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

2 C5H6 + 8 KOH + FeCl2.4H2 - Fe (C5H5)2 + KCl + 6 KOH.H2O

C5H6 is a limiting reagent
2.8 g 1 186.05 g
expected mass of Fe (C 5 H 5)2= =3.94 g
66.11 g /mol 2 mol
2.06
%yield= 100=52.28
3.94

compound Experimental peaks cm-1 Literature peaks cm-1

ferrocene 3923.81-2437.56 3440.70- 3094.34
2054.18-1748.52 1636.31- 1105.73
1614.43-777.98
Acetyl ferrocene 3808.28-2439.22 3562.12-2896.12
1692.23-898.93 1692.12-500

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.

Assignment
1. 2 C5H6 + 8 KOH + FeCl2.4H2 - Fe (C5H5)2 + KCl + 6 KOH.H2O

Ferrocene

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

https://pubchem.ncbi.nlm.nih.gov/image/imgsrv.fcgi?cid=15618650&t=l
.

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.