Experiment 3: Acid/base Extraction and Separation of Acidic and Neutral Substances

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1 Experiment 3: Acid/base Extraction and Separation of Acidic and Neutral Substances Introduction You will be given a mixture that contains three substances in equal amounts: benzoic acid, 2-naphthol and 1,4-dimethoxybenzene (p-dimethoxybenzene): H H CH 3 H 3 C benzoic acid 2-naphthol p-dimethoxybenzene pk a 4.17 pk a 9.5 You will separate the three compounds by taking advantage of differences in their acidity. In their neutral, covalent forms, all three compounds are soluble in a slightly polar organic solvent such as diethyl ether (CH 3 CH 2 CH 2 CH 3 ) but are fairly insoluble in water. However, benzoic acid and 2-naphthol are acidic due to their H groups and so will be converted to their ionic salt forms on reaction with an appropriate base. Use of two different bases with two different strengths allows for selective reaction of the stronger acid versus the weaker acid. The weaker base, sodium bicarbonate, is strong enough to react with the strong acid, benzoic acid, but not strong enough to react with the weaker acid, 2-naphthol. The sodium salt that forms is ionic, highly polarized and soluble in water. Therefore a neutral compound dissolved in ether can be extracted into an aqueous base if the base is strong enough: H water-soluble! H HC 3 (aq) H CH 3 CH 3 still soluble in ether H 3 C H 3 C A stronger base, sodium hydroxide, is required to react with the less acidic 2-naphthol. The remaining two-component mixture in the ether layer can then be separated:

2 H H (aq) water-soluble H 3 C CH 3 H 3 C CH 3 still soluble in ether Note that 1,4-dimethoxybenzene does not have any acidic proton and cannot react with either base. Diethyl ether and water (think water whenever using aqueous solutions ) do not dissolve well in each other ( immiscible ) and will form layers in a container with the less dense liquid floating on top of the denser one. The piece of equipment that is used for separating these layers (or more generally, for doing liquid-liquid extractions ) is called a separatory funnel (or sep funnel ). nce all of the compounds have been separated, the neutral compounds may then be recovered as solids by adding a strong acid to the aqueous solutions of the sodium salts, causing them to precipitate from the aqueous solution in separate flasks (neutral organic compounds are no longer highly polarized and generally not soluble in aqueous solutions): Flask 1: HCl (H + ) H water-soluble not water-soluble H Flask 2: HCl (H + ) water-soluble not water-soluble The neutral, non-acidic compound that remains in the ether solution can be isolated as solid by simply allowing the ether to evaporate. All three compounds may be purified by recrystallization and their identities confirmed using melting point analysis. Pertinent information about the chemicals you are using: 2

3 MW (g/mol) MP (ºC) BP (ºC) Density (g/ml) benzoic acid N/A N/A 2-naphthol N/A N/A 1,4-dimethoxybenzene N/A N/A diethyl ether water % sodium bicarbonate (aq) 5% sodium hydroxide (aq) Conc. Hydrochloric acid methanol FR YUR SAFETY 1. Concentrated hydrochloric acid is corrosive and an irritant. Avoid skin contact by wearing gloves and, as always, goggles must be worn. In case of contact with skin, wash thoroughly with running cold water immediately. 2. Sodium bicarbonate solution will exothermically produce C 2 gas when mixed with acid. Acid must be added cautiously to such solutions to control the reaction. Also, this will cause a pressure build-up in a closed container such as a stoppered separatory funnel. Frequent venting of the pressure is required to prevent uncontrolled pressure release. PRCEDURE, WEEK NE: Separating your three compounds 1. Weigh out approximately 3 g of the solid mixture and transfer it to a 50 ml beaker. Record the exact mass used in your notebook. 2. Set up your separatory funnel Use an iron ring clamped to the metal lattice on the bench, to support your separatory funnel. Make sure the stopcock is closed and place an Erlenmeyer flask underneath the stem, in case it leaks. 3. Add 30 ml of diethyl ether to the beaker containing your mixture, and stir gently with a glass stirring rod to dissolve the solids. nce it is all dissolved, carefully transfer the mixture to your separatory funnel (don t spill it!). Add another 5 ml of ether to dissolve any remaining solids stuck to sides of beaker and transfer the dissolved remnants to the separatory funnel also. 4. Add 10 ml of deionized (DI) water to the separatory funnel you should see two layers. (Which is the aqueous and which is the organic (ether) layer?) Then add 10 ml of the 10% sodium bicarbonate solution to the funnel. 5. CAUTIN: When the bicarbonate solution is mixed together with the ether layer, C 2 gas will be generated causing a pressure buildup in the funnel. You must vent the funnel frequently as demonstrated by your instructor to release the pressure. Place the stopper in the funnel and then, while holding the stopper tightly, carefully invert the funnel several times. Immediately vent the funnel while the stem is pointing upwards and away from you (and other students) by opening the stopcock. Close the stopcock and repeat the process 3

