Lecture 5 Acetylferrocene 021810_1

Lecture 5 Acetylferrocene 021810_1 - Lecture#5 Synthesis of...

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Lecture #5 – Synthesis of Acetyferrocene Fe + H 3 C O CH 3 O O Ferrocene Acetic Anhydride Fe + CH 3 O H 3 C OH O Acetylferrocene Acetic Acid H 3 PO 4 heat
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Announcements!!! Make sure to turn in your samples to the correct bin; Labeled samples correctly Look for your spectra prior to the night before your report is due H 2 SO 4 not H2SO4; 2 H not 2H
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Ferrocene Part of a family of compounds called sandwich compounds Think of it as an orange between two slices of bread http://www.3dchem.com/imagesofmolecules/Ferrocene.jpg
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Ferrocene Dative interaction Fe Fe Fe 2+ Ferrocene
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Organometallic Complex Organic component Metal component More an interaction than a single bond Ferrocene can be a Catalyst C-C, C-N forming bonds Asymmetric synthesis chiral molecules with chiral organometallic catalyst
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How is it made? It comes from cyclopentadiene dimer Obtained through a process called cracking Dimer is broken apart with heat Fe is inserted Fe starts out in +2 oxidation state (FeCl 2 . 4H 2 O) In ferrocene it is in the +2 oxidation state The overall charge on the molecule is 0 How can that be???
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Cyclopentadiene If the Fe has a +2 charge and the molecule has an overall net 0 charge then somewhere in the molecule we need to balance the charge Comes from the cyclopentadienyl ring It is an anion Each ring has an overall -1 charge The circle inside the pentagon represents aromaticity (like benzene)
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This note was uploaded on 06/28/2010 for the course CHEM 258 taught by Professor Taylor during the Spring '10 term at Wesleyan.

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Lecture 5 Acetylferrocene 021810_1 - Lecture#5 Synthesis of...

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