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216%20F06-E1 - Page 2 Name I(4 points Arrange the following...

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solvent front II . (9 points) Silica gel thin layer chromatography (TLC) is often used to monitor the progress of an organic reaction. For the following ester hydrolysis reaction, a solvent system is selected to give the starting material an R f value of about 0.5. (1) Provide in the box below the structure of the expected product 6 . (2) Fill in the spots that would be expected when the reaction is 50% compete and 100% complete, each after acidic work-up. Make sure to assign each spot you draw to the corresponding compound number ( 5 , 6 , or 7 ). Consider only the compounds that can be visualized as a spot on TLC upon exposure of each solvent-dried plate to a 254 nm-UV lamp. Name _____________________________ On each TLC plate, a student has placed a sample of the starting material ( 5 ) as a reference on the left of the plate, a spot of the reaction mixture (after acidic work- up) on the right, and a co-spot in the center of each. Co-spotting is where some of 5 and some of the reaction mixture are spotted together in order to make better comparisons. 50% completion co-spot reaction mixture co-spot reaction mixture 100% completion 5 I . (4 points) Arrange the following four compounds in order of their R f values when analyzed by thin-layer chromatography (TLC) on silica gel-coated plates using CH 2 Cl 2 as the developing solvent. No partial credit
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