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NAME: Evan Pfeifer

DATE: 7/8/2016
Organic Chemistry: Extraction of Fat and Thin-Layer
Chromatography
INTRODUCTION/GOALS OF EXPERIMENT
In this lab, students measure fat in potato chips and determine the
polarity of several solvents with a chromatography. When measuring chip fat,
the students use a solvent to draw out the fat by evaporating the solvent to
obtain fat. Students build on chromatography skills learned in CHEM 1001,
but focuses on the polarity aspect to discover the composition of an
unknown substance.

RESULTS
Part 1: Extraction of Fat from Potato Chips
Sample 1 (Regular)
Mass of dish +
chips
Mass of empty
dish

Sample 2 (Baked)

27.85 g

29.73 g

25.17 g

26.40 g

2.678 g

3.327 g

29.59 g

26.53 g

28.74 g

26.40 g

Mass of fat

0.8470 g

0.1260 g

Percent fat in
chips

31.63 %

3.787 %

Mass of chips
Mass of beaker
+ fat
Mass of empty
beaker

A simple calculation will allow you to determine if you fat content agrees with
that reported by the manufacturer. The mass of potato chip is mostly fat,
carbohydrate, water, and protein. Assuming the water content is low, use
the information from the chip package to perform the following calculation:
Regular
Baked
Fat Content (grams):
__10.00 g______________2.000
g________
Carbohydrate Content (grams):
g________

__15.00 g______________23.00

Protein Content (grams):


g________

__2.000 g______________2.000

Total (grams):
g______

__27.00 g_______________27.00

Percent Fat from Package =


%_______________7.407 %_____

__37.04

Do your results agree? If not, why not?


Both types of chips were only a few percentage points off, about
4.000% for regular and 2.500% for baked. The differences in fat
concentration resulted from errors in measurements or errors while
extracting the fat.

DISCUSSION QUESTIONS
1. What can you conclude about low-fat products from your analysis?
The carbohydrate content in low fat chips become fat and oil in
regular chips. This reaction probably happens when the potatoes
are fried in oil.
2. Potatoes are naturally low in fat. Where does the fat come from?
Potato chips are fried in oils and fats, which makes chips
unhealthy.
3. What do chemists mean by extraction?
The removal of a part, usually a specific part or element, of the
molecule from the rest of the molecule.

Part 2: Examining solvent polarity by Thin-layer


Chromatography
Qualitative Interpretation of your TLC Plate
Did the known pure substances each produce a single spot? Did these spots
move different distances?
Yes, each pure substance moved to a single spot on the plate and
stayed in a concentrated area.
Rf Values
Calculate the Rf value for each spot, and report in the table below.
Sample

Aspirin

Label on
TLC Sheet
1

Distance to
Center of
Spot

Distance to
Solvent
Front

4.300 cm

4.500 cm

Calculated
Rf
0.9600

Acetaminop
hen

3.100 cm

4.500 cm

0.6900

Ibuprofen

No data

4.500 cm

No data

Caffeine

3.400 cm

4.500 cm

0.7600

Unknown
#3

3.400 cm,
4.100 cm

4.500 cm

0.7600,
0.9100

How many spots did your unknown produce? Can you identify which
compounds are present?
The unknown produced 2 spots, which were closest to aspirin and
caffeine. Caffeine had the same Rf, while the second sample traveled
0.2000 cm less than aspirin. This suggests that aspirin and caffeine
were present in the compound because the 2 dots produced by the
compound traveled the same distance as aspirin and caffeine.
Draw (or upload) a picture of your TLC plate below.

Note: ibuprofen did not leave a dot anywhere on the plate, which prevented
data from being gathered for this sample.

DISCUSSION QUESTIONS

1. What would be the advantage or disadvantage of using a taller TLC


sheet?
If capillary action allows the solvent to move that far, the taller
sheet would allow the samples to separate more, but would also
take more time.
2. From your results, predict the relative polarity of the pure compounds
you used. Can you justify your answer based on the molecular
structures shown below:

Aspirin
Caffeine

Acetaminophen

Ibuprofen

Aspirin is partially polar because the top half has a carboxyl


group, which has a hydroxide atom, but the oxygen atoms at the
bottom pull ions back towards them.
Acetaminophen is not very polar because the oxygen and
hydrogen interaction in the hydroxide molecule make it polar,
but the nitrogen also attracts ions and balances the polarity of
the molecule.
Ibuprofen is very polar because it has a hydroxide in a carboxyl
group on the same end, which pulls electrons towards them,
though this cannot be proven based on the chromatography
data.
Caffeine is somewhat polar because the oxygen and nitrogen
atoms interact with electrons, but each pull them towards
themselves to spread out the polarity.
3. If two compounds have the same Rf, do they necessarily have the
same structure? Justify your answer.
Not necessarily. Although there was no result for ibuprofen in the
chromatography and thus makes it difficult to compare the other
groups (it is possible it could have the same Rf as another
molecule), compounds can be very different. For example, if the
location of just one oxygen atom is changed in aspirin, it would
most likely travel a very different distance, not to mention
becoming a different molecule.

CONCLUSIONS
In this lab, students experimented with chromatography and extraction
of fat. In the fat extraction portion, the percentage of fat in my potato chip
sample was representative of the actual nutrition information found on the
label. My value of regular chips was 31.63%, only 5.410% away from the
actual percentage, which is 37.04%. My value of the baked chips was
3.787%, off by 3.620% from the official value of 7.407 %. These errors could
have been caused by improper measurements or procedural errors. For
example, when extracting the solvent from the fat on the hot plate, too much
or too little might have been extracted from the mixture and would have
affected the remaining amount.
In the chromatography section, I determined that unknown #3
contained aspirin and caffeine because of the Rf and distance traveled. Rf
values were the same for caffeine, and aspirin was off by 0.2000 cm, but that
is a small difference. These samples moved because they were polar and
interacted with the paper. The more polar they were, the less they moved
because they interacted more with the paper. Therefore, the most polar
molecule is caffeine and the least polar is aspirin. Ibuprofen did not show any
sign of action. There was no dot on the starting line, nor anywhere on the
plate. I confirmed with other students in the lab, and they did not achieve
any results with the ibuprofen sample either. This might be because the
ibuprofen sample was ineffective and simply did not interact with the plate.
Avoiding errors in future recreations of this experiment can be done by
ensuring that all samples are pure and effective. This will ensure that the
experiment can be done without unexpected errors.

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