Lab 3: Thin Layer Chromatography Conclusion The objective of this lab was to understand the use of thin layer

chromatography, which demonstrates aspects of polarity and identifying unknowns. When looking at the crystals of the unknown sample, one can predict/ conclude, even before the test is started, that Fluorene is present since the crystals were white, but not like the beadlike form of other compounds. The TLC plate is covered with the polar substance of silica gel. The silica gel then allowed the non-polar substance methyl chloride to travel up the plate. The methyl chloride in turn carried the fluorine, 9-fluorenone, and 9-fluorenol, and the unknown substance up the TLC plate according to their polarity. The flourenone traveled with the methyl chloride the whole way up the plate indicating that fluorene was non-polar, since like dissolves like. The 9-fluorenone moved up the plate, but not as far as fluorene, indicating that 9-fluorenone is more polar than fluorene. The 9-fluorenone is more polar than fluorene. The 9-fluorenol moved up the plate the least, indicating that it was the most polar substance. The reason why non-polar substances move up the plate farther than polar substances lies in hydroxide (OH-) on the silica gel. A polar substance contains a charge which the hydroxide is attracted to, causing friction because hydrogen bonding occurs. The stronger the charge on the substance, the more friction occurs, and the less the substance moves up the TLC plate. From this experiment, one could see that 9-Fluorenol had the highest charge. 9-Fluroneone had a slight charge and fluorene most likely had no charge (by its behavior display in the lab) since it travelled the same as the methyl chloride. The unknown was determined to be made of 9-Fluorenone and fluorene because it contained the Rf value of 0.94, which was also fluorenes and the Rf value of 0.78, which was also 9-Fluorenones. The Rf value of 9-Fluorenol was 0.36, which the unknown substance did not contain.

Post-Lab
1. Contrast liquid/liquid extraction and TLC TLC is based on polarity. In the liquid/liquid extractions, one can isolate a compound from a mixture with TLC; one cannot isolate a compound, but can identify what compounds are in an unknown. 2. What are the polar and non-polar phases in TLC? The polar phase was the silica gel, while the non-polar phase was the methyl chloride. 3. Suppose you were visualizing a TLC plate and all the spots were at the solvent front. How

could you remedy this problem? One could remedy this problem by taking a new TLC plate and let the sample spots dry completely before sticking it in the methyl chloride, that way there is no mobile phase for the compounds. Another way is to use higher concentrations of the solvents. 4. How could TLC be used to analyze the progress of a chemical reaction?
TLC could be used to analyze the progress of a chemical reaction by testing for changes in polarity only if a reaction causes a change in polarity though. To do this, one could first test the starting materials on a TLC plate to a new TLC plate, different times as the reaction progressed to see when the mixture switches from polar to non-polar, or vice versa. Additionally, one could use an elution mixture to separate all the products of the experiment. After a complete reaction occurs, then one could do a final TLC plate to see if all the starting materials went to product. 5. Name and explain to other types of analytic techniques used in organic chemistry.

Another type of analytical technique used is gas-chromatography, which is very similar to TLC. Gas chromatography can identify the same aspects of chemicals in a mixture as TLC. The difference is gas-chromatography uses a gas, while TLC uses a liquid. Also, another type of analytical technique that could be used is crystallography. This involves analyzing the deflections of X-ray beams off molecules.