2 Acylation of Ferrocene Ferrocene, an iron-based orange crystalline solid, has

Question

2 Acylation of Ferrocene Ferrocene, an iron-based orange crystalline solid, has properties of a typical aromatic compound. It is an unusually stable, soluble in common organic solvent, and does not react readily with acids and bases. However it is sensitive toward oxidizing agents. This compound has found many applications in materials science, including catalysts. Also, it is use as a fuel additive. The errocene derivatives are highly active against several diseases, including some type of cancer Depending upon the catalyst and the reaction condition, the major acetylation product is either monosubstituted product or the disubstituted product. In this lab you will probably isolate a mixture of ferrocene, acetylferrocene, and diacetylferrocene. Ferrocene can also be converted to many other useful derivatives. Do you expect ferrocene or benzene be more reactive in electrophilic aromatic substitution? What does the Friedel-Crafts acylation of ferrocene produce, mainly acetylferrocene, diacylferrocene, or a mixture of products? Explain why that compound is the most likely by-product of this synthesis. Why does the acetylferrocene not move much on the column while the column is being eluted with hexanes? Question: Is excess of acetic anhydride necessary to effect complete acylation of the ferrocene that produces diacetylferrocene? Purpose: 1. To study the Friedel-Crafts acylation reaction To illustrate the use of column chromatography for the purification of mixture 3. To evaluate the composition of your product with thin-layer chromatography (TLC) 1 Page

Explanation / Answer

Ferrocene is compound in which the iron atom is sandwiched between two cylcopentadienyl aromatic rings. The two cyclopentadienyl rings coordinate to the central iron atom. Acylation of ferrocene is done with phosphoric acid and acetyl chloride or AlCl3 and acetic anhydride.The milder catalyst phosphoric acid under mild conditions gives monosubstituted product while AlCl3 gives disubstituted product. The excess use of acetic anhydride does not effect the product it act as solvent in the reaction, the use of catalyst controls the reaction .

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