aqueous layer and allowing separation by extraction.

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67 views

NEW Organic Chem Lab - 4C Experiment Lab Report

This lab experiment aimed to practice solvent extraction techniques by separating a mixture of an acid and neutral compound using acid-base extraction. The procedure involved mixing 9-fluorenone and either benzoic acid or ethyl 4-aminobenzoate, then adding diethyl ether, HCl, and NaOH to extract the components based on their changing polarities. Percent yields were calculated for the recovered 9-fluorenone and acid/base. Adding the acid and base turned the mixture into organic salts, increasing the solubility of each product in the aqueous layer and allowing separation by extraction.

Uploaded by

chelsea natalie
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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Organic Chem Lab


Solvent Extraction II: Acid-Base Extraction Using A Two-Component Mixture of
an Acid and a Neutral Substance (or a Base and a Neutral Substance)

Objective:
The purpose of this lab was to practice using techniques to extract a solvent. Materials such as separatory
and Hirsch funnels were used, which helped enhance skills and knowledge revolving around separating a
mixture of an acid and a neutral compound.

Experimental Procedure:
The procedure was followed as described in Mayo, pages 147-150, with the modifications listed in the
posted Canvas document. Additional modifications to the procedure included the following:
● Used 75 mg of the compounds instead of 50 mg
● Used either 9-fluorenone and benzoic acid OR 9-fluorenone and ethyl 4-aminobenzoate
● Used unchanged solvent amounts
● Used a 15-mL centrifuge tube to mix the components
● Used flowchart to look at steps required based on which components were used
● Only found the melting point of the recovered 9-fluorenone.

Reaction Scheme

Data and Results

Benzoic Acid 9-Fluorenone Diethyl Ether HCI NaOH

Mol. Formula C7H6O2 C13H8O C4H10O HCI NaOH

Amount (mg) 75 mg 75 mg

Amount (mL) 4.0 mL 2.0 mL 2.0 mL

mmoles 0.41 0.27

Concentration (M) 6.0 M 3.0 M

Molar Mass 122.12 g/mol 180.20 g/mol 74.12 g/mol


Density (g/mL) 1.266 g/mL 84.3 mL 1.110

mp (℃) 122.0 84 12

bp (℃) 250.0 342 135

Observations:
● 9-Fluorenone was a solid yellow color
● No separation occurred before adding the base
● Top organic layer was tinted yellow
● Litmus paper turns red to show acidity

Calculations:
● Yield of 9-fluorenone recovered from diethyl ether layer
- (0.41 mg/0.78 mg) x 100 =52.6%
● % Yield of 9-fluorenone
- 12.788 g(after drying)- 12.776 g (tared vial) = 0.035 g
● Yield of benzoic acid or ethyl 4-aminobenzoate recovered from aqueous layer (3 M
NaOH or 3 M HCl) = 21.0 mg
● % Yield of benzoic acid or ethyl 4-aminobenzoate
- (21.0 mg / 75.0 mg) x 100 =28.0 %

Questions:
1.

2. a.) Both compounds are soluble in diethyl ether before adding NaOH and HCl since they are both
nonpolar. Both of these reactions increase the solubility of each of the products in the aqueous layer.

b.) Adding HCl and NaOH to the mixture both turn it into organic salts, which then increase their
solubility in water. The acid and base products end up increasing in polarity, therefore, the new mixture
can now be soluble in water.
Works Cited
1. Mayo, D. W.; Pike, R. M.; Forbes, D. C. Microscale Organic Laboratory with Multistep and Multiscale
Syntheses, 5th ed.; John Wiley & Sons, Inc., 2011; pp 147-150.

2. Modifications for Expt 4C: Solvent Extraction II, Canvas document.

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