4 several more time, venting the pressure each time until no more C 2 is given off. The goal is to get the two liquid layers to mix well enough so the solutes can freely move into the phase in which they are most soluble. You NEED to thoroughly mix the layers to ensure the base reacts with the intended acid to form the necessary salt! 6. Place the separatory funnel back in the iron ring stand, remove the stopper, and allow the layers to fully separate. nce separated, drain the lower layer into a 125 ml Erlenmeyer flask. Label this as Flask 1. Repeat the extraction sequence again on the organic layer remaining in the separatory funnel using an additioal 10 ml of 10% sodium bicarbonate solution. Drain this new aqueous extract (bottom layer) also into Flask 1. (What organic compound(s) did you remove from the mixture with this first base extraction?) 7. To the separatory funnel containing the organic layer, now add 10 ml of 5% aqueous sodium hydroxide solution. With the stopper in place, shake the mixture thoroughly, venting the pressure frequently as before. Replace the funnel in the stand, remove the stopper, and drain the lower layer into a clean 50 ml Erlenmeyer flask. Label this flask as Flask Repeat the extraction sequence of Step 7 on the organic layer remaining in the separatory funnel using an additional 10 ml of 5% sodium hydroxide solution. Drain the new aqueous extract (bottom layer) also into Flask 2. Be sure to completely drain the bottom layer without draining any of the top layer on this last separation. (What organic compound(s) did you remove from the mixture with this second base extraction? What organic compound(s) is/are left behind in the ether layer in the separatory funnel?) IMPRTANT: If attempting to complete the entire lab in a timely fashion, you will need to multi-task in steps Do not just wait to complete one step before moving on to the next think about how you may use your time in the most efficient manner. Isolating the solid in Flask 1 (Compound 1): 9. Take a clean, empty sample vial to the hood, add 5-6 ml of concentrated hydrochloric acid to it and return to your bench. This will be your acid supply for acidification of both Compounds 1 and 2. Cautiously add the concentrated hydrochloric acid drop-wise, to Flask 1, with careful stirring, using a glass stirring rod, the solution is strongly acidic (ph = 1). To test the ph, stir the solution, pull the glass rod out of the solution and tap the wet end of the rod to the surface of the ph paper. Never dip the ph paper into your solution or it may discolor your product crystals. nce acidified, make an ice bath in a large beaker, and place Flask 1 in the ice bath to ensure maximum precipitation of the solid, approximately 5-10 minutes. 10. Set up a clean Büchner funnel for vacuum filtration and isolate the solid formed in Flask 1. Wash the solid on the filter funnel with 2-3 ml of ice-cold water and then pull air through the solid for at least 5 minutes to dry it. 11. Label a small clean, dry beaker as Compound 1 and weigh it, empty. After air-drying the crystals on the Büchner funnel (step 10), transfer the solid to this pre-weighed beaker and store this beaker in your locker until you recrystallize the solid in the next lab period. Isolating the solid in Flask 2 (Compound 2): 4

