April 15, 2024

Which diacetylferrocene product forms when ferrocene is reacted with acetic anhydride?

Which diacetylferrocene product forms when ferrocene is reacted with acetic anhydride?

Ferrocene is a diolefinic hydrocarbon which can be reacted with acetic anhydride to form diacetylferrocene. 

This product is very reactive and has found use as a catalyst in the production of polyethylene, polypropylene and acrylonitrile.

So far there has been no reported synthesis of diacetylferrocene. 

Two possible pathways for its formation are ferrocene reacting with acetic anhydride to form a carboxylated ferrocene and then reacting with another molecule of acetic anhydride to form the final product or the direct reaction between ferrocene and acetic anhydride to form diacetylferrocene.

Which diacetylferrocene product forms when ferrocene is reacted with acetic anhydride?

Many types of ferrocene compounds are colorless liquids in which single isomers exist in different concentrations. 

The most common type:-

  • Ferrocenyl
  • Acetyl acetate 

Exists in two different isomeric forms, conjoined or separated.

Here is the answer for, how to interpret your experimental data to determine which diacetylferrocene isomer forms?

Ferrocene is a hydrocarbon molecule that was first discovered in 1951 by Felix Hoffmann and co-workers. The molecule was named after its ferromagnetic properties, which means it has good magnetic properties. It was the first fully aromatic hydrocarbon produced from coal tar.

Here are some points:-

1. Ferrocene is a transition metal with the chemical formula CFe. 

Its atomic number is 25, and its valence is 3. 

It has a trigonal planar structure, and a four-coordinate Fe center. 

2. Acetic anhydride is an organic compound with the formula CHC(O)O. 

Its empirical formula is CHCOCH. 

It has a linear structure, and a C3v point group. 

The C-C bond length is 148.54 pm, and the molecule’s radius of gyration is 143.4 pm.

3. The diacetylferrocene product consists of the separated isomer.

The molecular formula for 1-diacetylferrocene is CH(CFe)CHCHCOO. 

Its radius of gyration is 275 pm, and its VSEPR formula is O3. 

This molecule has a bent shape, and it has a dipole moment of 0.24 D, with the negative charge at the C1 carbon atom. 

The bond angle at C1 carbons atoms is 165°, and the bond angle at the C2 carbons atom is 109°. 

It has an electron density of 0.

4. In the separated molecules, the two ferrocene chemical bonds are staggered 

It has a total bond order of 3.5, and a dipole moment of 2.15 D. 

The zigzag structure is oriented with its longer axis along the y-axis and its shorter axis along the x-axis, and it has an m value of 1 and an e value of 0.4 (e/2 = 0).

5. The molecule, with its two separate isomers.

It has the molecular formula CH(CFe)CHCHCOO. 

The molecule has a bent shape, and it has an alpha-tautomeric form with one chiral center.

The C-C bond length is 270.60 pm, the C-O bond length is 126 pm, and the C-F bond length is 114.46 pm. 

The bond angles at the C1 carbon atoms are 204° and 131°, while the bond angles at the C2 carbon atoms are 105° and 111° respectively.

6. Calculate the molecular formula for 1-diacetylferrocene. 

The sum of the subscripts in the molecular formula is equal to three. 

No more than two of the subscripts can be equal, and your calculated value of 28 must be a whole number. 

So, CH(CFe)CHCHOO is your formula. 

However, CH(CFe)CHCHCO will also work because it fits all the requirements.

The accepted value for 1-diacetylferrocene is CH(CFe)CHCHCO or CH(CFe)CHCHCOO. 

7. Calculate the molar mass of 1-diacetylferrocene. 

The sum of your subscripts is 28, which is a whole number. 

Your calculated value for the molar mass is 264 g/mol. 

Since no more than two of your subscripts can be equal, and since the molecular formula you obtained in number 6 is CH(CFe)CHCHCO,(not CH(CFe)CHCHCO,) and since there is no H on the molecule, you must have made a mistake in some step.

When you put them into an organic chemical database, they show that number 6 has a molar mass of 264 g/mol.

8. Calculate the mass of 1-diacetylferrocene per mole. 

The number in the subscript is a whole number, so you do not have to calculate the units of mass. 

You have to calculate the mass in grams, so you have to convert your units from s to g by dividing by the atomic mass of carbon. 

The number you get will also be a whole number, so there will be no rounding error.

9. Calculate the molecular volume of 1-diacetylferrocene or CH(CFe)CHCHCO. 

There are 30 s-atoms per molecule, and one molecule is completely surrounded by eight C2 atoms. 

The molecule has a volume of 0.758 cm3. 

Your calculated value for the molar volume of 1-diacetylferrocene or CH(CFe)CHCHCO is 0.758 cm3.

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