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7. Obtain the prepared and dissolved solutions containing the known compounds Ibuprofen,
acetaminophen, caffeine, and aspirin (acetylsalicylic acid).
8. Spot each of the knowns on the origin line of the first plate with the capillaries provided. The
spots should be evenly spaced at least 5 mm apart. Spotting samples too closely will lead to
smearing, which will lead to poor results.
9. Add enough ethyl acetate (containing 5% acetic acid) to a 100-150 ml beaker to barely cover
the bottom of the beaker. Build a developing chamber, as illustrated below, using a 100-150 ml
beaker and a watch glass.
10. Monitor the chamber. When the solvent travels up to within 1 cm of the top of the plate,
remove it and make a line across the solvent front. This line needs to be drawn immediately,
before the solvent begins to evaporate.
11. Repeat steps 8-10 with the other 2 plates and 6 unknowns. Run the plates separately, ensuring
you mark the solvent line each time after removing the plate from the developing chamber.
12. Once all 3 plates have been marked, look under an ultraviolet lamp. The components should
clearly stand out against the fluorescent green silica gel. Carefully circle all the dark spots seen
(there can be more than one spot per lane depending on the nature of the mixture).
III. Safety
General: All those working in an organic chemistry lab need to exhibit caution due to
boiling water, hot glassware, and potentially dangerous chemicals. Safety glasses and gloves
must be worn for the entire experiment. Handle spotting capillaries carefully as they are very
fragile and sharp. With corrosive chemicals, like acetic acid, be careful when dispensing. With
flammable chemicals such as ethyl acetate and methylene chloride, keep away from sparks, hot
surfaces, and fumes. With toxic chemicals such as methylene chloride, keep the snorkel on
throughout the lab. With any glassware, check the temperature prior to handling allow to cool
before disassembling.
Acetaminophen: Overexposure can lead to nausea and vomiting; It can damage the liver,
kidneys and central nervous system; Eye and skin contact causes irritation and redness;
also may cause respiratory irritation and hinder breathing.
Acetylsalicylic Acid: Harmful if ingested; causes serious eye irritation; may cause an
allergic reaction, induce asthma or cause trouble breathing; repeated exposure may cause
damage to organs.
Caffeine: Irritation of the skin, eyes, mucous membranes and respiratory tract; difficulty
breathing if inhaled; skin and eye contact may cause irritation and redness; toxic if
ingested in excess.
Ibuprofen: Causes serious eye irritation; skin contact causes potentially severe irritation
and redness; may inhibit breathing and cause respiratory problems; prolonged exposure
can target organs due to toxicity to blood, lungs, nervous system , and mucous
membranes.
Ethanol: Flammable and toxic; eye contact causes severe irritation and pain; ingestions
causes nausea, vomiting, dizziness, headache, drowsiness and unconsciousness.
Inhalation respiratory tract irritation and suffocation.
Methylene Chloride (dichloromethane): Can enter the body through means of
inhalation, skin absorption, ingestion, skin and/or eye contact, leading to an individual
experiencing irritation to eyes, skin; weakness or exhaustion, drowsiness, dizziness;
numbness, tingle limbs and nausea. It is considered a potential occupational carcinogen.
Ethyl Acetate: headache, irritation of respiratory passages and eyes, dizziness,
drowsiness and nausea, weakness, loss of consciousness; prolonged exposure may cause
organ damage.
Acetic Acid: Flammable liquid and vapor; harmful in contact with skin; causes severe
skin burns and eye damage; may cause respiratory irritation, coughing, and shortness of
breath.
Compound Structure Molecular Boiling point Density pKa
name weight g/mol C
Acetic Acid
Ethanol
Ethyl Acetate
Acetylsalicylic
Acid
Caffeine
Ibuprofen
Citations
"Acetic acid | CH3COOH - PubChem." National Center for Biotechnology Information. U.S.
National Library of Medicine, n.d. Web. 25 Feb. 2017.
"Aspirin | C9H8O4 - PubChem." National Center for Biotechnology Information. U.S. National
Library of Medicine, n.d. Web. 25 Feb. 2017.
"Acetaminophen | C8H9NO2 - PubChem." National Center for Biotechnology Information. U.S.
National Library of Medicine, n.d. Web. 25 Feb. 2017.
"Caffeine | C8H10N4O2 - PubChem." National Center for Biotechnology Information. U.S.
National Library of Medicine, n.d. Web. 25 Feb. 2017.
"Dichloromethane." Dichloromethane | CH2Cl2 | ChemSpider. Royal Society of Chemistry
2015, n.d. Web. 25 Feb. 2017. <http://www.chemspider.com/Chemical-
Structure.6104.html?rid=1e136cd5-fefd-4664-99a5-3153a2c56338>.
"Ethanol | CH3CH2OH - PubChem." National Center for Biotechnology Information. U.S.
National Library of Medicine, n.d. Web. 25 Feb. 2017.
"ETHYL ACETATE | CH3COOC2H5 - PubChem." National Center for Biotechnology
Information. U.S. National Library of Medicine, n.d. Web. 27 Feb. 2017.
"Ibuprofen | C13H18O2 - PubChem." National Center for Biotechnology Information. U.S.
National Library of Medicine, n.d. Web. 25 Feb. 2017.
Richard Hubbard, and Richard Morrison. "Thin Layer Chromatography: Identification of
Unknown Mixture." Modern Organic Chemistry I. N.p.: Worth, n.d. 1-10. Print.
Libretexts. "Thin Layer Chromatography." Chemistry LibreTexts. Libretexts, 16 Feb. 2017. Web.
25 Feb. 2017.