5 12. Add concentrated hydrochloric acid to Flask 2 drop-wise with careful stirring, using a glass stirring rod. Use ph paper to test when the solution is acidic (ph = 1). Tap the end of the stirring rod to the ph paper don t dip the paper! nce acidified, make an ice bath in a larger beaker, and place Flask 2 in the ice bath to ensure maximum precipitation of the solid, approximately 5-10 minutes. 13. Set up a Büchner funnel for vacuum filtration and isolate the solid formed in Flask 2. Wash the solid on the filter funnel with 2-3 ml of ice-cold water and then pull air through the solid for at least 5 minutes to dry it. 14. Label a small clean, dry beaker as Compound 2 and weigh it, empty. After air drying the crystals on the Büchner funnel (step 13), transfer the solid to this pre-weighed beaker and store this beaker in your locker until you recrystallize the solid in the next lab period. Isolating the solid in the ether layer (Flask 3/Compound 3): 15. Pour the ether layer that remains in the separatory funnel out the top of the separatory funnel into a clean 50 ml Erlenmeyer flask carefully, making sure to not let any water droplets fall into the Erlenmeyer flask. Label this as Flask 3. Add about 2 g of anhydrous magnesium sulfate (MgS 4 ) drying agent to the ether extract, swirl for a minute or so, and leave the flask to sit for at least 5 minutes. 16. Label a small clean, dry beaker as Compound 3 and weigh it, empty. Filter the ether solution from Flask 3 using a short-stem glass funnel and fluted filter paper into the small beaker, to remove the magnesium sulfate drying agent. btain 5 ml of ether from the hood and use to rinse the drying agent and filter paper, to ensure all organic compounds have been completely transferred to beaker containing Compound 3. Take the beaker to a hood (designated by your instructor) and use a piece of thick walled tubing, attached to a compressed air line, to gently evaporate off the ether. A solid should form impure Compound 3. nce all ether appears to be gone, place this beaker in your drawer to store until next week Why do we need to dry the ether layer? Even though water and ether appear to be immiscible, a small amount of water is soluble in the ether and will be left behind to contaminate the solids when the ether evaporates. A solid drying agent such as magnesium sulfate absorbs the water and can be filtered off, allowing for easy removal of the water. PRCEDURE, WEEK TW: Recrystallizing your compounds Compound 3: 17. Set up a boiling water bath with ~100 ml of water (don t forget boiling stones) on a hot plate start with the hot plate setting at 4. As the water heats up, begin with the recrystallization of Compound 3, recrystallizing from a mixture of water and methanol (bp 64.7ºC). Scrape the solid from the walls of the beaker using a spatula and add 15 ml of hot (but not boiling) water. Place the beaker on the hot plate. btain 16 ml of methanol from the hood and return to your bench. Then add methanol slowly, drop-wise, with a Pasteur pipette until the entire solid just dissolved; this is known as a mixed solvent recrystallization. You will probably observe the formation of oily-like droplets in the hot solution (known as oiling out ). Continue adding methanol and swirling the beaker on the hot 5

6 plate until all of the oil droplets dissolve to give a clear, homogeneous solution. If there are any undissolved solids (insoluble impurities) in your sample, perform a hot gravity filtration using fluted filter paper; otherwise, remove the beaker from the hot plate and allow it to cool slowly to room temperature before placing it in an ice water bath. If your water supply is not boiling/steaming hot, turn up the hot plate setting to 4.5 for use in your recrystallizations of the other compounds. 18. Clean and set up a Büchner funnel for vacuum filtration and isolate the crystals of purified Compound 3. Label the Büchner funnel as Recrystallized Compound 3. Allow the compound to dry until next week. Compound 1: 19. Recrystallize Compound 1 from boiling water as you did in Experiment 1 this semester. Dissolve the compound in the minimum amount of boiling water, beginning with 10 ml of hot water and slowly adding more water using a disposable pipette (this may take ~30 ml of hot water so don t do this drop-wise!) and then add an extra pipette full of water. If there are still some insoluble impurities, perform a hot gravity filtration through fluted filter paper into a clean Erlenmeyer flask. therwise, allow the flask to cool to room temperature and then in an ice water bath until crystallization is complete. 20. Clean and set-up a Büchner funnel for vacuum filtration and isolate the crystals formed from Compound 1. Label the Büchner funnel as Recrystallized Compound 1 and allow the compound to dry until next week when you will obtain the mass and the melting point. Compound 2: 21. If desired/required, recrystallize Compound 2 from boiling water (~45 ml) following Steps Label the Büchner funnel as Recrystallized Compound 2. Allow the compound to dry until next week. PRCEDURE, WEEK THREE: Weights and Melting Point Analyses of Purified Compounds 22. Measure the masses and melting points of Compounds 1-3. For the melting points, perform a simultaneous slow run with a sample of each recrystallized compound in a separatory capillary tube using the following Digimelt Settings: START temp: 50ºC, RAMP RATE: 2ºC/min, STP temp: 140ºC. nce the first compound melts, you may stop the run and reset your START temp to 110ºC, to save time. 23. Submit all three compounds separated/purified in properly labeled vials to your instructor. CALCULATINS: Calculate the percent recovery of each compound assuming that the mass of your original sample is made of equal masses of each individual compound (i.e. if you used exactly 3.3 g of the mixture, then you started with 1.1 g of each compound.) 6

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