TLC Post Lab
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Jan 9, 2024
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Uploaded by MajorEnergy12892
Name: Suzanne Varughese
Section: L16
TA: Baily Morton
TLC Post Lab
1.
Data Collection - make a table of Rf values for each of the solvent systems that were tested (solvent system/ Rf value for ferrocene / Rf value for acetylferrocene). You do not need to show your work for the Rf values. It would be beneficial to add any pictures you may have to provide context for abnormal results (example - 100% ethyl acetate would NOT give any Rf values below 0.5).
EA (ethyl acetate)
Group # 1 (0mL heptane, 10mL EA)
Rf value for ferrocene (mL)
Rf value for acetylferrocene (mL)
0
0.969
0
0.909
0
0.951
Group # 2 (2mL heptane, 8mL EA)
Rf value for ferrocene (mL)
Rf value for acetylferrocene (mL)
0.824
0.971
0.847
0.969
0.791
0.940
Group # 3 (5mL heptane, 5mL EA)
Rf value for ferrocene
Rf value for acetylferrocene
0.517
0.172
0.903
0.661
0.936
0.696
0.950
0.772
Group # 4 (8mL heptane, 2mL EA)
Rf value for ferrocene (mL)
Rf value for acetylferrocene (mL)
0.901
0.346
0.857
0.476
0.955
0.591
0.871
0.355
Group # 5 (10mL heptane, 0mL EA)
Rf value for ferrocene (mL)
Rf value for acetylferrocene (mL)
0.621
0
0.565
0
0.571
0
0.516
0
2.
Analysis - which of the solvent systems would be the best choice to separate these two compounds on a column? From the data above, I would choose solvent system from group #4 to be the best choice to separate the two compounds on a column. Looking at the data, it shows that group 4 has a greater separation distance between the Rf values. In group 4 we have 8mL heptane and 2 mL ethyl acetate. Heptane is less polar than ethyl acetate. This polarity allows heptane to travel further and faster on the plate compared to a polar substance. Since we have more heptane in this system, the ferrocene can travel further and faster than acetyl ferrocene. This results in a greater distance between both allowing
the separation of the compounds to be better.
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If all of the components have a reasonably similar size and molecular weight, which of the suspected components is the most polar?
X
Y
Z
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when the eluent is 40% ethyl acetate, 60 % hexane. Indicate, what is the most polar and least
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--
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Thanks!
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Pease indicate the compound that best fits in the blank of the separation scheme below.
OH
H2N
Benzoic Acid
Biphenyl
Benzocaine
Phenol
benzocaine
phenol
biphenyl
benzoic acid
dissolve in ether; extract with aqueous 19)_
ether
aq
20)
CO:(g)
H2O
HIDDEN COMPOUND 1
HIDDEN COMPOUND 2
HIDDEN COMPOUND 3
trace 21)
|6.0M
М НСI
aq
NaCl
22).
HO
Which of the following is the best choice for blank 21 in the given separation scheme?
O H2SO4
O pentane
O HCI
NaHCO3
O H20
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Pease indicate the compound that best fits in the blank of the separation scheme below.
OH
H2N
Benzoic Acid
Biphenyl
Benzocaine
Phenol
benzocaine
phenol
biphenyl
benzoic acid
dissolve in ether; extract with aqueous 19)_
ether
aq
20)
CO,(g)
H2O
HIDDEN COMPOUND 1
HIDDEN COMPC
HIDDEN COMPOUND 3
trace 21)
|6.0 М НСI
aq
22)
NaCl
H20
Which of the following is the best choice for blank 22 in the given separation scheme?
phenol
O benzocaine
O biphenyl
water
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Please answer both 1 and 2 (picture below is the same question attached )
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7-9
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CI
NH
'N'
chloroquine
CI
NH
LHO
N.
N:
hydroxychloroquine
5. You attempted to separate chloroquine and hydroxychloroquine using paper
chromatography. You used a mixture of benzene and pyridine as your solvent.
What results can you expect?
O Two bands: hydroxychloroquine will have a higher Rf than chloroquine
One band: Both will have equal Rf
Four bands: The enantiomers of each analyte will appear as separate bands
Two bands: chloroquine will have a higher Rf than hydroxychloroquine
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GC-MS data (gas chromatography): Illustrated in picture
*ignore peak at 8.87 minutes
Peak 1 mass = 96.2 (1-methylcyclohexene)
Peak 2 mass = 96.2 (3-methylcyclohexene)
Peak 3 mass = 114.2 (impurity)
IR Spectra (Infrared Spectroscopy): Illustrated in picture.
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pyright Cata Education 220
2. When should you stop the distillation process for this procedure?
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water will be added to the reaction when 1.25 mL of 85 % H;SO, is added?
4. What peaks in the IR spectrum would indicate the loss of 1-hexene and the formation of
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OH
HO
Hydroxymethyl-
cyclohexanol
MW: 114
bp: 183
2-Hydroxyethyl-
cyclohexanol
MW: 144
Methylcyclohexane
Methylacetate
MW: 98
bp: 101
mp: -127
d: 0.77
MW: 74
mp: -43
d: 0.93
bp: 270
mp: not available
d: 0.98
bp: 57
mp: not available
d: 0.98
Compound 4
Compound 2
Compound 3
Compound 1
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compounds?
a) Perform a fractional distillation on the mixture.
b) Benchtop silica gel column chromatography.
c) Dissolve the mixture in an organic solvent and treat the solution with aqueous HCI.
d) Dissolve the mixture in an organic solvent and treat the solution with aqueous NaOH.
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1. Answer true or false for each statement:
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b) Carboxylic acids containing six or more carbon atoms per molecule are more soluble in2.5 M sodium hydroxide than in diethyl ether.
c) Phenols containing six or more carbon atoms per molecule are more soluble in 2.5 M sodium hydroxidethan in diethyl ether.
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---4--4--
R 0.50
R0.30
No, the Rf values are too close together
No, there should be more lanes on the TLC plate
Yes, the image illustrates two different compounds
O Yes, multiple of each type of compound are shown on the plate
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Answer last 3
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A mixture of tert-butylbenzene and acetophenone is adsorbed onto a silica gel chromatography column and eluted with a
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least polar
tert-Butylbenzene
elutes first
most polar
elutes last
Answer Bank
Acetophenone
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Which one is the more polar component? Explain.
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aqueous.
4-methylacetophenone
soluble aluminum salt (A1C13 destroyed by aqueous HC1)
acetic acid (from any unreacted acetyl chloride)
trace toluene
hydrochloric acid
water
methylene chloride
aq
soluble aluminum salt
acetic acid
hydrocholic acid
water
multiple Extractions with water and methylene chloride
organic
4-methylacetophenone
methylene chloride
trace toluene
trace acetic acid, and H₂O
trace 3)
organic
4-methylacetophenone
methylene chloride
trace toluene
trace water
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aq
5)
sodium chloride
water
CO₂(8)
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Cuvette 2 - 75%: 0.466 absorption
Cuvette 3 - 50% dye: 0.311 absorption
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additional information on strengths oj
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