Module 1 - Solvent Extraction and Partition Coefficient Part A
pdf
keyboard_arrow_up
School
Temple University *
*We aren’t endorsed by this school
Course
2203
Subject
Chemistry
Date
Feb 20, 2024
Type
Pages
5
Uploaded by ProfTurkey3920
CHEM 2203
Experiment 4A: Calculation and Comparison of the Solubility of 9-Fluorenone in a Mixture of
Methylene Chloride and Water through the Implementation of Solvent Extraction, Establishing
Equilibrium Distribution, and Isolation to Determine the Partition Coefficient at the Microscale
Level
Objective: The goal of this experiment is to separate the created solution into an aqueous mixture
and an organic mixture and record all findings, to eventually calculate the partition coefficient.
The Techniques that are new will include separation of a solid precipitation from a liquid by
using a glass filtered pipet and heater block, weighing and measuring substances in mL and mg,
and usage of automatic delivery pipettes.
Experimental Procedure: The procedure was followed as described in Mayo, pages 144-145,
with the modifications listed in the Canvas document. Additional modifications to the procedure
included the following: Use of 2mL Methylene Chloride.
Additional Modification: approx. 0.094g 9-fluorenone was substituted for the intended .075g.
Reaction Scheme: There was no reaction included in this experiment.
Data and Results:
9-Fluorenone
Methylene Chloride
Water
Mol. Formula
C
13
H
8
O
CH
2
Cl
2
H
2
O
Amount (mg)
94
-
-
Amount (mL)
-
1
1
mmoles
.522
-
-
Molar Mass (g/mol)
180.2
84.93
18.02
Density (g/mL)
-
1.33
1
Mp/Bp (ºC)
80-83
40
100
Observations:
1.
The 9-fluorenone was initially a bright yellow grainy substance. The water and
methylene used were both clear in color with the methylene being slightly more opaque.
2.
After the combination of the water, 9-fluorenone, and the methylene in a 5mL conical
vial the solid completely dissolved into the solvents and couldn’t be seen.
3.
The 9-fluorenone turned the bottom organic layer of methylene a slightly yellowish color
and did not alter the color of the water at all.
4.
The tared test tube with a boiling stone inside of it weighed in at approximately 11.697g
5.
The heat of the test tube turned the liquid methylene chloride + 9-fluorenone solution into
a yellowish liquid substance due to the evaporation of a majority of the methylene.
6.
After rolling off the test tube upon a lab table the liquid completely disappeared and left a
yellowish, grainy substance that appeared similar to the initial specimen of 9-fluorenone.
7.
The initial weight of the test tube after the first round of heating and cooling was 11.759g
8.
The constant weight of the test tube after the second round of heating and cooling was
11.759g
Calculations:
1.
Constant weight of test tube with boiling stone and 9-fluorenone - initial weight of the
test tube and boiling stone: 11.759g - 11.697g = 0.062g
2.
Initial weight of 9-fluorenone - (Constant weight of test tube with boiling stone and
9-fluorenone - initial weight of the test tube and boiling stone): 0.094g - 0.062g = .032g
3.
(Constant weight of test tube with boiling stone and 9-fluorenone - initial weight of the
test tube and boiling stone) / (Initial weight of 9-fluorenone - (Constant weight of test
tube with boiling stone and 9-fluorenone - initial weight of the test tube and boiling
stone): 0.062g/mL / 0.032g/mL = 1.9375
Questions:
1.
a.
Carbon to carbon bonds are nonpolar because their electronegativity difference is 0.
Carbon to hydrogen bonds are nonpolar because the electronegativity difference between
them is close to .4, which falls into the nonpolar bond range.
b.
These non-polar regions interact with solvent molecules with london-dispersion forces or
dipole-induced dipole forces. London dispersion forces may be at work because the
nonpolar molecules, carbon and hydrogen, are attracted to each other and temporarily
induced dipole forces. This is because while 9-fluorenone is very nonpolar, the water is
very polar, causing a temporary attraction between them.
c.
Carbon to oxygen bonds are polar because they have an electronegativity difference of
approximately .9, which falls into the polar range. The oxygen will pull more of the
electrons towards it, creating a negative charge for itself and a positive charge for the
attached carbon.
d.
This polar region interacts with solvent molecules through hydrogen bonding. The
oxygen that is double bonded to the carbon would exhibit hydrogen bonding because it is
a one of the three highly electronegative elements (O, N, F), has active lone pairs of
electrons, and is interacting with a polar solvent containing hydrogen.
e.
Based on the answers to parts (a)-(d), I believe that 9-fluorenone would be more soluble
in methylene chloride (a more non-polar organic solvent) than water (a very polar
solvent). This is because the non-polar organic solvent is able to be more attracted to the
large amount of non-polar bonds in the 9-fluorenone while the water only has the one
oxygen atom to work with.
Your preview ends here
Eager to read complete document? Join bartleby learn and gain access to the full version
- Access to all documents
- Unlimited textbook solutions
- 24/7 expert homework help
f.
My experimental partition coefficient was consistent with my prediction in part (e). This
is because both prove that the 9-fluorenone will dissolve better in the non-polar organic
solvent.
2.
a.
