These questions are from an experiment where we had a mixture of Ferrocene, acetylferrocene and diacetyl ferrocene and we separated each by using column chromatography. Before doing the column chromatography we did TLC analysis to ensure that we did, in fact, have a mixture of these 3 compounds. During the column chromatography we first eluted the ferrocene using pure hexane. Then we eluted the acetylferrocene using a 1:1 mixture of hexane and methylene chloride. Then we eluted the diacetylferrocene using a 9:1 mixture of hexane and methylene chloride.

1. Rank ferrocene, acetylferrocene, and diacetylferrocene in order of increasing polarity. Do the TLC results from your fractions support this ranking? Explain.

2. Rank the solvents used in the experiment in order of increasing polarity.

3. Why do you start with the least polar solvent/solvent mixture and progress to increasing polar solvent/solvent mixtures when eluting the ferrocene compounds from the column rather than starting with more polar solvent system and progressing to less polar solvents?

4. How do the thin layer and column chromatography for this experiment compare in regard to stationary and mobile phases?

5. What key feature in the IR spectrum of acetylferrocene distinguishes it from the spectrum of ferrocene?

Explanation:

The polarity of the 3 compounds would be in the order of

Ferrocene < Acetylferrocene < Diacetylferrocene

Your TLC data has to also support this observation . This can be checked by measuring the values of Rf ( Retention factor = distance travelled by solute/solvent ) .The Rf values also has to follow this particular order: -

Ferrocene > acetylferrocene > diacetylferrocene

2) Hexane happens to be a non-polar solvent. The polarity of hexane can be increased if some polar solvents for example, ethyl and methylene chloride etc are added

Therefore, in the increasing order of solvents polarity, we have

Hexane < 1:1 mixture of hexane: methylene chloride < 9:1 mixture of methylene chloride:

3) Chromatographic techniques all have a stationary phase in addition to a mobile phase. In the case of column chromatography, the silica gel will be the stationary phase and the solvent that will be poured will be the mobile phase.

4) The TLC and column chromatography both happen to have the same stationary phase which is the silica gel. Also, the same solvent mixture is used in both the techniques. This makes the result of the 2 to be almost the same. The difference seen between them is that, TLC works against the gravity while on the other hand column chromatography works in the direction of the gravity.

5) The key feature in the IR spectra of the acetylferrocene that will be absent in the spectra of ferrocene is the presence of carbonyl stretching frequency at close to 1700 per cm(cm-1). This peak is easily differentiated between both acetyl ferrocene and ferrocene.