Experiments that focus on extracting pigments from plants have long been

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1 Extraction and Thin-Layer Chromatography of Chlorophyll A and B from Spinach Adapted by R. McLaughlin and K. Masters from Griffin, G. William; Quach, Hao T.; Steeper, Robert L. J. Chem. Ed. 2004, 81, ; revised 12/6/04 Introduction Experiments that focus on extracting pigments from plants have long been popular in student chemical laboratory courses. These types of experiments are useful for teaching students about the techniques involved in thin-layer chromatography (TLC) because they provide a number of colorful pigments that students can easily observe and study. In this experiment, we will learn TLC techniques by analyzing pigments extracted from spinach. Prelaboratory Exercise Cautions 1. What is the purpose of the MgSO 4 in the ground spinach mixture? 2. Why should you not mark TLC plates with ink? 3. Answer PreLab questions in chapter 6 of the Lab Guide. This experiment does not involve any chemicals that are significantly hazardous. However, remember that substances used in the laboratory are never to be eaten. Be sure to properly handle and dispose of all solvents and reaction mixtures. Procedure Thin-Layer Chromatography (TLC) Solvent Preparation Prepare a solution of 6 ml petroleum ether, 1.6 ml cyclohexane, 1 ml ethyl acetate, 1 ml acetone, and 0.4 ml methanol. Place just enough of this solution in a TLC jar to cover the bottom of the jar. Tightly cap the jar while it is not in use. Obtain two TLC plates, and in pencil, mark a straight line across the plate 1 cm from the edge.

2 Sample Preparation Weigh out 0.5 g of fresh spinach. Combine this with 0.5 g of anhydrous magnesium sulfate and 1.0 g of sand. Using a mortar and pestle, grind the mixture until it becomes a fine, light green powder. Transfer this solid into a test tube and add 2 ml of acetone. Stir the solution using a stir bar for 2 minutes. Allow the mixture to sit for 10 minutes. The solid should settle to the bottom, leaving a green liquid layer on top. Transfer this green layer to another test tube using a pipet. Seal the test tube containing the spinach extract with parafilm when you are not using it. TLC of the Extract Spot the extract on the line you marked on one of the TLC plates using a capillary tube. For this particular experiment, you will spot across the entire pencil line you marked on the TLC plate. This will make the various components of the extract easier to see on the plate. Place the plate in the TLC jar with the pencil line right above the solution. Cap the jar and monitor the movement of the solution up the plate. When the solvent front reaches about 1 cm from the top of the plate, remove it from the jar. Mark a line for the solvent front before it evaporates. The components of the spinach extract are visible without a UV light; however, they decompose quickly. To slow the decomposition, immediately place a piece of tape over the entire TLC, and tape it in your laboratory notebook. Mark the lines you see before they are no longer visible.

3 Demetalation of the Spinach Extract Remove 100 µl of the spinach extract using a manual pipettor with a disposable pipet tip, and place it in another test tube. Weigh out 100 mg of Dowex 50WX8 H + resin, and place that in the same test tube. Allow the mixture to stand for three minutes. TLC of the Demetalated Extract Using a capillary tube, spot the liquid mixture on a TLC plate. Be careful not to get any of the Dowex resin on the TLC plate. Repeat the procedure you used for the TLC of the spinach extract. Again, the components decompose quickly so be sure to tape the TLC plate in your notebook immediately and mark the visible lines. Clean-up The ground spinach solid in the first test tube can be left to dry and then thrown away in the trash. The acetone extract solution can be diluted with water and poured down the drain. The Dowex resin solution can also be dried and then thrown away in the trash. Analysis The TLC plate of the spinach extract should reveal four pigment lines. From the bottom of the plate up, there should be a yellow line for xanthophyll, a green line for chlorophyll b, a brighter green line for chlorophyll a, and a yellow line for β-carotene.

4 You can obtain R f values for each of your pigment lines using the equation in Figure 1. R f = Distance between the starting point and pigment line Distance between the starting point and solvent front Figure 1 Equation for determining R f values The literature reports the following R f values for each component: R f = 0.16 for xanthophyll, R f = 0.32 for chlorophyll b, R f = 0.44 for chlorophyll a, and R f = 0.95 for β- carotene. The TLC plate of the demetalated extract should reveal five pigment lines. The lines for xanthophyll, chlorophyll b, and β-carotene should remain. In addition, a dark green line for pheophytin b should appear after the chlorophyll b, and an even darker green line for pheophytin a should appear after that. According to the literature, the R f = 0.49 for pheophytin b; the R f = 0.60 for pheophytin a. Final Report Discuss what happened when you demetalated chlorophyll a. 1. Several solvent systems were tried before the five solvent system used in this report. Below are the TLC plates for those systems as well as the one used in this experiment. Why was the five solvent system we used chosen? Why was the largest component of the five solvent system petroleum ether rather than cyclohexane? What would happen if you used

5 a solvent system that consisted mostly of cyclohexane instead? 2. Rank the components of the spinach extract from most to least polar. 3. Rank the components of the demetalated extract from most to least polar. 4. Answer PostLab question #3 in Lab Guide.

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