Experiment 13 Report Trottier 1

Name: Kaitlyn Trottier Partner: Ella Gronlund

Student No: 20430175 Student No: 20407164
Lab Section: 015 Bench # (on computer screen): 11

Experiment 13 (2 weeks) (LSM) Metal Acetylacetonate Complex

Purpose
The purpose of this lab is to gain hands-on experience with inorganic synthesis methods through
the preparation of the tris(acetylacetonate) iron (III) metal complex. During the second week, the
focus will shift to recrystallizing the complex, determining its melting point, and recalculating
the percent yield based on the refined product.

Introduction
In this experiment, a coordination complex is produced through a Lewis acid-base reaction,
where ligands form coordinates covalent bonds. A ligand is an ion or molecule that donates a
pair of electrons to the central metal atom or ion to form a coordination complex, 2 thus having
one or more pairs of electrons to donate. These ligands, also referred to as complexing agents, 3
engage with metal ions capable of accepting electron pairs. 4

Acetylacetone can ionize to form an acetylacetonate anion. 1 Due to this anion’s resonance
stability, it acts as a Lewis base capable of coordinating with metal ions. In our experiment,
acetylacetonate ions will coordinate with iron (III) ions to create an octahedral Fe(acac)3
complex.1

This lab also employs recrystallization to refine and purify the synthesized product. Initially,
rapid crystallization can trap impurities within the crystals, resulting in poor formation. To
counter this, near-equilibrium conditions at the saturation point between the solid and dissolved
states of the product. So, it is re-melted and cooled. By cooling the solvent, the equilibrium
shifts, allowing for the gradual formation of crystals. Slow cooling is key to ensuring impurities
are excluded and remain in the solution.1

Procedure
Synthesis of Fe(acac)3
Gloves MUST be worn throughout the experiment.

1. Set up the snorkel above the work area.

2. Make an ice bath in a 600 mL beaker. Then place a 150 mL beaker filled with
approximately 150 mL of RO water in it.
3. Measure 1.00g of FeCl3*6H20 on a top-loading balance and transfer it into a 125mL
Erlenmeyer flask.
4. Pour 15 mL of RO water into the flask.
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5. Place the flask on a hot plate and add a stir bar. Set the device to sir, but do not turn
on the eat.
6. In the fume hood, measure 2 mL of acetylacetone into a 50 mL beaker using a
dispensette. Swirl Gently.
7. Slowly add the acetylacetone solution to the flask containing the iron chloride
solution using a Pasteur pipette.
8. Weigh roughly 2.5g of sodium acetate and dissolve in about 10 mL of RO water in a
50 mL beaker. Transfer the solution to the red mixture using a Pasteur pipette while
stirring vigorously until crystals form.
9. Heat the mixture to between 72 and 80 degrees Celsius for ten minutes on a hot plate.
10. Turn off the heat and remove the flask from the hot plate.
11. Cool to room temperature (approx. 10 mins)
12. Meanwhile, set up the vacuum filtration system.
13. Filter the product using the vacuum filtration system and wash four times with 15mL
of ice-cold RO water, then leave to air dry.
14. Transfer the dry product, along with the filter paper, into a watch glass for weighing.
15. Discard filter paper in the designated container and store the solid product in labeled
beakers.
Recrystallization of Fe(acac)3
1. Place a snorkel over the workstation.
2. Set up two hot water baths: one in a 600 mL beaker and 150 mL for the other. Heat
both to just above 70 degrees Celsius, then turn off the heat.

3. Add 0.3g of the previously prepared product to the 50 mL beaker. Submerge in the
150 mL hot water bath.

4. Dispense 10 mL of methanol into a 150 mL beaker. Put this in the 600 mL beaker hot
bath.
5. Now, recrystallize the product by gradually adding 2mL of the heated methanol using
a Pasteur pipette until it dissolved. Then, place it in a hot water bath to partially
evaporate the methanol, Remove and let cool on the bench.
6. After the solution is cooled, place the beaker in the ice bath for 10 minutes.
7. Cool 5mL of methanol in the other ice bath.
8. Set up the vacuum filtration system, breaking up large crystals with a stir rod. Then,
rinse the sides of the beaker with the chilled methanol and pour it into the filtration
system with the rest of the product.f
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9. Leave the product to air dry until powdery on the filtration system.

10. Record the mass of the watch glass before and after transferring the dry product onto
it, using a top-loading balance for accuracy.

