Jane Doe
Lab Partner-
3.1.2022, CHEM 3106-500
TA-
Experiment 5: Friedel-Crafts Acylation of Ferrocene
Purpose:
Students will be able to perform and describe Friedel-Crafts reactions, performing extractions, filtration
techniques, and view thin-layer chromatography to characterize the product.
Reactions and Physical Properties Table:
Reagents MW g/mol Density amount mmol Bp (C°) Mp (C°)
and g/mL
Solvents
AlCl3 133.34 - .17g .023 - 192.6
Acetyl 78.49 1.10 90µL .007 52 -
chloride
ferrocene 186.04 - .12g .65 - 172.5
CH2Cl2 84.93 1.33 4mL - 39.6 -
Safety:
Calcium chloride (Warning)
o Risk Factors:
May form combustible dust concentrations in air
Causes serious eye irritation
o Safety Factors:
Wash face, hands and any exposed skin thoroughly after handling
Wear eye/face protection
Sodium hydroxide, 25% (Danger)
o Risk Factors:
May be corrosive to metals
Causes severe skin burns and eye damage
May cause respiratory irritation
o Safety Factors:
Keep only in original container
Do not breathe dust/fumes/gas/mist/vapors/spray
Wash face, hands and any exposed skin thoroughly after handling
Use only outdoors or in a well-ventilated area
Wear protective gloves/protective clothing/eye protection/face protection
Dichloromethane (Danger)
o Risk Factors:
Causes skin irritation
Causes serious eye irritation
May cause drowsiness or dizziness
May cause cancer
May cause damage to organs through prolonged or repeated exposure
o Safety Factors:
Obtain special instructions before use
Do not handle until all safety precautions have been read and understood
Use personal protective equipment as required
Wash face, hands and any exposed skin thoroughly after handling
Wear eye/face protection
Do not breathe dust/fume/gas/mist/vapors/spray
Use only outdoors or in a well-ventilated area
Acetyl chloride (Danger)
o Risk Factors:
Highly flammable liquid and vapor
Causes severe skin burns and eye damage
o Safety Factors:
Do not breathe dust/fume/gas/mist/vapors/spray
Wash face, hands and any exposed skin thoroughly after handling
Wear protective gloves/protective clothing/eye protection/face protection
Keep away from heat/sparks/open flames/hot surfaces
Keep container tightly closed Ground/bond container and receiving equipment
Use explosion-proof electrical/ventilating/lighting equipment
Use only non-sparking tools
Take precautionary measures against static discharge
Use only outdoors or in a well-ventilated area
Keep cool
Wear respiratory protection
Aluminum chloride (Danger)
o Risk Factors:
Causes severe skin burns and eye damage
May cause respiratory irritation
o Safety Factors:
Do not breathe dust/fume/gas/mist/vapors/spray
Wash face, hands and any exposed skin thoroughly after handling
Wear protective gloves/protective clothing/eye protection/face protection
Use only outdoors or in a well-ventilated area
Ferrocene (Danger)
o Risk Factors:
Flammable solid
Harmful if swallowed
o Safety Factors:
Wash face, hands and any exposed skin thoroughly after handling
Do not eat, drink or smoke when using this product
Keep away from heat/sparks/open flames/hot surfaces. - No smoking
Ground/bond container and receiving equipment
Use explosion-proof electrical/ventilating/lighting equipment
Wear protective gloves/protective clothing/eye protection/face protection
Procedure:
1. Add a spin vain to the 5 mL conical vial. Weigh 0.170 g of anhydrous AlCl 3 using the
scale in the hood and transfer it to the 5 mL conical vial. Keep vial covered.
2. Add 2.5 mL of CH2Cl2 to the conical vial.
3. Add 90 microliters of acetyl chloride to the conical vial using a micro pipet in the hood.
4. Equip the conical vial with the Claisen adapter fitted with a drying tube containing CaCl 2.
This is a short reaction, so you do not need very much CaCl 2 in the drying tube.
5. Dissolve 0.120 g of ferrocene in ~1.5 mL of CH 2Cl2 and add the solution to the conical
vial through the straight neck of the Claisen head adaptor. Since the solution does not
need to be added slowly, it can be added with a pipet by temporarily taking the cap off
the Claisen head.
