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Isolation of Limonene
Objectives: To isolate a naturally occurring hydrocarbon, called limonene, and to perform a test to show that it is unsaturated. Introduction Limonene occurs naturally in orange and lemon peels and in dill and caraway seeds. It has a number of commercial applications. For example, it is used as orange flavoring in some types of candy, and it is added to dog shampoo to kill fleas. Its purpose in certain plants may be to provide protection by acting as a natural insecticide. Limonene is a hydrocarbon and is therefore not soluble in water. Its boiling point (175 o C) is much higher than that of water. However, for reasons which will not be explained here, it will vaporize rapidly in the presence of boiling water. This is true of many other organic compounds as well, and it provides a means of isolating certain compounds from a mixture such as an orange peel. This method is called steam distillation and it is very useful variation of ordinary distillation. A molecule that has one or more carbon-carbon double (or triple) bonds is said to be unsaturated. After you have obtained some limonene in this experiment, you will do a simple test to show that limonene is unsaturated. This test consists of allowing the limonene to react with bromine (Br2). Although Br2 is red, it reacts with unsaturated compounds to give a less colored or colorless product. by allowing the limonene to react with Br2 and observing the red color of Br2 changing, you are showing that limonene is unsaturated.

carbon-carbon double bond limonene Procedure: Peel one large orange, or two small oranges. Weight the peels and place them in a blender along with 400 mL of deionized water. Blend the mixture for 30 secs until it has the consistency of a thin milk shake. Carefully pour this mixture into a 1 L Florence flask using a funnel. Set up a steam distillation apparatus (see drawing) as follows: 1) put the hot plate on the lab bench and set the flask on the hot plate. 2) attach the still head. 3) attach a condenser to a ring stand or support with a three fingered clamp. 4) place a hose from a water tap in to the lower part of the condenser (water inlet) and place a hose from the water outlet to the drain. 5) turn on the water and make sure there are no leaks and water is running through the condenser and down the drain.

2 Have your instructor inspect your apparatus before you begin. When this has been down, turn on the hot plate to high, but adjust it lower if the mixture boils too vigorously. Collect about 75 ml of distillate (a liquid) in a separatory funnel. The funnel is held in a small ring clamped to a ring stand or support. When finished, turn of the heat on the hot plate. Disassemble the apparatus. Remember, it is hot. Dispose of the orange pulp by pouring it in an ice bucket. Do this while it is hot, otherwise it tends to stick to the inside of the flask and make cleaning difficult. At this point, your separatory funnel should contain a small (and difficult to see) layer of limonene on top of a large amount of water. Carefully drain the water from the separatory funnel leaving only the limonene. The limonene layer will be come more noticeable as the water drains out. Using a long Pasteur pipet, and being careful to avoid any droplets of water, remove the limonene from the separatory funnel and transfer it to a pre-weighed 4 dram vial. Weigh the vial with the added limonene. Find the weight of limonene and determine the % yield. The water from the separatory funnel can be poured down the drain. Place 1-2 drops of 1% Br2 in CH2Cl2 into a small clean test tube. Caution: Br2 is corrosive; avoid contact and breathing vapors. Add a drop of your limonene and observe the results. Look for any discoloration of the bromine solution. Dispose of the material in the test tube by pouring it into the chlorinated organic waste bottle.

Report Sheet
Describe the limonene that you isolated (color, odor, physical state, etc.)

mass of orange peels mass of limonene

______________ ______________

Based on the above data, what percentage of an orange peel is limonene? Show your work.

Describe what happened when a drop of limonene was added to the Br2 solution.

Based on your observations above, what can you conclude about limonene?

4 Explain how distillation works.

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