Experiment 7A The Synthesis of Artificial Hyacinth Odor (1-bromo-2-phenylethene), Part I

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1 Experiment 7A The Synthesis of Artificial yacinth Odor (1-bromo-2-phenylethene), Part I This two-step synthesis involves the following conversion: trans-cinnamic acid 2,3- dibromocinnamic acid 1-bromo-2-phenylethene (equation 1). The addition to double bonds and the elimination of alkyl halides to form double bonds are the two major reactions involving alkenes. The first is a reaction of alkenes and the second a method of synthesizing them. In this experiment we will perform the first of the two steps that lead to the synthesis of 1-bromo-2-phenylethene. This material is used in the manufacture of hand soaps since it has a pleasant hyacinth like odor. Each step is discussed in more detail in each individual part of the lab along with experimental procedures. Overall Reaction Sequence: O trans-cinnamic acid (3-phenylpropenoic acid) O C 3 CO 2 2,3-dibromocinnamic acid (2,3-dibromo-3-phenylpropionic acid) K 2 CO 3, heat (1) CO 2 1-bromo-2-phenylethene (artificial hyacinth odor)

2 Experiment 6A: Preparation of 2,3-dibromocinnamic acid from trans-cinnamic acid. INTRODUCTION The sequence is started by the addition of bromine to a double bond. This reaction, classically carried out with liquid bromine, occurs in this experiment by the use of. Liquid bromine is a very dangerous chemical. It is volatile, extremely corrosive and very toxic. N - 2 On the other hand, is a solid that can be weighed out; it is less volatile and so is easier to handle. It is, however, just as toxic and corrosive as bromine so even though easier to handle it must be treated with great respect. The bromine is added across the double bond of 3-phenylpropenoic acid (trans-cinnamic acid). The reaction is carried out in glacial (100%) acetic acid (equation 2). O trans-cinnamic acid (3-phenylpropenoic acid) O C 3 CO 2 2,3-dibromocinnamic acid (2,3-dibromo-3-phenylpropionic acid) (2) The reaction likely involves the intermediacy of a bromonium ion, a cyclic cation consisting of a (partially) positive charged bromine atom bonded to two carbons of the incipient double bond. The protonated carboxyl group (remember the acid solvent) ensures that there is substantial partial positive charge on the carbon substituted, and resonance stabilized, by the phenyl group. This assertion is supported by the following observation: the reaction carried out in the presence of high concentration of a competitive nucleophile, chloride anion, yields 2-bromo-3-chloro-3-phenylpropionic acid but none of the 3-bromo-2-chloro-3-phenylpropionic acid. While this has no consequence for this particular transformation of this experiment, it is critically important when this addition reaction is used to obtain high regioselectivity and

3 stereoselectivity. The reaction is run using glacial acetic acid as the solvent. Not only is the acetic acid used as the catalyst for this reaction, it also allows the product to be obtained via crystallization. It would be possible to use another solvent and an added acid to provide the catalyst needed for this reaction but using the acetic acid allows the product to precipitate. Acetic acid is soluble in water and the product is not. A simple addition of water allows us to isolate the product from the reaction mixture. This experiment involves mixing the reactants and trans-cinnamic acid together in a round-bottom flask to which is attached a watercooled condenser. The flask is heated with a heating mantle until the reactants boil. This technique is called heating under reflux. The temperature at which the reactants boil is never specified nor determined because the boiling temperature depends on the chemicals being heated. To get to reflux temperature, the flask is simply heated until vapors are observed in the condenser, at which time they recondense into the reaction flask. With this technique, none of the reactants or product(s) can escape. They are kept heated and in contact with each other at all times until the reaction is complete. The length of heating must be determined experimentally for each reaction. An insufficient heating time gives a poor yield of product(s) and there is usually a heating time beyond which no more product is formed. In this experiment, the reaction is heated at reflux for about 30 minutes, which has been found to give a reasonable yield of product. The time a reaction needs to reflux depends on the temperature of the boiling solvent and the nature of the reaction. The addition of bromine to a double bond is very fast and the boiling point of the acetic acid is fairly high so one doesn t need a long reflux. The solution is transferred to an Erlenmeyer flask because we are about to induce crystallization of the product and it is easier to do this in a flat-bottomed Erlenmeyer flask than a round-bottom flask. Two milliliters of acetic acid are used to rinse the reaction flask and ensure all material (or as much as possible) is transferred to the Erlenmeyer flask. Addition of the water reduces the solubility of the product to the point that the product precipitates. More water will produce more precipitate, but risks the precipitation of impurities and generates a larger volume to manipulate. A compromise between purity, convenience and yield must be made. Ideally, crystallizations are carried out slowly. A slow crystallization allows the formation of crystals with the best purity. Thus, water is added drop-wise with stirring to allow slow crystallization. The product is vacuum-filtered and freed from the bulk reaction solvent with its by-products and impurities, but still retains undesired material on the surface of the crystals. The undesired material is removed by rinsing the crystals. If you recall, there was a slight excess of. This material is destroyed by bisulfite ion. The inorganic byproducts, and the acetic acid are washed off the product by water. Cold water is used to minimize loss of the product. The number of washes is a compromise. If the product smells of acetic acid, then more washes will remove the

