Synthesis of Acetylferrocene

Overview

Ferrocene is an organometallic “sandwich” compound. Two organic rings are the “bread” and a single iron atom provides the “filling”.

ferrocene

Ferrocene is intriguing for several reasons. Are there 10 iron-carbon bonds? If there are, are they all equivalent? Are the bonds ionic or covalent? Huckel’s rule says that ferrrocene’s rings are aromatic like benzene’s. Does ferrocene undergo the same kind of chemical reactions as benzene?

This experiment investigates ferrocene’s chemical reactivity by attempting a Friedel-Crafts acylation reaction, a chemical transformation typically observed in aromatic compounds. The reaction product is purified using chromatographic techniques – dry-column flash chromatography and thin layer chromatography – and is characterized by its NMR spectrum and melting temperature.

Time required: 2 laboratory sessions