11. Use the Mel-Temp apparatus to record the melting points of both the crude and pure
products.
[For more information, see Queen’s First Year Lab Manual 1]

Observations
Part One:
Ferric chloride hexahydrate exhibited a mustard yellow hue, a slight sheen, and a crystal-
like appearance, proving difficult to pulverize. Acetylacetone, on the other hand, was clear, of
low viscosity, and emitted a strong, unpleasant odor that persisted even within the confines of a
fume hood. The addition of acetylacetone to ferric chloride immediately resulted in a vivid
transformation to a deep, blood-red color with brownish tints, maintaining its strong odor and
becoming more viscous before heating, while the solution turned translucent. Sodium acetate,
clear and shiny with a crystal-like form, dissolved readily in water, forming a uniform solution.
Upon its introduction to the mixture, the scent intensified, and the color shifted to an opaque,
light red, accompanied by foaming and crystallization. Heating expedited crystal growth,
thickening the solution. The final product, post-filtration, resembled sticky, dark red mud,
transitioning to a dry, clay-like texture that was challenging to handle.

Part T wo:
The initial crude product displayed a red hue with orange undertones, possessing the
consistency and opacity of dried clay, along with a brittle nature. Methanol, clear and of low
viscosity, carried no scent. During the recrystallization process, the addition of methanol
transformed the product into a deep red, transparent liquid without any solid crystals, indicating
full solubility. As the solution was heated and the methanol began to evaporate, the mixture
thickened, retaining its deep red color, and crystal formation was evident. Upon removal from
the heat, crystallization rapidly proceeded with most of the methanol evaporated. During
filtration, the crystallized product showcased a deep red color with patches of black, featuring a
shiny, opaque, and brittle appearance. The final recrystallized product was a red, slightly shiny
powder. When melting, both the crude and pure products exhibited a unique phenomenon with a
bright green light appearing beneath them, with the crude product melting sooner than the pure
one.
Crude Fe(acac)3

Mass of FeCl3∙6H2O: 1.03g

Mass of watch glass (with paper): 54.49 g

Mass of watch glass and crude product: 56.89g

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Recrystallized Fe(acac)3

Mass of watch glass (and paper): 34.43g

Mass of watch glass and pure product:34.55g

Melting point range for pure product: 179.0 -186.5 oC

Melting point range for crude product: 175.0 – 185.0 oC

Calculations
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Questions
From Part I

1. What is the limiting reagent?

The limiting reagent is the Ferric chloride hexahydrate.
2. What is the percent yield of the crude product?
The percent yield of crude product is 178%.
3. Give three reasons why you did not get 100% yield.
 Incomplete reactions: caused by the impurities in the products forming.
 Poor top-loading balance calibration: it is possible that the balance was not calibrated
properly, or a participant forgot to initially tare.
 Despite our best efforts, the product retained liquid, causing it to have a clay-like
texture. This added liquid increased the mass significantly.
From Part II
4. What is the percent yield of the pure product?
The percent yield of pure product is 5%.
5. Compare your crude vs. pure product yield. List three reasons why they may be
different/the same.
 The flasks used were rather wet, causing the product to stick to the glass. Even when
rinsing with methanol, the product was sticking to the beaker so much, that it was
extremely difficult to get it out.
 Vacuum Filtration System: our recrystallized product seeped through the edges of the
filter paper, due to improper position caused by human error. This was evident from
the little specs of red inside the Erlenmeyer flask.
 Human error: one of the lab participants involved dropped the watch glass and paper,
causing some of it to go flying.

6. What can you say about the difference, if any, between the crude and the recrystallized
product in your observed melting point data?
This is likely because of the presence of stronger intermolecular forces in the recrystallized (no
impurities), compared to the crude product. This makes the substance more stable, leading to an
increase in the boiling point.
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References
1. Department of Chemistry. “First-Year Laboratory Manual”. Queens University. 2023-
2024. Print.
2. BYJU'S. (n.d.). Ligands - Definition, Types & Examples. Retrieved March 21, 2024,
from https://byjus.com/jee/ligands/
3. LibreTexts. (2023, April 12). 17.4: The Formation of Complex Ions. In General
Chemistry: Principles, Patterns, and Applications (Averill). Chemistry LibreTexts.
https://chem.libretexts.org/Bookshelves/General_Chemistry/Book%3A_General_Chemist
ry%3A_Principles_Patterns_and_Applications_(Averill)/17%3A_Solubility_and_Compl
exation_Equilibria/17.04%3A_The_Formation_of_Complex_Ions 4.
4. LibreTexts. (2023, January 30). Lewis Concept of Acids and Bases. In Supplemental
Modules (Physical and Theoretical Chemistry). Chemistry LibreTexts.
https://chem.libretexts.org/Bookshelves/Physical_and_Theoretical_Chemistry_Textbook
_Maps/Supplemental_Modules_(Physical_and_Theoretical_Chemistry)/Acids_and_Base
s/Acid/Lewis_Concept_of_Acids_and_Bases