The Friedel-Crafts Reaction: Acetylation of Ferrocene

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1 The Friedel-Crafts Reaction: Acetylation of Ferrocene Objective This reaction illustrates electrophilic aromatic substitution reaction, in which an electrophile replaces a hydrogen atom in an aromatic compound forming a new carbon-carbon bond. Introduction As has been noted in earlier experiments, a unifying theme of synthetic organic chemistry is the construction of carbon-carbon bonds. Such bond-forming reactions allow the elaboration of more complicated organic structures from simpler precursors. Electrophilic aromatic substitution reactions, in which an electrophile replaces a hydrogen atom in an aromatic compound can form a new carbon-carbon bond if done with an electrophilic carbon species. Such reactions, discovered in 1877 by Charles Friedel and James Crafts and now collectively known as Friedel-Crafts reactions, may be used to introduce both alkyl ("Friedel-Crafts alkylation") and acyl groups ("Friedel-Crafts acylation"). As the following mechanism indicates, Friedel-Crafts acylation is affected by the formation of an acylium ion as the active electrophilic species. The reactive acylium ion is generated from an acyl halide or anhydride by treatment with a Lewis acid; aluminum chloride is commonly used for this purpose. Although AlCl 3 could potentially affect the catalysis of the Friedel- Crafts acylation reaction, the product, a ketone, is sufficiently basic to interact strongly with AlCl 3, so that in fact more than one equivalent of AlCl 3 is required. The AlCl 3 is removed in an aqueous workup step, which hydrolyzes it to HCl and aluminum hydroxide. 1

2 The Friedel-Crafts acylation reaction Although many aromatic compounds are based on the prototypical benzene ring system, many other aromatic compounds are known. In general, aromaticity results from a cyclic, planar, fully-conjugated array of atoms with a total of 4n+2 (n = integer) pi electrons in the delocalized pi system. Thus, neutral compounds such as pyrrole and furan, as well as charged species such as tropylium, cyclopentadienyl and cyclopropenium, all represent aromatic compounds. Typical nonbenzenoid aromatic compounds In this experiment, rather than using a simple benzene derivative as a reactant, you will explore the Friedel-Crafts acylation of a cyclopentadienyl ring contained in an organometallic compound (i.e., a compound containing one or more bonds between carbon and a transition metal). The substrate, ferrocene, contains two cyclopentadienyl rings which form a "sandwich" with the central iron atom. Although the presence of the metal atom confers some unusual properties on ferrocene, the cyclopentadienyl rings undergo many reactions typical of aromatic compounds. In particular, ferrocene efficiently undergoes Friedel-Crafts acylation, and it is this reaction that you will investigate. Friedel-Crafts acylation of ferrocene Friedel-Crafts acylation represents a powerful and effective way to introduce new carboncarbon bonds in aromatic compounds, and it has been extensively exploited as a synthetic tool since its discovery. However, the reaction is not without limitations. A strong Lewis acid, often aluminum chloride, which is corrosive and gives off HCl upon contact with moist air, is required in greater than stoichiometric amounts, leading to the generation of considerable quantities of acidic and aluminum containing waste. Common solvents for Friedel-Crafts 2

3 acylation reactions include halogenated methanes (e.g., dichloromethane) or carbon disulfide, representing environmental and/or human health risks. In this experiment, you will use a more benign catalyst, phosphoric acid, to effect the Friedel-Crafts acylation reaction. No organic solvents are used, although one of the reactants, acetic anhydride, is used in excess and thus may play the role of a solvent in this reaction. Unfortunately, these acylation conditions are not general - it is the relatively high reactivity of ferrocene, compared to simpler aromatic substrates, which allows the replacement of AlCl 3 with phosphoric acid. Discovery of new Friedel-Crafts-like reaction chemistry, applicable to simple benzene derivatives, remains an area of ongoing investigation. Experimental Procedure Safety Precautions: Phosphoric acid and acetic anhydride are corrosive, and acetic anhydride is also a lachrymator; avoid contact or undue exposure to vapor. Reaction: 1. Place 0.5xxx g. of ferrocene in a 25 ml round-bottom flask containing a magnetic stir bar. Prepare a hot water bath, heating the water to nearly the boiling point while preparing the following reaction mixture. 2. In a fume hood, add 2.0 ml of acetic anhydride and 0.3 ml (approx 15 drops) of 85% phosphoric acid to the flask. The reaction mixture should heat up and darken in color. Swirl the flask, heating occasionally in a hot water bath, if necessary, until all the ferrocene dissolves. 3

