Aim: To determine the polarity of a mixture that contain aspirin, caffeine, Tylenol and Excedrin by

separating the compounds through the use of thin layer chromatography and to determine the unknown
in the mixture.
Experimental:
Chemicals: Equipment:

Name Structure Physical

Acetaminophe Solid,
n (Tylenol) Filter Paper Pencil M.P UV
=
169°C
viewing
M.Wbox=
151.17
g/mol

Acetyl salicylic O Solid,

Acid (aspirin) OH M.P =
135°C
O M.W =
CH3 180
O g/mol
Excedrin Solid,
(aspirin, M.P =
Tylenol, and 168°C
caffeine) MW =
525.5
g/mol

Caffeine O CH3 Solid,

H3C N M.P =
N
238°C
O N N M.W =
194.19
CH3
g/mol

TLC Plate

Aluminu Ruler
m Foil

Procedure:
 A literature 1 procedure was
followed with the following
modifications:
1. Methanol was not used as a
solvent.

Chemical reaction/mechanism:
N/A

Reagents: acetic acid, hexane, and ethyl acetate

Setup:
Data:

Mixture 1
TLC Plate Spot Rf
Beaker Ac 72/76 mm
2 Filter Paper As 72/76 mm
Aluminum Foil Cc 27/76 mm
Cs 27/76 mm
Ts 42.5/80 mm
Tc 42.5/80 mm
Ex 1 56/80 mm
Ex 2 43/80 mm
Ex 3 19/80 mm
Uk 55/80 mm

Result:
72
Ac: =0.947
76
72
As: =0.947
76
27
Cc: =0.355
76
27
Cs: =0.355
76
42.5
Ts: =0.531
80
 42.5
Tc: =0.531
80
56
Ex 1: =0.7
80
43
Ex 2: =0.538
80
19
Ex 3: =0.238
80
55
Uk: =0.688
80

References:

Organic Laboratory Manual, Shanbhag and Veliz, pg. 32-34, Nova Southeastern University, 2012.
Post lab Questions:
1. Predict the order of polarity of the five different benzene derivatives, (benzoic acid, salicylic
acid, p-hydroxy benzoic acid, acetanilide and p-amino phenol from the least to the most polar.
Indicate why you think the order is so.
acetanilide < benzoic acid < p-amino phenol < salicylic acid < p-hydroxy benzoic acid
2. With the use of your TLC results, rank the order of polarity aspirin, Tylenol and caffeine,
from least to most polar. b. Given the functional groups on each of these, do your results
reinforce or contradict your polarity order?
Caffeine < Tylenol < aspirin
Aspirin functional groups: carboxylic acid and ester
Tylenol functional groups: hydroxyl group and amide group
Caffeine functional groups: amines and amides
My results reinforce the polarity order.