Lab 1 Recitation

Thin-Layer Chromatography

Key Point Summaries

Grading!!!

Key Point Summaries

Start with lab lecture notes! Then compare to
procedure/results
Practice good scientific writing
Full sentences (try), no first person, active voice, and
concise writing
It was determined that Standard II, which had an R f
value of 0.5, was a polar molecule because of its
carboxylic acid group vs. Standard II (Rf = 0.5) is
polar because of its carboxylic acid group

One page text maximum, but

Can have appendix for ChemBioDraw graphics (1 pg
max) label as Figure 1, Table 2, Mechanism 2,
Reaction 5, etc

Recitations
What will they be?
Real-life examples and applications of theory
we learned in lecture and applied in
controlled settings in lab.
May help with post-lab quiz questions

What will they not be?

Your key point summaries in spoken form.
Hi, group 2 spies!

Mandatory
Yay!

HPLC
High performance liquid chromatography
Accurate
Better reproducibility
Higher sensitivity (for smaller samples)

Informative
Multiple detection techniques could follow (UV/Vis,
mass spectrometry)

Convenient
Automatic

Image Source:
http://web.nmsu.edu/~kburke/Instrumentation/Agilent_
HPLC.gif

HPLC

Time

Less
polar

More
polar

Image Source: http://www.forumsci.co.il/HPLC/WEB-Pharm_Review/alkylphenones.gif

https://sweepingthegarden.files.wordpress.com/2013/03/spongebob.jpg
http://www.extremescience.com/images/sailfish.jpg
https://s-media-cache-ak0.pinimg.com/736x/e7/b4/cc/e7b4cc5b29da05ef80bd8b395b940bab.jpg

HPLC
High performance liquid chromatography
Accurate
Better reproducibility
Higher sensitivity (for smaller samples)

Informative
Multiple detection techniques could follow (UV/Vis,
mass spectrometry)

Convenient
Automatic

Image Source:
http://web.nmsu.edu/~kburke/Instrumentation/Agilent_
HPLC.gif

TLC before HPLC

HPLC (high performance liquid
chromatography)
Quantitative, accurate, smart
But machine column can be difficult to clean
out ($)
Not disposable

AND need lots of solvent for longer time and

labor ($$$)

TLC
Easy set-up/disposable
Image Source:
Cost effective
http://web.nmsu.edu/~kburke/Instrumentation/Agilent_
HPLC.gif
Low sensitivity but suitable for normal use

Column Chromatography
Stationary: Gel (usually polar)
Mobile: Liquid (usually not as polar)
Good for clean up (before HPLC) as well as simple
separation
Sample: Mixed compounds
Red: polar
Blue: not as polar

If all else fails

Separate using other techniques
Distillation (next week)
Extraction (the week after)
Crystallization (Chem 2321)

Food for thought

Results (high to low Rf):

Ibuprofen
Aspirin
Phenacetin
Acetaminophen
Caffeine

Can look at structure to justify results

Rf is related to polarity, and polarity is related
to structure.

Most to least polar

1. Caffeine

4. Aspirin

2.
Acetaminophen

3. Phenacetin

5. Ibuprofen

Caffeine (most polar,

lowest Rf)
Dipole-dipoles from inductive withdrawal
and resonance
Nitrogen and Oxygen can act as H-bond
acceptor

Ibuprofen (least polar,

highest Rf)
Has H-bond (polar), but has a really large
nonpolar group
Compare to other molecules

Acetaminophen,
Phenacetin
Between the two, Acetaminophen has 1
more H-bond donor (more polar)

Aspirin
Easily formed intramolecular H-bonding
limits Aspirins ability to bond
intermolecularly