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CHM 457 Lab 1
CHM 457 Lab 1
1) To separate the mixture of acid, base and a neutral compound into its individual
components.
2) To analyze and identify the compound by melting point determination.
INTRODUCTION
Extraction involve the dissolving method of a compound from a solid into solvent
or from a solution into another solvent. Extraction used to wash the solution of organic
solute in an organic solvent that free from impurities. Acid base extraction is a one of
the type of liquid-liquid extraction. Acid-base extraction involve the different levels of
solubility levels in water and an organic solvent. The uses of acid-base extraction is to
separate the organic compounds from each other based on their own properties. The
differences of acid and base are any substances that have pH value between 0 up to
7 will be considered as acid solution. For base when the pH value occur within 7 to 14
it will be considered as basic. A requirement of a solvent-solvent extraction is the two
solvents must be mostly insoluble into each other.
In this experiment, a mixture that consist of an acid (benzoic acid) will be
separate from a neutral compound. The neutral compound are triphenylmethanol or
1,2,4,5,-tetrachlorobenzene. The mixture of this solution dissolved in diethyl ether.
The mixture of the two solvents must be separates into two layers. It is very important
to note that upper layer is less dense than the bottom layer. NaOH used for extraction
because of the increased evolution of heat during the extraction and potential side
reactions with the solvent. A strong base like NaOH or NaHCO3 used to remove an
acidic compound from a mixture.
MATERIALS
O.24g unknown, 0.12g benzoic acid, 10.0 mL ether, 10.0 mL of 1.0 M NaOH, 6 M
hydrochloric acid, 5 mL saturated NaCl and sodium sulfate.
APPARATUS
125 mL Erlenmayer flak, 125 mL separatory funnel, weighing balance, litmus paper,
test tubes, measuring cylinder, warm water bath, pasteur pipet and melting point
apparatus.
EXPERIMENTAL PROCEDURE
0.24g of unknown and 0.12g of benzoic acid were added to a centrifuge tube.
10.0 mL of ether were added to the tube and capped it. The tube was shaken until all
the solid dissolved completely. The solution were transferred into a 125 mL
separatory funnel. Then, 5.0 mL of 1.0 M NaOH were added to the separatory funnel
and shaken for 30 seconds. The layers were separated. The bottom (aqueous) were
removed and placed in the Erlenmeyer flask and labeled as “1st NaOH extract”.
Another 5.0 mL portion of 1.0 M NaOH added to another funnel and shaken for 30
seconds. When the layers separated, the aqueous layer were removed and put in
Erlenmeyer flask and labeled as “2nd NaOH extract”
6 M HCl added drop wise to each of the two test tubes that contained NaOH
extracts until the mixture were acidic. The mixture were tested with litmus paper to
determine when they are acidic. The amount of the precipitate observed. To the ether
layer in the separatory funnel, 5.0 mL of saturated aqueous sodium chloride were
added. The solution were shaken for 30 secondhand the layers were separated.Then,
the aqueous layer were discard and removed. The ether layer poured from the top of
the separatory funnel into a clean and dry Erlenmeyer flask. The ether layer dried over
granular anhydrous sodium sulfate. The dried ether solution were transferred to a dry
Erlenmeyer flask and preweighed the flask. The ether were evaporated by heating the
flask in a warm water bath. When the solvent been evaporated, the flask was
removed from the bath and dried outside the flask. Once it cooled to room
temperature, the flask was weighed to determine the amount of solid solute that was
in the ether layer. The melting point of solid were obtained and identified according to
the given table.
RESULTS
Actual weight of benzoic acid = 0.214g
Weight of benzoic acid recovered = 0.0535g
Observed melting point of benzoic acid = 121℃
Percent recovery of benzoic acid = 25%
QUESTIONS
1) List 4 water-immiscible liquids other than ether that could be used to extract
organic compounds from aqueous solution.
Chloroform, cyclohexane, dichloromethane and carbon tetrachloride
3) Draw the structure of the product when benzoic acid react sodium hyroxide. Why is
the product of this reaction easily extracted into H2O, while the original benzoic acid is
not so easily extracted into H2O?
OH removed H+ to form a salt. The polar salt is soluble in aqueous solution. OH
and benzoate are bases. The stronger base takes H+ to form the weaker base.
4) Why does benzoic acid precipitate out when the aqueous layer is acidified with
HCl?
This is because benzoic acid is a stronger base compared to Cl . So it will take H+
from HCl and precipitate out of the solution.
Water
ether
REFERENCES
1) https://study.com/academy/lesson/acid-base-extraction-theory-purpose-procedure.html
2) http://www.chem.ucla.edu/~bacher/Specialtopics/extraction.html
3) https://frtr.gov/matrix2/section4/4-15.html
4) https://people.chem.umass.edu/samal/267/owl/owlextract.pdf
5) https://www.thevespiary.org/rhodium/Rhodium/chemistry/extraction_theory.html