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Name: ________________________________

Lab (Day & Time):__________________

Worksheet2: Thin Layer Chromatography

Part (I): Predict the relative polarity and trend in Rf values of Tylenol, phenacetin and acetanilide based on their
structures.
Complete the following table by examining the structures of the three compounds. Draw the structures of the
three compounds, one at a time, in the interactive PSA calculator (link below) to obtain the computed value of
polar surface area.

http://www.molinspiration.com/services/psa.html

Structure # of H-bond # of H-bond Total # of H- Polar Surface
donors acceptors bonding sites Area (Å2)
Tylenol





Phenacetin






Acetanilide







1. Based on the total number of hydrogen bonding sites, which compound is expected to interact more strongly
with the silica stationary phase?



2. Based on the polar surface area, which compound has the highest polarity?




3. Arrange the three compounds in the order of increasing Rf values. Briefly rationalize your prediction.

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Part (II): Optimize a mobile phase to analyze the standard samples of the three compounds by thin layer
chromatography. (Make sure that you supply the relevant units where applicable.)

TLC 1: Composition of mobile phase (% of each component): ____________________

Volume of hexanes __________________ Volume of ethyl acetate ________________________

Distance travelled by the mobile phase: ___________________

Distance travelled Rf TLC Sketch
Tylenol




Phenacetin




Acetanilide







TLC 2: Composition of mobile phase (% of each component): __________________

Volume of hexanes _______________ Volume of ethyl acetate ____________________

Distance travelled by the mobile phase: ___________________

Distance travelled Rf TLC Sketch
Tylenol




Phenacetin




Acetanilide

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TLC 3: Composition of mobile phase (% of each component): __________________

Volume of hexanes _______________ Volume of ethyl acetate ____________________

Distance travelled by the mobile phase: ___________________

Distance travelled Rf TLC Sketch
Tylenol




Phenacetin




Acetanilide







TLC 4: Composition of mobile phase (% of each component): __________________

Volume of hexanes _______________ Volume of ethyl acetate ____________________

Distance travelled by the mobile phase: ___________________

Distance travelled Rf TLC Sketch
Tylenol




Phenacetin




Acetanilide










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Part III: Identification of the organic component in the unknown

Composition of the optimized mobile phase: _________________________________________________

Based on your observations in Part (II), briefly justify your choice of this solvent system.









TLC analysis:

Distance travelled by the mobile phase: ___________________

Distance travelled Rf TLC Sketch
Tylenol



Phenacetin



Acetanilide



Unknown





Results:

Identify the ingredients of the unknown mixture provided to you based on the TLC analysis? Explain how you
arrive at your conclusion.