6. Take note of any visual changes to the reaction's appearance as it progresses and how it
relates to time from the addition of the ferrocene reagent.
7. Allow the reaction to proceed for 15 minutes
8. Carefully transfer the reaction mixture to a centrifuge tube containing 5 mL of ice water.
9. Cool the tube in a beaker of ice water.
10. Remove the organic layer and transfer it to a clean dry 50 mL Erlenmeyer flask or
container of similar size.
11. Extract the aqueous mixture with CH2Cl2 (3 x 3 mL) in the tube with shaking and venting
to encourage the mixing of the aqueous and organic phases.
12. Remove the organic layer after each extraction using a pipet and combine it with the
previous organic layers that are in the clean dry 50 mL Erlenmeyer flask or container of
similar size. The extraction mixture may need to be centrifuged if an emulsion forms.
13. Dry the organic solution using anhydrous MgSO 4 by adding small amounts covering the
tip of your spatula and swirling the solution. Once a portion of the added MgSO 4 no
longer clumps and remains free flowing the solution is dry.
14. Transfer the dried solution to a small dry container for solvent evaporation. The product
mixture will need to be removed from the container and saved for the next experiment so
choose your container wisely. The MgSO 4 may need to be filtered from the solution if
the solution can't be carefully decanted from the solid. Using a small piece of cotton in a
funnel or a pipet works well for filtering MgSO4 from the solution.
15. Use a hot plate and compressed air in the hood to evaporate all the solvent.
16. Remove the solid material from the container and transfer to a shell vial. Get a weight of
the crude product during this process. Weighing the vial by difference is one possible
way of doing this.
17. Label the vial containing the crude product. If you do not share a lab drawer with another
section your sample may be stored in your drawer. If you do share a drawer the sample
may be collected and stored in a well plate until next week.
18. Keep crude product for experiment 6
Data and Observations:
Materials:
.17g: Anhydrous AlCl3 - 13 mL:CH2Cl2 - 90 micro liters: Acetyl Chloride
120g: ferrocene
There was a color change of the solution from clear liquid to deep purple thick liquid, to
burnt orange liquid, and then a copper solid product
Calculations and Results:
Actual Yield:
4.2782 g (vial with product) - 4.177g (vial by itself) = .1012g = 101.2mg (actual amount of
product)
Theoretical Yield:
(.12g ferrocene / 186.04g/mol ferrocene) = .00064502 mol ferrocene
228.07g/mol = m.w of monoceytl ferrocene
(228.07g/mol monoceytl ferrocene) x (.00064502 mol ferrocene) = .1471g = 147.1mg
Precent yield:
(101.2mg (actual yield) / 147.1mg (theoretical yield)) x 100 = 68.80%
The precent yield at 68.8% means that the reaction produced the product and was successfully
completed.
Discussion/Conclusion:
In the experiment, a Friedel-Crafts reaction was done with AlCl3, Acetyl chloride, ferrocene, and
CH2Cl2 to perform a product then characterized by a thin-layer chromatography. The reaction was
performed by mixing AlCl3, Acetyl chloride, ferrocene, and CH2Cl2 for 15 minutes and extracting the
organic layers of the solution. After, lab groups added MgSO4 which was then filtered and evaporated to
result in copper solid product. There were no major issues or accidents during the experiment and the
group was able to extract .1012g at the end of the evaporation process. Along with the experiment going
smoothly, the precent yield was 68.8%, so the reaction was successfully completed, however this could
only be determined when preforming the TLC the following week.
Post Lab Questions:
1. What is an acyl group?
An acyl group has R-C=O
2. Design a synthesis for the compounds below using Friedel-Craft substitution chemistry.
Include the starting material and reagents needed for each.
A.
B.
C.
3. Explain why the treatment of ferrocene in this reaction yields two products and offer an
explanation as to why the species below does not form under the experimental conditions
described above
This is due to when the previous conditions go through a Friedel craft acylation, it will not go
through further acylation in same ring due to the electron density of the ring is reduced from the
first acylation, so diacylation in same ring is impossible.
