CH303: APPLIED CHEMISTRY

Name: Nau Sihoiata Fau (S11176348)

Lab Partner: Shweta Kumar(S11149564)
Date of the Experiment: 8/03/2021

1. PREPARATION OF FERROCENE (II-C5H5)2Fe

2. ABSTRACT
In this experiment, a preparation of ferrocene was made by reacting FeCl 2.4H2O with finely
cracked cyclopentadiene in the presence of KOH. The amount of ferrocene obtained from this
experiment was 32.11%. The crude ferrocene was then concentrated on a water bath to form
crystalline product of ferrocene. The bond between Fe – Cp bond was characterized by peak
showed at the appendix of the lab handout in which to compare the H’ n.m.r of ferrocene and
the product of the reaction with acetyl chloride.

3. PRINCIPLE
Synthesis reaction that took place in the preparation of ferrocene:
2 C5 H 6 +8 KOH + Fe Cl2 . 4 H 2 O → Fe ¿

4. REQUIREMENTS:
CHEMICAL APPARATUS

Dimethyl sulphoxide Distillation set up

KOH Two boiling tubes

Anhydrous ferrous chloride Beaker and spatula

cyclopentadiene Filter funnel and filter paper

Nitrogen gas Watch glass

vial
Bowl with ice

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5. INTRODUCTION
In this experiment, a preparation of ferrocene was made. Ferrocene is classified as a
“sandwich” compounds in which a metal is bonded to two organometallic compounds, the
discovery of this organometallic compounds was P.L. Pauson and Kealy during their experiment
to produce fulvalene, however they reacted Grignard reagent C 5H5MgBr with FeCl3 in the
company of solvent anhydrous diethyl ether the product of this was an orange solid substance
which therefore known as ferrocene [ CITATION AHa84 \l 1033 ]. In other words, ferrocene is a
subclass of sandwich compounds recounting molecules where a metal iron is bonded to two
cyclopentadiene anions. The two anions cyclopentadiene are aromatic in nature structure them
in a very stable form. The stability of ferrocene is more attributed to its electron count of 18 in
which this obeys the noble gas rule[ CITATION EAS55 \l 1033 ]. The production of ferrocene makes
it unique as it useful in many applications such as medicine and catalyst.

Purposely, this experiment is set out to prepare ferrocene and comparison its n.m.r spectrum of
the pure compound to that found for the product from the reaction of acetyl chloride.

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6. EXPERIMENTAL
This experimental was entirely held in a fume cupboard. Upon preparing ferrocene, the
cyclopentadiene was initially prepared before we conduct this lab experiment.

(Figure 1: A nitrogen gas filling in the boiling tubes and close quickly after it is added)
Two boiling tubes was used and fitted with a cork, the first tube contain 6ml of dimethyl
sulphoxide and 3 g of KOH. The second tube contain 10ml of dimethyl sulphoxide and 2g of
anhydrous ferrous chloride. The boiling tubes was then filled up with nitrogen gas
After adding the nitrogen into the boiling tubes, the next operation was done quickly to prevent
air access into the tubes. A 4ml of cyclopentadiene to the KOH suspension, stopper the tube
and shake well to mix the reaction inside.

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(Figure 2: A dark red-brown solution was transferred into 200ml beaker)

A dark red-brown colour began to develops this take 2-3 minutes to develop, this was followed
by adding a ferrous chloride solution and the mixture was shake until it all well mixed. The
mixture was then allowed to cooled for 5 minutes then it was poured into 100ml of cold water,
the result product was filter out using buchner funnel. After drying for 20 minutes, the solution
and filter paper was then transferred into 200ml beaker. A 50ml of petrol was added to the
200ml beaker then put it on the heated to boil on water path. The solution was then filtered
into 200ml beaker using a fluted filter paper with a filter funnel. The orange solid product was
then concentrated in a water path to crystallize.

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7. RESULTS

Ferrocene an air-
stable, orange solid.

(Figure 3: An orange solid product of ferrocene)

Results Obtained:
Melting Point Range of 174−179 ℃
Fe(C5H5)2
Empty vial 15.0809 g
Empty vial + product 15.7231 g
Mass product 0.6422 g

KOH CP

m(KOH )=3.090 g v(CP)=4.01 ml

Mr( KOH )=56.106 g /mol c (CP )=0.8012 g /cm3

n(KOH )=? ∴ m ( CP )=c × v=3.216 g

n(KOH )=m/Mr=0.055 mol n(CP )=3.216 g/66.1≫¿ mol

n(CP )=0.048 mol

FeCl2 (anhydrous)
m(FeCl 2+beaker )=51.908 g
m(beaker )=49.824 g
5|Page m(FeCl 2)=2.084 g
n(FeCl 2)=2.084 g /126.75 g /mol
n(FeCl 2)=0.016 mol[ Limiting reagent ]
 CH303: APPLIED CHEMISTRY

Calculations:
actual yeild 0.6422 g
% Yeild = × 100= ×100=32. 81%
theoretical yeild 2 .084

