XX XX Organic Chemistry Lab 2203 011 June 2, 20XX

Experiment 11B: Natural Product Isolation: Caffeine performed on 05/30/2013 Objective: The purpose of this experiment is to extract caffeine, a purine pseudo alkaloid, from its native source, tea leaves. Ordinary tea bags will be used as the source of raw material. The experiment will be an introduction in the use of sublimation. Experimental Procedure: Experiment 11B was followed as described in Mayo, pages 229-234, with the following modifications: A complete, unopened, 2.0 g teabag, 20mL of water and 2.2 g of sodium carbonate in a 125mL Erlenmeyer flask were used to create the brewed aqueous extract instead 1.0g from opened tea bags, 10ml of water and 1.1g of sodium carbonate in a 50mL Erlenmeyer flask. Students were paired up for the setting up of regents and solutions and the initial brewing and reaction of the aqueous extract. Melting point of extracted caffeine was not taken. Did not perform the sublimation purification. T.A collected crude caffeine extract from the class and used it to perform a sublimation demonstration instead. Recovered mass for caffeine is the crude product as instructed.

Reaction Scheme:

Caffeine

Data and Results Table: Initial amount Tea 2.0g Extracted amount N/A N/A 0.042g N/A Percent Recovery N/A N/A 2.1% N/A

Sodium Carbonate 1.2ml Caffeine (crude) 18.073 N/A 4.0mL

Observations: During the first extraction some of the solution leaked due to a faulty centrifuge vial cap when I attempted to manually mix it by shaking. Some of the aqueous solution was left behind as residue on the first centrifuge vial when I attempted to move the solution to another vial. I did several methyl chloride rinses to get as much of the caffeine as possible. Some brewed aqueous extract was left behind in the beaker containing the tea bag. Used sand and cotton in a glass pipet instead of sodium sulfate to filter the organic phase solution. The crude caffeine was slightly yellow in color and was flaky when broken with a spatula. The purified caffeine was white in color and formed crystals.

Calculations: Mass of crude caffeine extracted

Mass of test tube with solid- mass of empty test tube= mass of crude caffeine 18.115g-18.073g=0.04200g Weight percent of caffeine in the original tea leaves (Weight of extracted crude caffeine/weight of tea leaves)*100=weight percent. (0.04200/2.0g)*100=2.1% Questions: 1. Why were five extractions (5 x 2 mL) with methylene chloride necessary to maximize the isolation of caffeine from the initial aqueous tea extract? Due to the partition coefficient not all of the caffeine dissolved into the methylene Chloride solution and a small portion remained in the aqueous phase. This made it necessary to do several extractions in order to make sure that all the caffeine was extracted. 2. Consider the structure of caffeine (re-draw it here), and answer the following questions from a structural perspective (hint: think intermolecular forces). Discuss structural features that would account for solubility in water. The purine shell of is polar due to one half of the shell being compose of nitrogen and oxygen and the other half nitrogen and hydrogen. This faciliates dipoledipole intermolecular interactions with water. Also, the attached hydrogen and oxygen faciliate hydrogen bonding with, respectively, the oxygen and hydrogen atoms in water molecules.

Discuss structural features that would account for solubility in methylene chloride. The methy groups attached are nonpolar and would be attraced to other non polar molecules through London Dispersion Forces. 3. Consider the overall process of extracting and isolating caffeine from tea leaves. Why is sodium carbonate necessary in this procedure? The sodium carbonates helps realease the caffine from the acids that are bound to it by creating ionic sodium salts that dissolve into the water leaving the caffaine to more readily dissolve into the methylene chloride. Would it be feasible to simplify the procedure by extracting tea leaves directly with methylene chloride? No, because the caffiene is attached to an acidic ionic complex which makes it polar. This greatly reduces its solubility in nonpolar solutions such as methylene chloride. 4. The purification technique of sublimation was employed in this experiment. Even if you ran out of time to run it yourself, hopefully your TA provided a demonstration. How is caffeine separated from impurities during this process? The crude sample of caffaine is placed in a vacuum flask. The flask is connected to a tube with leds to a vacuum and a cold finger tube with a rubber sleeve is placed through the top. Next, dry ice is added to the tube and the vacuum is turned on in order to remove of any moisture and drop the pressure in the flask. The flask is then heated. Since the crdue sample is in a low pressure enviroment it will start to vaporize slightly below its melting point, skipping the liquid phase.

The gasous sample of caffiene then condenses onto the cold surface of the cold finger in the form of crystals. What property or properties make caffeine an ideal candidate for sublimation? Caffeine has a higher enough vapor pressure in relation to any impurities in it. The caffeine sublimates and then condenses on the cool finger while the impurities are left at the bottom. Works Cited: 1. Mayo, D. W.; Pike, R. M.; Forbes, D. C. Microscale Organic Laboratory with Multistep and Multiscale Syntheses, 5th ed.; John Wiley & Sons, Inc., 2011; pp 229-235.