Expierement 4 - 10 4 bc497f4cceb7453bb7628f531f30f669

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University of Maryland, Baltimore County *

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351L

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Chemistry

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Jan 9, 2024

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Expierement 4 - 10/4 1 Expierement 4 - 10/4 1. Calculate the R values for your unknown and for each reference sample. Based on the R value, identify your unknown. Did you get the same R value for both runs of your unknown? If not, comment on the possible reasons for the difference. Rf = Distance traveled by the spot / Distance traveled by the solvent Aspirin - Rf = 2.1cm / 5cm = 0.42 Acetaminophen - Rf = 1.5cm / 5cm = 0.30 Ibuprofen - Rf = 3.2cm / 5cm = 0.64 Caffeine - Rf = 0.8cm / 5cm = 0.16 Unknown 1 - Rf = 1.5cm / 5cm = 0.30 Unknown 2 - Rf = 1.5cm / 5cm = 0.30 I obtained the same values because the same substance was used repeatedly in the test. 2. Comment on the most challenging part of this experiment for you. What would you do differently if you had the chance to repeat this experiment? There was nothing exceptionally difficult. I had difficulty positioning the paper in the chamber correctly so that it was at an angle and allowed the solvent to travel up the paper. If it was placed the wrong way, it would cause uneven spreading of the solvent and the spots would not develop correctly. 3. Suppose you run TLC of the reaction mixture using dichloromethane/methanol (1:1) as an eluent. TLC shows one spot with an Rf value of 0.98. Does it mean that the given mixture contains only one component? Why or why not? What specifically would you change in the conditions for running TLC to obtain more accurate information about the contents of the mixture? The presence of only one spot with an Rf value of 0.98 does not necessarily mean that the mixture contains only one component. It indicates that the solvent used is too polar, which leads to an inaccurate measurement of the spot. When the Rf value
Expierement 4 - 10/4 2 is close to one, it means that the spot and solvent have traveled almost the same distance. Using a less polar solvent would provide a more accurate representation of the spot's travel distance. This would allow for the identification of different mixtures present on the paper. 4. Another popular analgesic is naproxen (the active ingredient in Aleve). (a) Look up and draw the structure of naproxen. (b) Suppose you carry out a TLC separation of phenacetin, acetanilide, and naproxen (refer to experiments 2 and 3 for the structures of acetanilide and phenacetin) on silica gel. Rank these three compounds from the one with the highest Rf to the one with the lowest Rf. Since silica gel favors less polar structures, the compound with the highest Rf value would be Naproxen, followed by acetanilide, and then phenacetin. Phenacetin is the most polar due to the presence of oxygen atoms and functional groups. Acetanilide has functional groups and oxygen, making it less polar than phenacetin. Naproxen is the least polar, with only the presence of oxygen. The highest Rf value indicates the compound that travels the furthest. Since Naproxen is the least polar, it will travel further and have the largest Rf value. Phenacetin, being more polar, is less likely to move because silica gel favors non-polar compounds, resulting in the lowest Rf value.
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