The Diacetylferrocene Melting Point

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The melting point of ferrocene is 173 C. The simplest form of the metallocene, ferrocene is an organometallic compound with two parallel five-membered carbon rings and an iron ion sandwiched between them. The bonds between the rings are pi orbitals, whereas the bonding to the ions is usually of d-orbital nature.

A common synthesis lab experiment in undergraduate chemistry classes is to synthesize a chemical from a single reaction. The goal is to understand the mechanism of this synthesis.

In this laboratory, you will be attempting to synthesize the diacetyl form of ferrocene. The synthesis is a simple reaction of aluminum chloride and acetyl chloride in water. The reagents are dispensed in snap cap vials instead of beakers to prevent the reaction from overheating or boiling, giving unwanted side reactions.

During the synthesis, you noticed that the water removed the ionic salts like NaCl and aluminum chloride/hydroxide, but it also removed the polar organics like acetyl chloride. Why was this?

Adding more acetone to the solvent increased its polarity. This meant that it was better able to pull all of the compounds up the silica gel TLC plate and separate them. The order of elution from the column was ferrocene>acetylferrocene>diacetylferrocene. The order was determined based on the interactions at the molecular level, not just the physical properties of the material.

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