4 excess acetic acid; but, more washes will dissolve some of the product. Another compromise must be made. Two or three washes appear to yield good quality product. REAGENT/PRODUCT TABLE: Reagents MW (g/mol) MP (ºC) BP (ºC) Density (g/ml) pyridinium bromide perbromide cinnamic acid glacial acetic acid Products MW (g/mol) MP (ºC) BP (ºC) Density (g/ml) 2,3-dibromocinnamic acid EXPERIMENTAL PROCEDURE FOR YOUR SAFETY 1. Pyridinium bromide perbromide is a lachrymator (fumes may cause the eyes to fill with tears) and is corrosive contact with it may lead to severe burns. 2. Wear gloves at all times when handling. 3. Avoid inhaling. 1. To a 50 ml round bottom flask equipped with a magnetic stir bar add 2.2 grams of trans-cinnamic acid (3-phenylpropenoic acid). 2. To the same flask add 5.3 grams of (cautioncorrosive). 3. To the reaction flask add 17.5 ml glacial acetic acid (corrosive). 4. Place your hotplate on the bench top, set the heating mantle in the center of the hotplate (make sure the hot plate is off!). Position your round-bottom flask in the heating mantle and firmly clamp in place at the neck of the round-bottom flask. Attach a reflux condenser to the 50 ml flask (second clamp at the top of the condenser) and turn on water, making sure that the water is flowing in the bottom and out the top. A mini-hood should be positioned above the opening of your condenser to prevent you from smelling any fumes. 5. Start the stirrer at a setting of 5 or 6 (stirring prevents bumping!) and set the temperature control to 119 on the Variac. 6. Allow the mixture to reflux for 30 minutes after starting to boil. 7. After 30 minutes of refluxing, cool the mixture to room temperature in a cool water bath (beaker). 8. Carefully transfer the solution to a 50 ml Erlenmeyer flask. Complete the transfer by rinsing out the reaction flask with an additional 2 ml of glacial acetic acid and adding it to the Erlenmeyer flask. You will need the stir bar to be transferred as well.

5 9. Place the Erlenmeyer flask on your stir-plate (use a clamp to prevent it from falling over). While stirring, allow it to continue to cool for 5 minutes. 10. To the rapidly stirred (stirrer set at 6-7) reaction mixture, slowly (over a total of 5-10 minutes) add 15 ml of cool water. Then place the Erlenmeyer flask in an ice bath to complete the crystallization. 11. Further cool the Erlenmeyer flask in an ice bath for at least 5 minutes. 12. Filter the product from the crystallization solution by using a Büchner funnel. 13. When the solid product has drained, rinse it with a 5 ml portion of 10% sodium bisulfite, followed by two washes with 5 ml portions of ice-cold water. Pour the rinse solution onto the crystals quickly so that the entire product is washed. The product, originally pale yellow should become white. 14. Leave the product in the top of the Büchner funnel which should be placed on the floor of your drawer to dry until next lab period, at which point you will obtain the final weight and melting point of your dried product. Submit product upon completion of the lab. CALCULATIONS 1. Calculate the moles of used. 2. Calculate the moles of trans-cinnamic acid used. 3. Determine which component is the limiting reagent. 4. Calculate the theoretical yield of 2,3-dibromocinnamic acid (in grams) 5. Calculate the percent yield of 2,3-dibromocinnamic acid. WASTE DISPOSAL Place the filtrate contained in the filter flask in the aqueous acid waste bottle. All filter paper waste can be placed in the trashcan.

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