Organic Chemistry Lab 344 synthesis of isopentyl acetate (banana oil)

Organic Chemistry Lab 344 SYNTHESIS OF ISOPENTYL ACETATE (BANANA OIL) + * OH + HO CH,02 C 8H:20 MW:60.05 MW.88.15 d: 1.049 g/mL d: 0.809 g/mL BP: 110°C BP: 130°C C7H1402 MW:130.19 d: 0.876 g/mL BP: 142°C + H:0 H2O MW:18.02 d: 1.0 g/mL BP: 100°C IIIIIII on the lower us e st Do not combine with the ances From step 4. The acidic laver from form CO all react with the basic layer from this step to 8. Wash the upper organic e layers well and allow them to separate. with 10ml of sodium bicarbonate. Mix the 9. Drain off the lower a cous verandbine with the queous layer from step 7 10. Drain the upper canicher into a dean Erlenmeyer flask 11. Add a small amount of a budous sodium sulfate 105-10 to the organic layer and Swirl well to remove any remaining water. 12. Decant the organic layer into a pre welghed 100ml RB Rask. 13. Remove the ether solvent on the ratio Dorot allow the water bath on the rotovap to get above 30°C or you will lose product! 3.999 product 14. Weigh the product and calculate the percent yield of the crude product. 15. Dispose of the aqueous layers from Steps 4,7 and 9 in the aqueous waste container, Pre reading Text: Experiment 12, pp. 81-84 Day One: Reaction: Day Two: Distillation: 1. Assemble a reflux apparatus using a 100 ml of round-bottom flask with a magnetic stirring Claisen Head, thermometer and a water condenser 2. Use a heating mantle as the heat source and a magnetic stir plate for stirring. 3. Add 5.0 ml of isopentyl alcohol to the 100ml flask 4. Add 7.0 mL of acetic acid to the 100ml flask. 5. Carefully add 5 drops of concentrated sulfuric acid to the round bottom flask in a dropwise fashion using a pipette. NOTE: It is very important to add the reagents in the PROPER order. 6. Reattach the condenser and turn on the water to circulate through the condenser 7. Heat the solution to reflux (ca. 110ºC) and then hold at reflux for 60 minutes. 8. After refluxing, remove the heat source and allow the apparatus to cool to almost room temperature 1. Set up a gimple distillation using a magnetic stir plate for stirring and a heating mantle for heating. Be sure to have a magnetic stirrer in your flask with your crude product from Day 1 step 15). A 100ml RB flask is best for the distillation pot. 2. With good sting and gentle heating gradually beat the reaction flaskuntil your product begins to boil while observing the distillation temperature as trises 2. At first a "forest will be collected of lower boiling (<140°C) impurities in your product Collect the forecut in a small pre-weighed" Erlenmeyer flask. Report the amount of forecut that was taken, 4. When the distillation temperature reaches 140°C, collect your product in a clean pre weighed Erlenmeyer flask. Continue distilling until only 1-2 drops of liquid remains in the destilling flask Record the observed boiling point range in your notebook - 1.3 5. Obtain a weight of your distilled product and report the percent yield.) 6. Obtain an IR spectra of your product using salt plates. Identify the following peaks on the (CO, CH, C-O). Is any acetic acid detected (O-H peak]? Extraction: 1. Add 10 ml of diethylether to the 100ml flask. Stir well. 2. Add 10mL of water to the 100ml flask. Stir well. 3. Transfer the mixture to a separatory funnel and allow the layers to separate. Drain off the lower acidic aqueous layer and set aside. Carefully add approximately 10 ml of 5% sodium bicarbonate to the separatory funnel dowly. NOTE: you will observe some gas bubbles (Cozwi. Mix the layers well in the separatory funnel and then allow them to separate.