8. DISCUSSION
As the results shown, the unique characteristic of ferrocene is due to its unusual constancy for a
compound containing only a hydrocarbon and transition metal. The cyclopentadiene ligands
have a 1-charge, forming the iron on a 2+ oxidation state with a d8 electron count. Since each,
cyclopentadienyl ligand donates 5 electrons to the complete structure and Fe 2+ contributes 8,
ferrocene has a very stable electron count of 18. The synthesis of ferrocene was carried out
using cyclopentadiene and anhydrous ferrous chloride in the presence of KOH in which the KOH
used to deprotonate the cyclopentadiene. While ferrocene is quite stable in air, the
cyclopentadiene anion and Fe2+ ions used to create the ferrocene are both susceptible to
oxidation by oxygen. For this reason, it was necessary to insert nitrogen gas in the boiling tubes.
The hydrochloric acid was required to neutralize any remaining KOH. Because acid-base
neutralizations are exothermic in nature, ice was required to cool the reaction mixture as
ferrocene state at low temperatures.

The percentage yield was 32.81% of the crude ferrocene obtained, the low in percentage yield
is due to the loss of product during the experiment and possible poor conversions of reactants
to product due to the speeds at which the experiment steps is carried out. Another error that
could lead to low percentage yield is the deprotonated of cyclopentadiene was not fully
deprotonated, without this, the cyclopentadiene would not be able to react to form ferrocene.

An H’ n.m.r of ferrocene was obtained for analysis, peaks showing C-H alkene bond showing ten
equivalent aromatic protons as a singlet between 4.12-4.17ppm and the product of the reaction
with acetyl chloride showing five corresponding aromatic proton singlet o 5.62ppm for the
cyclopentadiene ring. According to [ CITATION Quy14 \l 1033 ] Fe-CP bond is characterized at 471
cm-1 showing a strong peak of Fe-CP bond.

9. QUESTION – ANSWER
a. The significant of the prefix Π is the formula of ferrocene shows the two anions
cyclopentadiene that the metal iron is bonded to or the two cyclopentadiene ligands that the
metal is bonded to, to form the organometallic compounds in other words is called the
hapticity, whereby the coordination of a ligand to the metal center.
b. Ferrocene is known as the most stable organometallic compounds; this is due to its
reversible redox properties and the two-rotatory co-planar cyclopentadiene rings surround it
hence its orange crystal packing.

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c. As shown by the H’ n.m.r spectrum of ferrocene and the product from the reaction of acetyl
chloride, the chemical shifts of ferrocene is an alkene C-H bond and it shows 10 corresponding
aromatic protons as a singlet between 4.12-4.17 ppm. Comparing this to the monoacetylated
ring, the H’ n.m.r of acetyl chloride shows 5 equivalent aromatic protons as a singlet around
5.62ppm for the cyclopentadiene ring.
d. The KOH was used to deprotonate the cyclopentadiene and make it reactive to towards the
Fe2+ ions while DMSO act as a solvent and it is used to conserved the oxidation state of the iron
as DMSO make the FeCl into a solution since it act as a polar solvent.
e. If a Lewis acid is donated to an acyl halide in the company of an aromatic ring, an
electrophilic aromatic substitution reaction can take place in which the acyl group contribute to
the aromatic ring (lead to loss of HX). As with the Friedel-Craft alkylation, the Lewis acid in the
Friedel-Crafts acylation can be differ. AlCl3 is frequently used, but FeCl3 and other Lewis’s acids
can also do the job [ CITATION Jam21 \l 1033 ].

10. CONCLUSION
In summary, the aim of this experiment was well achieved as to prepare ferrocene and
compare its n.m.r spectrum to the product of the reaction with acetyl chloride. The preparation
of ferrocene was done by reacting anhydrous ferrous chloride with cyclopentadiene in the
presence of KOH. The crude product of ferrocene was found to be 32.81% yield, the result of
this was mainly due to experimental errors such loss of product, not adding the reagent too
quickly that leads to insufficient deprotonation of cyclopentadiene. The experimental errors can
be improved by assigning more time to complete the experiment steps also to carefully read
and understand the procedure. However, to analyze the ferrocene, a H’ n.m.r spectrum was
obtained as shown by the appendix of IR spectrum of ferrocene in the handout appendix.

11. ACKNOWLEDGEMENT
I would like to acknowledge the lab explain the purpose of this experiment and to my lab
partner for showing good team work throughout this experiment, this experiment would not
have been completely if it was not for the helping hands of my partner.

12. REFERENCES

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A. Harada and S, T., 1984. Preparation and Properties of Cyclodextrin Inclusion Compounds of
Organometallic Complexes. Ferrocene Inclusion Compounds. Clathrate Compounds, Molecular Inclusion
Phenomena, and Cyclodextrins, Volume 3, pp. 791-798.

Ashenhurst, J., n.d. Master Organic Chemistry. [Online]

Available at: https://www.masterorganicchemistry.com/2018/05/17/friedel-crafts-alkylation-acylation/
[Accessed 20 3 2021].

E. A, S. a. L. S., 1955. Structure of Ferrocene. Journal of Chemical Physics , Volume 23.

Quynh Sam, S. M. a. R. W., 2014. Experiment V: Preparation and Purification of Ferrocene , s.l.: s.n.

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