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1. Mobile Phase: the phase the moves; can be gas or liquid (solvent; eluent)
For liquids, the polarity of a solvent is defined as its ability to dissolve polar
organic compounds.
Compounds dissolved into the solvent spend more time moving in the mobile
phase
Non-polar solvents can only dissolve non-polar compounds.
As the relative polarity for solvents increases, the solvents will be able to
dissolve more compounds, beginning with the non-polar ones and then increasing
numbers of more polar ones.
Very polar solvents will be able to dissolve ALL compounds.
For Chromatography: Polar Dissolves More not like dissolves like
Some Common Solvents: (listed by increasing polarity)
Petroleum ether (C5 isomer compounds, like pentane; not a true ether)
Ligroin (C6 isomer compounds, such as hexane)
Diethyl Ether (CH3CH2OCH2CH3)
Dichloromethane (CH2Cl2)
Ethyl Acetate (ester: CH3CH2OC(O)CH3)
Methanol (alcohol: CH3OH)
Acetic Acid (carboxylic acid: CH3CO2H)
And of course mixtures of the above solvents can be used.
Consider the following example: Compound A is a non-polar compound and compound
B is a polar compound.
Add Petroleum ether (non-polar!) Which will dissolve?
Only Non-Polar A
Add Diethyl Ether (more polar!) Which will dissolve?
Both!
1
In todays lab, well begin the separation for column chromatography with
petroleum ether and only remove the non-polar compound. We will then switch to a
more polar mixture of petroleum ether and diethyl ether to remove a more polar
compound.
If we used the more polar mixture first, what problem would occur?
Both compounds would travel down the column at the same rate because both are
dissolved in the more polar mixture. No separation!
2. Stationary Phase Alumina or Silica on a solid support
The more polar the compound, the stronger the compound adheres (sticks) to
the adsorbent.
Silica Gel (SiO2) and Alumina (Al2O3) are the two most common adsorbents for
separations in the organic lab.
Functional Groups (listed by increasing polarity):
Alkanes
Alkenes, alkynes and aromatics
Ethers (R-O-R)
Esters (RCO2R
Ketones and aldehydes (RC(O)R or RC(O)H)
Amines (:NR3)
Alcohols (ROH)
Carboxylic Acids (RCO2H)
Partitioning Effect:
Generally, polar compounds spend more time on the stationary phase (stuck) and
non-polar compounds spend more time in the mobile phase (moving in the solvent).
The goal is to use a solvent system that only moves the least polar compound, until
it is completely removed from the system. Then a more polar solvent can be added
to move the next compound.
Column Chromatography:
Sand
alumina
or silica gel
Sand
Packing of the Column: -demo Must remove air bubbles pockets of air allow compounds to travel in the
mobile phase faster through air pockets resulting in separation that is not
uniform
Column must be assembled in a vertical fashion, so bands will travel downwards
in an even and uniform fashion for the best separation
Sample must be loaded in the most concentrated method in order to start with
the narrowest band possible for best separation
3
o wide bands tend to stay wide (or get wider) and overlap
Developing Chamber
and Cover
-solvent in bottom
-add a "wick"
Microcapillary Tube
TLC can also be used to check the purity of a compound. A pure compound will
always appear as a single spot (because it is a single compound) regardless of what
solvent system is used for developing the plate. The solvent system should be
neither very polar nor very non-polar when checking this. This should result in an
Rf value in the range of 0.2-0.8, ideally. Non-polar solvents would not move the
spot enough and polar solvents would move them too much to be able to evaluate.
Pure or Not?
6
non-polar
solvent
polar
solvent
OH
LiAlH4
The starting compound is spotted on a TLC plate with the reaction mixture, at
timed intervals to monitor the progress. The reaction SHOULD show a decrease in
the starting material and an increase in a new MORE POLAR compound spot.
x
sm
x
rxn
T = 0 min
x
sm
x
rxn
T = 15 min
x
sm
x
rxn
T = 30 min
x
sm
x
rxn
T = 45 min
x
sm
x
rxn
T = 60 min