Acetylation of Ferrocene and Column Chromatography

Name: Shara Myers TA's initials __________________________

1. (1 pt) Name of experiment:

Acetylation of ferrocene and column chromatography

2. (2 pts) Purpose of experiment:

To synthesize an organic compound by means of 2 chromatographic separation methods:

Gravity column chromatography and thin layer chromatography. The chemistry of the product is based on acid-catalysed aromatic substitution.

3. (5 pts) Balanced equation(s) for main reaction(s) (show catalysts):

4. (13 pts) Summary of experimental procedure:

a. (5 pts) Reaction stage:

Acetylation Reaction: In a 10 mL round bottom flask with a dry air condenser topped with a CaCl2 drying tube, water was boiled in a 250 mL beaker. The reaction started with 1mL of acetic anhydride and one drop of 85% phosphoric acid and mixed. 100 mg Ferrocine was mixed in and quickly placed with air condenser and drying tube. The flask was heated in the hot water for 3 minutes and swirled, chilled in ice, removed and neutralized to a pH of 8 using pH papers to test along with the addition of NaOH drop wise. The mixture was chilled for 15 minutes and collected via vacuum filtration and washed with ice water. It was dried as much as possible and weighed.

b. (5 pts) Work-up (isolation of crude product):

Separation of Mixture:

A Chromatography column was prepared as directed in the Lab manuel1 page 27. Toluene was added drop wise to the product and swirled till the product was dissolved. Petroleum ether was drained in the column until it was just above 1 mm to the top of the sand layer. The dissolved sample was dropped into the sand and rinsed with toluene and drained. ‘it was drained and rinsed again using a little petroleum ether. The column walls were washed with petroleum ether ad drained. The procedure as repeated until all the colored material was on the alumina below the sand and the solvent above the sand was perfectly colorless.

c. (3 pts) Final purification:

Elution: First petroleum was eluted to bring down the ferrocene. The column was filled with petroleum there and drained into the waste container. When the yellow ferrocene reached the stopcock, one of the two tarred screw capped vials were used to collect the sample until all the yellow ferrocene had drained out. Afterwards, the waste container collected clear sample as diethyl ether was poured until the orange band reached the stopcock. The 2nd tarred vial was used to catch