This document describes the synthesis and characterization of ferrocene and acetyl ferrocene. Ferrocene was synthesized by treating iron(III) chloride with potassium cyclopentadienyl, yielding 52.28% ferrocene. Acetyl ferrocene was produced by acetylating ferrocene, and the two compounds were separated using column chromatography. Both compounds were characterized using melting point, UV-Vis, IR spectroscopy and found to match literature values. The document also discusses electrophilic and nucleophilic reactions of ferrocene.
This document describes the synthesis and characterization of ferrocene and acetyl ferrocene. Ferrocene was synthesized by treating iron(III) chloride with potassium cyclopentadienyl, yielding 52.28% ferrocene. Acetyl ferrocene was produced by acetylating ferrocene, and the two compounds were separated using column chromatography. Both compounds were characterized using melting point, UV-Vis, IR spectroscopy and found to match literature values. The document also discusses electrophilic and nucleophilic reactions of ferrocene.
This document describes the synthesis and characterization of ferrocene and acetyl ferrocene. Ferrocene was synthesized by treating iron(III) chloride with potassium cyclopentadienyl, yielding 52.28% ferrocene. Acetyl ferrocene was produced by acetylating ferrocene, and the two compounds were separated using column chromatography. Both compounds were characterized using melting point, UV-Vis, IR spectroscopy and found to match literature values. The document also discusses electrophilic and nucleophilic reactions of ferrocene.
This document describes the synthesis and characterization of ferrocene and acetyl ferrocene. Ferrocene was synthesized by treating iron(III) chloride with potassium cyclopentadienyl, yielding 52.28% ferrocene. Acetyl ferrocene was produced by acetylating ferrocene, and the two compounds were separated using column chromatography. Both compounds were characterized using melting point, UV-Vis, IR spectroscopy and found to match literature values. The document also discusses electrophilic and nucleophilic reactions of ferrocene.
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Residences
Gumede Thulile 14305624
CMY report 2a and 2b
Synthesis, characterisation and reactivity of Ferrocene. Introduction: In this experiment, Ferrocene and Acetyl ferrocene were synthesised. A sample of crude Ferrocene supplied had a mixture of Ferrocene and Acetyl Ferrocene and was purified and separated by column chromatography were 0.13g and 0.11g of Ferrocene and Acetyl Ferrocene were yielded respectively. Both products were characterised according to UV-Vis spectrum, IR and the, melting point.
Method compound method Ferrocene Iron (III) chloride is treated with Potassium cyclopentadienyl. The reaction occurs in a three necked flask which is constantly purged with Argon for three conservative times. The mixture is then filtered and washed with 4 portions of water. Ferrocene and Acetyl ferrocene Ferrocene was acetylated and the mixture was filtered then separated by column chromatography using petroleum ether as an eluent for Ferrocene and diethyl ether as an eluent for Acetyl Ferrocene.
Results compound Melting colour mass %yield point Ferrocene 171 C- Dark 2.06g 52.28% 172.5C orange Ferrocene 173 C orange 0.13g 8.66% -181 C Acetylferroce 81.5 C Dark red 0.11g 5.98% ne -83 C
Discussion Ferrocene was successfully synthesized with a medium percentage yield. Purification of actylcyclopentadienyl (Cyclopentadienyl)iron(III) yielded very low products of ferrocene and acetylferrocene. Some of the products may have been lost during the filtering step by being washed away or not properly removed in the round flask.in the second practical separation of ferrocene and acetylferrocene was achieved through column chromatography. Petroleum ether is a hexane eluent and thus only non-polar compounds will move with this type of eluent and in this case it was acetylferrocene. The second eluent which is diethyl ether is non polar thus ferrocene is less polar and will have higher affinity for this type of mobile face.
Fe0 = 8e- 2 x C5H5 = 5e- x 2 = 10e- Total = 18e- Ferrocene obeys the 18-electron rule Nickelocene: Ni0 = 10e- 2 x C5H5 = 5e- x 2 = 10e- Total = 20e- Nickelocene does not obey the 18-electron rule. 2. The IR spectrum of ferrocene has many peaks. According to the literature, values there are not supposed to be peaks absorbed at a wavelength between 2054.18cm-1-1748.52cm-1. The reason for these peaks may be due to some of eluent, which was supposed to be discarded as first waste was added together with ferrocene. When wavelength of peaks decrease the functional groups becomes simpler. 3. Ferrocene is less polar and thus its mobile phase will be petroleum ether (Hexane). Addition of petroleum ether as an eluent will result into movement of ferrocene. Acetyl ferrocene is polar and thus will move in a mobile phase with an eluent which is polar and that eluent is diethyl ether. The aluminium foil was important in order to protect our product from light and keeping temperature of reaction constant. 4. Biscyclopentadiene
Amine method, reaction of ferrous chloride and sodium cyclopentadienide in an amine
solvent.
Grignard method, react 2(C5H5)-MgBr with FeCl2.
5. Electrophilic reactions of ferrocene are substitution based. An electron
deficient compound is attracted by an electron rich region of another compound. A rich region in ferrocene is a double bonded C-C, which then can attract electrophilic compound such as acetic anhydride. Nucleophilic reactions involves electron rich compounds, which can donate their electron pairs to electron deficient compounds. Ferrocene can act as an electrophile when one Cp bond is removed and the compound is left positively charged, a nucleophile such as t-Butyl lithium attacks the electrophile. This reaction is called lithiation. 6. 6 Fe (C5H5)2 + 3 AcCl + AlCl3 ------ Fe(C5H5)(C5H4COCH3) + Fe(C5H4COCH3)2 The AlCl3 is a lone-pair acceptor, lewis acid. Acetylchloride donates a lonepair to AlCl3 and forms an acylium ion, CH3C(O)+, which is a strong electrophillic. 7. E.O Fischer and G. Wilkinson. They both received a noble peace prize in chemistry in 1973 for their outstanding work done independently on chemistry of organometallics called sandwich compounds. This compounds feature a metal bound by haptic covalent bonds to two arene ligands. References. B.V. Lokshin, V.T. Aleksanian and E.B. Rusach. On The Vibrational Assignments of Ferrocene, Ruthenocene And Osmocene. Journal of Organometallic Chemistry, 86 (1975) 253 256. J. N. Willis, JR., M. T. Ryan, F. L. Hedberg and H. Rosenberg. An infrared and Raman study of l,ldisubstituted ferrocene compounds. Spectrochimica Acta,Vol. 24A, pp. 1561 to 1572. Pergamon Press 1968
Pamela S. Tanner, Gennady Dantsin, Stephen M. Gross, Alistair J. Lees, Clifford E.
Myers, M. Stanley Whittingham and Wayne E. Jones, Jr. [1]. The Synthesis and Characterization of Ferrocene. A Modern Iterative Approach to a Classical Organometallic Laboratory Experiment. State University of New York at Binghamton, Binghamton, New York.