If substituted for methylene chloride in this partition coefficient experiment, chloroform
would form the bottom layer due to its density.
b.
Chloroform would form as the bottom layer because it has a higher density than water.
Chloroforms density is 1.49g/mL while water’s density is only 1.0g/mL.
c.
Despite the similarities, methylene chloride is more commonly used than chloroform as
an extraction solvent because it is less dangerous and potentially harmful to humans than
chloroform. While both are somewhat dangerous, methylene chloride poses less of a risk
to experimenter health.
3.
a.
If this experiment is performed with anthracene in place of 9-fluorenone, the partition
coefficient would definitely be higher than the partition coefficient that was obtained for
the 9-fluorenone.
b.
This is explained by the lewis structures of both solutes. While 9-fluorenone has one
polar bond, anthracene has no polar bonds and is made up entirely of non-polar
molecules. This would mean that while 9-fluorenone minimally hydrogen bonds with the
water molecules, anthracene would avoid this entirely. Therefore, the only forces at work
would be the dipole-induced dipole forces between the anthracene and the methylene
chloride, eventually resulting in a 100% yield of the solute in the non-polar organic layer.
4. After the mixture is thoroughly mixed there should be approximately 46mg of the organic
compound in the methylene chloride layer and 10mg of the organic compound in the water layer.
This is because:
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 141-145.
2. Modifications for Expts 4A: Partition Coefficient Part A, Canvas document.
Related Documents
Related Questions
Ethyl heptanoate (EH), a food aroma compound, was added to
water and allowed to come to equilibrium with a known
volume of air and results showed that its partition coefficient,
[EHair]/[EHwater] is equal to 1.8 x 10-2. In the same experiment
with oil in place of water, its partition coefficient, [EHair]/[EHoi]
is found to be lower at 6.0 x 10-6. Account for the difference
between the two values.
arrow_forward
how can i calculate part a
arrow_forward
You add 1 mL of sample and collect 1 mL fractions from a column with a volume of 20 mL where the beads take up 60% of the column and the protein of interest has a partition coefficient of 0.4. What fraction do you want to keep?
arrow_forward
Chemistry
A 50ml aliquot of a 0.1 M solution of a neutral drug was extracted with 2 x 5 ml ethyl acetate. The drug concentration in the combined organic layers was found to be 0.36 M.
Calculate the partition coefficient for this drug under these conditions.
arrow_forward
The partition coefficient for caffeine between dichloromethane and water is 4.6. Assume that a 100 mL tea solution (in water) contained 100 mg of caffeine. What is the theoretical yield of caffeine in the methylene chloride if you extract with one 100 mL portion of methylene chloride?
arrow_forward
Partition coefficients (Kow = organic solvent concentration/aqueous concentration, usually
reported as log Kow) are important for determining how efficiently organic compounds can be
extracted from aqueous solutions. For example, consider the two substances below. Which will be
more soluble in water?
Hexamethylbenzene (log Kow = 6.41)
O Diethyl ether (log Kow = 0.83)
arrow_forward
At 25 °C, the octanol-water equilibrium partition coefficient KOW of Compound X is 150,000 and its water-gas phase equilibrium partition coefficient KWA is 5000. Estimate the octanol-gas phase equilibrium partition coefficient KOA of Compound X.
arrow_forward
What is the partition Coefficient of phenazopyridine? With illustration
arrow_forward
If the solubility of a drug is 3.8 g/L and in chloroform 224.9 g/L calculate its partition coefficient.
arrow_forward
Define a molar extinction coefficient and briefly describe how it is measured.
arrow_forward
If the concentration in a bulk solution adjacent to a fibrous
medium is at a concentration cA = 1mM, and partition
coefficient of K = 0.7, what is the concentration in the
%3D
leading edge of the fibrous medium? the answer has units of
mM (canvas does not allow you to enter units or display the
answer with units.)
your answer
mM
arrow_forward
The octanol - water aqueous buffer partition coefficients (P) for a drug used to treat glaucoma were
obtained experimentally at various temperatures (T) and pH values. The results are presented in the
following table:
pH=7.0
0.72
0.84
pH=6.25
pH=7.25
T= 27 C
0.24
0.89
T= 30 C
0.31
1.06
T= 40 C
1.23
1.49
27.4 mg of this drug were dissolved in 100 mL of buffered water (pH=7.0; T=30) and then
partitioned with octanol portions of 37.1 mL. Calculate how many mg of drug will remain in water
after in the first extraction (Fill in ONLY numbers approximated to the 2nd decimal place)
Answer: 19.01
arrow_forward
You left a bowl of refried beans in the refrigerator too long. One day your roommate opens the
fridge and it smells like rotten egg (due to generated hydrogen sulfide, H2S). You immediately run to
the store to purchase activated charcoal to remove the odor. From a quick search online you learn
that the linear partitioning coefficient is 30 m/kg. Assuming that the refrigerator volume is 0.5 m?,
the initial odor concentration is 3.2 ug/m³, and the final concentration is 0.3 ug/m3 , calculate the
minimum mass of adsorbent (in g) you need to purchase.
Enter your final answer with 2 decimal places.