4 3. Attach a reflux condenser, then heat the reaction mixture, with stirring, in the hot water bath prepared in step 1. Heat the mixture for 10 minutes, during which time a purple color may develop. Workup and purification: 4. Pour the reaction mixture onto 25 g. of ice in a 400 ml beaker, rinsing the flask with two 5 ml portions of ice water. (A black residue may remain in the flask.) Stir the orange-brown mixture with a glass rod for a few minutes. Any insoluble black material present will be removed in the following steps. 5. Add 12.0 ml. of 3 M aqueous NaOH solution, then carefully add solid sodium bicarbonate in small portions until the remaining acid has been neutralized (about 2-3 grams). Use great care to avoid excessive foaming during this bicarbonate addition by adding the bicarb slowly. This step can be done with magnetic stirring, but make sure to use a stirring plate that is not hot. Stir well and crush any lumps, affording a dark-brown suspension. 6. Allow the mixture to stand for 20 minutes, then collect the crude product by vacuum filtration and continue to pull air through the product for a few minutes to dry it. Finish the drying process by pressing the solid product between two sheets of filter paper or paper towels. Save a bit of this crude product for TLC analysis. 7. Transfer the solid and a stir bar to a 50 ml beaker and add 10 ml of hexanes. Boil for 5 minutes with stirring, then decant the dark-orange solution into another Erlenmeyer flask, leaving behind a black gummy substance. 8. To the hot solution, add a spatula-full of decolorizing carbon (Use of too much carbon will reduce your yield). Heat with swirling, then perform a hot filtration to remove the decolorizing carbon. 9. Set the flask aside to cool slowly. Red-brown needles of acetylferrocene should begin to form. Once the flask has reached room temperature, cool it in ice. Collect the crystalline product by vacuum filtration, washing with a small quantity of cold hexanes, and dry it by continuing to pull air through it for a few minutes. 4

5 Characterization: 10. Record the yield and melting point range of your recrystallized acetylferrocene. 11. Analyze your crude and recrystallized products by TLC. Separately dissolve very small amounts of pure ferrocene, the crude product and the recrystallized acetylferrocene in a few drops of toluene. Spot the solutions on silica gel plates and develop with 30:1 toluene/absolute ethanol. Visualization is simple-each of the compounds is brightly colored. Thin layer chromatography is performed on a glass or plastic plate which is coated with a thin layer (thus the name) of solid absorbent, such as silica (SiO 2 ). The surface of the silica particles has a large number of Si OH groups, which makes this substance very polar, in other words, it is very sticky to other polar molecules. The sample mixture is spotted on the plastic plate near the bottom using a glass capillary tube, and the plate is put in a closed beaker or jar with a small amount of the appropriate solvent or solvent mixture. Capillary action draws the solvent up the plate. When the solvent front is near the top, the plate is removed from the beaker and a separation of the sample's components may be observed. If the compounds are colored (as is the mixture you will use), the plate can be read easily. If the compounds are not colored then they can be visualized by an ultraviolet lamp or a chemical stain. Some techniques for visualizing spots are outlined below: Ultraviolet light. Commercial TLC plates have a phosphor in the solid phase which fluoresces in long-wave UV light. If a compound is present on the plate it blocks this fluorescence and appears as a dark spot. A few organic compounds fluoresce themselves, and will show up as bright spots under short-wave UV light. 5

6 For each spot on the TLC plate a characteristic value called the ratio to the front, or R f, can be calculated. R f is defined as the ratio of the distance traveled by a spot (measured from the center of the spot) to the distance traveled by the solvent. Although the R f is characteristic for a given compound, it depends greatly on the solvent and the type of absorbent used. Consequently there are no tables of R f values in the CRC Handbook or Merck Index. The difference in R f values between two spots on a plate, ΔR f, which also varies with the solvent, is used as a measure of the performance of the separation. If there is no difference in R f values, there can be no separation of the components of a mixture and no way to differentiate one spot from another. The choice of solvent system is crucial for good separation. With too polar a developing solvent, all of the spots will run to the top of the plate, and ΔR f will be zero. With a very nonpolar solvent, none of the spots will move from their initial positions, and again ΔR f = 0. The best separation is often achieved by using a mixture of a non-polar with a polar solvent. The polarity of the developing solvent is adjusted by changing the ratio of polar to non-polar solvents in the mixture. The appropriate developing solvent should give an Rf of 0.3 to 0.5 for the desired compound (or the middle R f of a mixture) and a ΔR f of at least 0.1 between the desired compound and any impurities. 6

7 Pre-Lab Please set up a table of reagents and draw a reaction scheme for today s reaction. 1. Why do you think the ferrocene compound can undergo this reaction without the assistance of a strong Lewis Acid? 2. Please draw out the MO diagrams for 3 of the 5 typical nonbenzenoid aromatic compounds shown above. 3. Please predict the products of the following reactions: O 2 N O AlCl 3 Cl O O AlCl 3 Cl Post-Lab questions-will be handed out in lab. 7

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