Hi! Can u please answer this question for me, thanks, my professor doesn\'t expl

Question

Hi! Can u please answer this question for me, thanks, my professor doesn't explain it.

Acetyl Ferrocene (shown below) is an aromatic organometallic compound that can be prepared using the reaction scheme shown below. Often time in this reaction two products form, acetyl ferrocene and diacetyl ferrocene. If a scientist wanted to synthesize in lab acetyl ferrocene using this reaction a purification technique such as column chromatography is usually employed to purify and isolate the desired product. The column chromatography typically used has alumina as the stationary phase and the mobile phase used has a gradient. First 100% hexanes is used to evaluate the first band then the mobile phase is changed to 50/50 mixture of dichloromethane and hexanes to evaluate the two remaining bands. Assuming the reaction did not go to completion and starting material is present in addition to the two product, which fraction should the scientist keep if the desired compound is acetyl ferrocene? Explain your answer.

Explanation / Answer

The band which got eluated with 100% hexane is your ferrocene. Ferrocene dissolves completely in hexane.

The second fraction is your product (mixture of mono-acetyl and diacetyl), which you were eluting with 50/50 Hexane and chloroform.

Your product will not be soluble in hexane.

On increasing the polarity of solvent, first mono acteyl ferrocne will come and then further increasing the polarity your diacetyl product will come.

The order of getting the compounds from column are

ferrocene first, monoacetyl ferrocone second and finally diacetyl ferrocone. (if you increase your solvent polarity step wise. Increase polarity means keep on increase the chlorofom % in hexane-chlorofom mixture).

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