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Organic Chemistry (CHM2211L) Post Lab #7

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Sandra Watson
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compare the tlc plates for the crude sample and the sample that was purified

Post Lab #7 – I earned an A in this lab class.

University

University of South Florida

Introduction/Background
Discovered in 1951, ferrocene has a chemical sandwich structure in which two
anionic cyclopentadienyl rings each donate 6 Π electrons to the Fe2+ cation that resides
between them.1 The cyclopentadienyl rings in ferrocene make the compound aromatic
because each ring contains 6 delocalized Π electrons, similar to benzene, which follows
the 4n+2 rule.1 This is apparent because when ferrocene is deprotonated by a strong base,
a lone pair of electrons can combine with the 4 electrons from the two Π bonds to
establish aromaticity within each ring.1
Ferrocene is a compound that can be easily prepared and purified in the laboratory
using dicyclopentadiene, potassium hydroxide and iron chloride tetrahydrate.2 First,
dicyclopentadiene is cracked via heating into a monomer – the cyclopentadiene is
continuously distilled over.2 Then, the cyclopentadiene is deprotonized using a strong
base, like potassium hydroxide.2 Finally, iron is added to the mixture, like in the form of
iron chloride tetrahydrate, to form ferrocene.2 Due to its aromaticity, ferrocene undergoes
Friedel-Crafts acylation and alkylation.3 It can also be formylated, sulfonated or
metalated with n-butyllithium, phenylsodium and mercuric acetate.3 Ferrocene has the
ability to be arylated with diazonium salts, as well as treated with isocyanates to produce
amides.3 However, unlike typical aromatic compounds, ferrocene does not have the
ability to undergo reactions like nitration or direct halogenation because it leads to the
destruction of the molecule.3 This is most likely due to the oxidation of the iron atom.3

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Organic Chemistry (CHM2211L) Post Lab #7

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