It is proposed to add activated carbon to treat a storm stream with a pollutant concentration of 5.1
mg/L. If the treatment plant has only 22 kg of activated carbon, how many liters of waste stream can
be treated to achieve an equilibrium effluent concentration of 2.0 mg/L? Lab tests show that
Freundlich isotherm coefficients for the activated carbon and the pollutant are K, 0.09 L/kg and n
= 2.8…
arrow_forward
It is found that up to 0.0110 g of SrF2 dissolves in 100 mL of aqueous
solution at a certain temperature. Determine the value of Ksp for
SRF2.
1
2
NEXT >
Based on the given values, fill in the ICE table to determine concentrations of all
reactants and products.
SFF2(s)
Sr**(aq)
2 F (aq)
+
Initial (M)
Change (M)
Equilibrium
(M)
5 RESET
0.0110
8.76 x 10-5
8.76 x 10-4
1.75 x 10-4
1.75 x 103
-0.0110
-8.76 x 10-5
-8.76 x 10-4
-1.75 x 10-4
-1.75 x 103
+x
+2x
-2х
-X
8.76 x 10-5 + x
8.76 x 10-5
1.75 x 10-4 + 2x
1.75 x 10-4 - 2x
arrow_forward
Acetone has a partition coefficient of 13 while DCM has a partition coefficient of 4.6. Why is DCM used for the extraction of caffeine from Black teabags?
arrow_forward
2) Assume you are decaffeinating your coffee by extracting the caffeine out with dichloromethane. Your particular brand of coffee contains 100 mg of caffeine in a 200 mL cup of water. The partition coefficient of caffeine in dichloromethane/water is 8.0 (it is more soluble in the dichloromethane).Answer the following questions about how much caffeine would still be in the 200 mL of water based on two different approaches. You should solve this algebraically. If you use an equation found on the internet, you will need to show how it was derived to receive credit.a) How much caffeine would remain in the water after extracting once with 200 mL of dichloromethane? Show your work.b) How much caffeine would remain in the water after extracting twice, each time with 100 mL of dichloromethane? Show your work.
arrow_forward
Experimentally measured adsorption isotherms often deviate from the
Langmuir model. Explain what causes these deviations, and why the
Langmuir model generally describes chemisorption better than
physisorption.
arrow_forward
1
arrow_forward
2) Consider the following reaction and associated rate law:
X (g) + Y(g) → Z
Rate = k[X] [Y] b
Use the data in Table 1 in the following problems.
Table 1 Reaction Data
[X]。 (M)
[Y]。 (M)
Rate (M/s)
0.882
0.217
283. 07
0.882
0.451
624. 47
0.882
0.572
820.57
0.882
0.882
1308. 22
0.228
0.882
124.96
0.442
0.882
382. 56
0.67
0.882
804. 48
arrow_forward
If the partition coefficient of CBN from water into ethanol is 4, what fraction q of the
CBN would remain in a 424 mL aqueous sample if it was extracted with 69 mL of
ethanol twice?
arrow_forward
A 78 mg sample of an organic compound (molar mass = 84.0 g/mol) is partitioned between 2.00 mL of water and 2.00 mL of methylene chloride. Separation and processing of the organic phase results in the isolation of 58 mg of the organic compound. Calculate the partition coefficient for the compound between methylene chloride and water (Kpmethylene chloride/water). Your answer should reflect the proper number of significant figures.
arrow_forward
R. Atkinson (J. Phys. Chem. Ref. Data 26, 215 (1997)) has reviewed a large set of rate constants relevant to the atmospheric chemistry of volatile organic compounds. The recommended rate constant for the bimolecular reaction of O2 with an alkyl radical R at 298 K is 4.7 × 109 dm3 mol−1 s−1for R = C2H5 and 8.4 × 109 dm3 mol−1 s−1 for R = cyclohexyl. Assuming no energy barrier, compute the steric factor, P, for each reaction. Hint: Obtain collision diameters from collision cross-sections of similar molecules in the Resource section.
arrow_forward
The partition coefficient of iodine between CCl4 and water is Сcc14/CH₂0 = K = 85, where the C₁ represent
the concentration in mol/L of iodine in the solvent.
(a) If you want to extract 90% of the iodine from 100 mL of an aqueous iodine solution in a single extraction,
Calculate the volume of carbon tetrachloride needed.
(b) If you want to extract 90% of the iodine from 100 mL of an aqueous iodine solution in two extractions
of equal volumes, calculate the volume of carbon tetrachloride needed in each.
(c) If ß is the fraction of iodine remaining in the aqueous solution after n extractions with equal volumes of
CC14, show that as n→ ∞, the total required volume of CCl4 per unit volume of water for each extraction
is given by:
Remember that: ln(1+x) ≈ x
2
VCC4,tot
VH₂0
+
몰....
3
In 3
K
arrow_forward
In a FRET experiment designed to monitor conformational changes in T4 lysozyme, the fluorescence intensity fluctuates between 5000 and 10,000 counts per second. Assuming
that 7500 counts represents a FRET efficiency of 0.6, what is the change in FRET pair separation distance during the reaction? For the tetramethylrhodamine-texas red FRET
pair employed ro =
50. Å.
Express your answer to two significant figures and include the appropriate units.
HÀ
?
Ar =
Value
Units
arrow_forward
The partition coefficient K for a compound between dichloromethane and water is determined to be 56 : 1 (K=56). If 10.0 mg of the compound is dissolved in 50.0 mL of water and this solution extracted with 25.0 mL of dichloromethane, how many mg of the compound will remain in the water layer following the extraction procedure? Show you calculations
arrow_forward
SEE MORE QUESTIONS
Recommended textbooks for you

Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning

Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education

Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning

Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education

Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning

Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
Related Questions
- Ethyl heptanoate (EH), a food aroma compound, was added to water and allowed to come to equilibrium with a known volume of air and results showed that its partition coefficient, [EHair]/[EHwater] is equal to 1.8 x 10-2. In the same experiment with oil in place of water, its partition coefficient, [EHair]/[EHoi] is found to be lower at 6.0 x 10-6. Account for the difference between the two values.arrow_forwardhow can i calculate part aarrow_forwardYou add 1 mL of sample and collect 1 mL fractions from a column with a volume of 20 mL where the beads take up 60% of the column and the protein of interest has a partition coefficient of 0.4. What fraction do you want to keep?arrow_forward
- Chemistry A 50ml aliquot of a 0.1 M solution of a neutral drug was extracted with 2 x 5 ml ethyl acetate. The drug concentration in the combined organic layers was found to be 0.36 M. Calculate the partition coefficient for this drug under these conditions.arrow_forwardThe partition coefficient for caffeine between dichloromethane and water is 4.6. Assume that a 100 mL tea solution (in water) contained 100 mg of caffeine. What is the theoretical yield of caffeine in the methylene chloride if you extract with one 100 mL portion of methylene chloride?arrow_forwardPartition coefficients (Kow = organic solvent concentration/aqueous concentration, usually reported as log Kow) are important for determining how efficiently organic compounds can be extracted from aqueous solutions. For example, consider the two substances below. Which will be more soluble in water? Hexamethylbenzene (log Kow = 6.41) O Diethyl ether (log Kow = 0.83)arrow_forward
- At 25 °C, the octanol-water equilibrium partition coefficient KOW of Compound X is 150,000 and its water-gas phase equilibrium partition coefficient KWA is 5000. Estimate the octanol-gas phase equilibrium partition coefficient KOA of Compound X.arrow_forwardWhat is the partition Coefficient of phenazopyridine? With illustrationarrow_forwardIf the solubility of a drug is 3.8 g/L and in chloroform 224.9 g/L calculate its partition coefficient.arrow_forward
- Define a molar extinction coefficient and briefly describe how it is measured.arrow_forwardIf the concentration in a bulk solution adjacent to a fibrous medium is at a concentration cA = 1mM, and partition coefficient of K = 0.7, what is the concentration in the %3D leading edge of the fibrous medium? the answer has units of mM (canvas does not allow you to enter units or display the answer with units.) your answer mMarrow_forwardThe octanol - water aqueous buffer partition coefficients (P) for a drug used to treat glaucoma were obtained experimentally at various temperatures (T) and pH values. The results are presented in the following table: pH=7.0 0.72 0.84 pH=6.25 pH=7.25 T= 27 C 0.24 0.89 T= 30 C 0.31 1.06 T= 40 C 1.23 1.49 27.4 mg of this drug were dissolved in 100 mL of buffered water (pH=7.0; T=30) and then partitioned with octanol portions of 37.1 mL. Calculate how many mg of drug will remain in water after in the first extraction (Fill in ONLY numbers approximated to the 2nd decimal place) Answer: 19.01arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY

Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning

Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education

Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning

Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education

Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning

Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY