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Chem 26

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ANSWERS TO QUESTIONS

1. Why is the chromatogram developed in an essentially closed system?


The chromatogram is developed in as essentially closed system so that that the atmosphere inside
the chamber remains saturated with the developing solvent [1]. This is to provide the paper with equal
exposure to solvent vapors in order to ensure good chromatographic resolution. Moreover, if the
chamber isn’t covered with a lid, the solvent may evaporate and the samples may end up unseparated
near the top of the filter paper [2].

REFERENCES
[1] Pederson, S. F.; Myers, A. M. Understanding the Principles of Organic Chemistry: A Laboratory Course,
1st ed. Cengage Learning: Belmont, CA, 2011; p 128.

[2] Mohrig, J. R.; Hammond, C. N.; Schatz, P. F. Techniques in Organic Chemistry, 3rd ed. W. H. Freeman and
Company: New York: NY, 2010; p 226.

2. What are the considerations in choosing a chromatographic solvent?


In paper chromatography, certain considerations must be taken into account in selecting the best
solvent or combination of solvents to use, and it is usually determined by trial and error. First, the
solvent must be able to readily dissolve the solute but not compete with it for binding sites on the
stationary phase. If not, the individual components of the solute may remain adsorbed at the origin.
Second, the solvent should not be too polar because it may cause the solvent to have a strong attraction
to the stationary phase and it will force the solute to remain in the mobile phase. If this occurs, the
components of the solute will move rapidly up the chromatogram without establishing the solid-liquid
equilibria which is needed for separation. In addition, the mobile phase must be significantly less polar
than the components of the mixture to obtain an effective separation [3]. Third, if the nature of the
compounds to be separated is known, then the polarity of the solvent may be effectively considered.
In general, a nonpolar solvent is used for nonpolar compounds and polar solvent is used for polar
compounds. However, if not, a testing mixed solvent with a 50:50 ratio is used to see how much
separation occurs, and this can be just accordingly depending on how far the components have
separated on the filter paper [2].

REFERENCES
[2] Mohrig, J. R.; Hammond, C. N.; Schatz, P. F. Techniques in Organic Chemistry, 3rd ed. W. H. Freeman and
Company: New York: NY, 2010; p 231-232.

[3] Gilbert, J. C.; Martin, S. F. Experimental Organic Chemistry: A Miniscale and Microscale Approach, 5th ed.
Cengage Learning, Boston, MA, 2011; p 182.

3. Compare and contrast between normal phase and reverse phase chromatography.
In normal phase chromatography, the stationary phase is polar while the mobile phase is less polar
or nonpolar. As a result, the polar components of the mixture are more strongly attracted to the
stationary phase and are moved slowly than the non-polar components along the mobile phase. On
the other hand, in reverse phase chromatography, the stationary phase is nonpolar while the mobile
phase is polar. The polar components move up the chromatogram faster than the nonpolar
compounds. This is because the nonpolar components are more strongly held to the stationary phase
[1].
REFERENCES
[1] Pederson, S. F.; Myers, A. M. Understanding the Principles of Organic Chemistry: A Laboratory Course,
1st ed. Cengage Learning: Belmont, CA, 2011; p 124-127.

4. Explain how iodine crystals help to visualize the other pigments.


In some cases, the compounds that have separated are hardly visible or colorless. In order to
visualize these compounds better or make it appear distinctly in the chromatogram, visualization
reagents or methods are used. One reagent often used is iodine since it reacts with a lot of organic
compounds to form complexes that are either distinctly yellow or brown in color and this reveals the
position of the compounds in the chromatogram. The process starts when the filter paper is placed in
a closed chamber with iodine crystals that is gently warmed. As the jar is filled with the iodine vapors,
the spots appear. Once the chromatogram is removed from the iodine chamber, it has to be marked
immediately since the spots are not permanent because the iodine sublimes off the plate [4].

REFERENCES
[4] Pavia, D. L.; Lampman, G. M.; Kriz, G. S.; Engel, R. G. A Microscale Approach to Organic Laboratory
Techniques, 6th ed. Cengage Learning: Boston, MA, 2018; p 835-836.

5. Suggest one method that can be used to visualize highly conjugated compounds but are not colored.
One method that can be used to visualize highly conjugated compounds is through ultraviolet light.
If the adsorbent has fluorescent indicators, conjugated compounds absorb the ultraviolet light. Due to
this absorption and when the filter paper is viewed under an ultraviolet lamp, they exhibit as dark spots
on a colored background [1].

REFERENCES
[1] Pederson, S. F.; Myers, A. M. Understanding the Principles of Organic Chemistry: A Laboratory Course,
1st ed. Cengage Learning: Belmont, CA, 2011; p 128.

6. Given a mixture that contains the following compounds: 2-chloropentane, pentanoic acid,
cyclopentane and pentanal. Arrange the following compounds in increasing Rf if the mixture is ran using
paper chromatography with the same solvent system used in the experiment.
The ranking of the polarity of functional groups from the most polar to the least polar are as follows:
carboxylic acids > alcohols > amines > aldehydes > ketones > esters > ethers > aromatic hydrocarbons
> alkenes > alkyl halides > alkanes. Given this, the compounds in the mixture have this order in terms
of decreasing polarity, 2- pentanoic acid (carboxylic acid) > pentanal (aldehyde) > chloropentane (alkyl
halide) > cyclopentane (alkane). In the experiment, the solvent systems used were 9:1 petroleum ether
: acetone and 1:1 ethyl acetate : hexane, both of which are nonpolar. In this normal phase
chromatography, the arrangement of the compounds based on the increasing Rf values are as follows:
2- pentanoic acid < pentanal < chloropentane < cyclopentane.

REFERENCES:
[5] University of Massachusetts Amherst. Thin Layer Chromatography. Retrieved from
https://people.chem.umass.edu/samal/267/owl/owltlc.pdf (accessed Sept 6, 2019).
ssed on at 60 years old in 1997, finishing the adventure of another "lost clan."