All GRE Subject Test: Chemistry Resources
Example Questions
Example Question #1 : Thin Layer Chromatography
Which of the following functional groups would be expected to have the largest value during a thin-layer chromatography (TLC) experiment with an ether solvent?
Amine
Halide
Alkane
Alcohol
Alkane
The value is proportional to the affinity of the solute to the solvent. The solvent acts as the mobile phase along a polar paper stationary phase. Polar compounds will interact more with the paper, travelling slowly, while nonpolar compounds will interact more with the solvent, travelling more quickly.
A large value represents a large proclivity for the mobile solvent in the experiment. Because we are using ether, a non-polar solvent, we would expect non-polar compounds to travel the farthest on our plate. Of the answer choices, alkanes are the least polar and would thus travel farthest into the mobile phase of the four functional groups. A polar functional group, like a halide, will interact more in the stationary phase, and will thus has a significantly smaller value.
Example Question #1 : Thin Layer Chromatography
Which of the following purification techniques would best separate a nonpolar solute from a polar solute?
Distillation
Thin layer chromatography
Mass spectroscopy
Ion exchange chromatography
Thin layer chromatography
Generally, extraction is the best means of separating two solutes based on polarity. This technique allows separation based on solubility in two different solvents, which separate based on polarity.
Extraction, however, is not offered as an answer. The next best option would be thin layer chromatography. In this process, a polar stationary phase is introduced to a nonpolar solvent. Solutes are placed on the stationary phase. The nonpolar solvent acts as the mobile phase. Nonpolar solvents interact more with the mobile solvent, travelling quickly along the polar stationary phase, while polar solutes are attracted to the stationary phase and travel more slowly. This property allows for separation based on polarity.
Ion exchange chromatography is used to separate compounds with different charges, not necessarily differing polarities. Mass spectroscopy will identify compounds based on mass, and distillation will allow for separation based on differences in boiling point and vapor pressure.
Example Question #1 : Thin Layer Chromatography
Chromatography involves the separation of a mixture by allowing a mobile phase to travel along a stationary phase. In thin layer chromatography (TLC), a liquid solution is able to travel along a stationary plate. The distance that a particular compound travels compared to another compound can be determined by comparing the Rf factors for each compound. The Rf factor is determined by dividing the compound's distance by the total distance of the solvent.
Which of the following compounds would have the smallest Rf factor in a standard thin-layer chromatography (TLC) experiment?
Butanol
Hexane
Glucose
Propane
Glucose
The stationary phase in chromatography is typically attracted to the more polar compounds in a solution, while the mobile phase carried the nonpolar compounds. As a result, more polar compounds will move a shorter distance, resulting in a lower Rf factor. Glucose is a very polar molecule, and would move a shorter distance compared to the other options.
Example Question #22 : Organic Chemistry, Biochemistry, And Metabolism
A chemist carries out the synthetic scheme shown below. Unfortunately, the first two reactions are incomplete, and a mixture of compounds A, B, and C is obtained after the second step. The chemist purifies this mixture by normal phase chromatography, using silica gel as a stationary phase and a 10:1 hexanes-diethyl ether (v:v) solution as an eluent. In what order would compounds A, B, and C elute off the column?
For each choice, the first compound to elute is listed first.
B, C, A
A, C, B
B, A, C
C, A, B
C, B, A
C, A, B
In the normal phase chromatography system described, the most nonpolar compound would elute first and the most polar compound would elute last. The silica stationary phase will interact with more polar molecules, while the hexane mobile phase will carry nonpolar molecules. This would slow the progress of polar molecules as they bond to the silica, and enhance the progress of nonpolar molecules as they interact with the mobile phase.
Compound C is the most nonpolar compound because it contains only hydrogen and carbon. Compounds A and B are more polar because of the presence of oxygen, and hence the presence of polarized carbon-oxygen bonds. The alcohol group of compound B makes this compound the most polar of the three molecules by virtue of hydrogen bonding capabilities as well as the carbon-oxygen dipole. Compound B would thus elute last.
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