CHEM2410 Essential Oil from Cinnamon Introduction The flavors and smells that we experience are a result of particular

chemicals or combinations of chemicals interacting with our olfactory or taste receptors. While an artificial flavor may include synthesized duplicates of some of the molecules found in the H H C C natural source, it usually lacks the complexity of flavor that C would be found if trace amounts of additional flavoring O H molecules were also included. Some spices, such as cinnamon, consist of largely one type of distinctive molecule that is responsible for the characteristic flavor and odor. In the case of cinnamon this compound is cinnamaldehyde, whose structure is shown.

cinnamaldehyde

In this experiment you will perform a steam distillation on ground cinnamon and collect the cinnamaldehyde mixed with water as an azeotrope. Extraction of the cinnamaldehyde with methylene chloride and then evaporation of this solvent will yield the cinnamaldehyde oil. By testing the reaction of your oil with bromine, the presence of the alkene can be determined. When alkenes react with bromine in this test, the dark red-brown color of Br2 will no longer be present when the bromine atoms bond to the carbons, showing that the substance contained a functional group that can react with bromine. Before you come to lab Read about steam distillation, azeotropes, and drying agents in Mohrig. Review extraction. Complete the prelab as usual including listing the physical properties and safety data on methylene chloride (also known as dichloromethane) especially the density!. Procedure You will be using a 250 mL 3-neck flask for this experiment (that must be cleaned and returned at the end of the lab period). In this flask, place 2 grams of ground cinnamon (record exact amount), 25 mL of water, and a large magnetic stirring bar. Secure this flask with a clamp and place it in a thermowell on top of a stirring plate. Add a 3-way adaptor, thermometer, and condenser as you would for a regular distillation. Put stoppers in the other 2 necks of the flask. Boil the mixture rapidly and collect about 10 to 15 mL of distillate. When you are done with the distillation, remove the flask from the heating mantle. Clean out the flask thoroughly before you return it to the instructor. Transfer the distillate to a separatory funnel and extract with 5 mL of methylene chloride. Drain the lower layer off and save it in a small Erlenmeyer flask. Add an additional 2 mL of methylene chloride to extract the upper layer again. Combine this lower organic layer (2 mL) with the lower layer from before (5 mL) and dry it using sodium sulfate. To dry, add a small scoopful of anhydrous sodium sulfate (which is a loose, granular solid) and swirl it. After a couple of minutes, make sure that at least some of the solid is still loose and granular. If so, you used enough drying reagent. If not, then you should add a little bit more. While it is drying, weigh a 25 mL pear-

shaped flask. Decant the methylene chloride solution into the tared flask and evaporate the solvent on the rotary evaporator. Weigh the flask again to determine the mass of the oil. Testing for the alkene Add 0.5 mL of methylene chloride to your oil and swirl to dissolve it. Add 2 drops of 2% bromine solution. Swirl to mix and observe whether the resulting mixture is a light red-brown color or a light yellow to colorless solution. If the solution is red-brown color, then free Br2 is present. If the color is yellow to colorless, then there is not Br2 present (and therefore the Br2 that you added must have reacted with the cinnamaldehyde. Calculations Calculate the percent recovery of cinnamaldehyde from the ground cinnamon. Discussion Suggest (with good reasons!) whether your percentage accurately represents the amount of cinnamaldehyde present in cinnamon. Briefly explain what was happening during your azeotropic/steam distillation. Identify what the composition of the distillate you collected was. Explain why an extraction was still necessary after the distillation. Explain what the bromine test told you about the cinnamon oil you isolated and how the test worked (what is the chemistry behind the test).