Synthesis of Tetramethylammonium Triiodide

Kimmy Pathanasap (5861052)

Supichaya Nobnom (5861155)
Pichayathida Siriwechdaruk (5861105)
Pnotporn Jantarakolica (5861115)
Passawas Satitjindawong (5861095)

Advance Chemistry 1102

Ms.Patraphorn Sanguansat
Mahidol University International Demonstration School
Semester 1 Academic year 2016-17

Synthesis of Tetramethylammonium Triiodide

Introduction
All molecules have chemical structure. They appear in three dimensional geometric shape
or configuration which are unique in each types of molecules. Chemical structure tells us the
arrangement of chemical bonds between atoms in a molecule. It is shown using symbols that
represent elements and lines which joins each atom together. One line between atoms shows that
they have a single bond between them. Hence, two lines show double bonds and three lines show
triple bond. Structure determination can be applied from very simple molecules, like oxygen and
nitrogen, to very complex ones like protein and DNA. One atom can have two to four bonding
partners. Therefore, if they have two bonding partners, their chemical structure will be in a linear
structure. However, with three and four bonding partners, their structure will be changed to
trigonal and tetrahedral. From this information, scientists had done experiments and discovered
that if a molecule reacts with another molecule, the product that will be achieved will result
forming a new molecule with different structure. We call this process chemical reaction. In
order to understand a chemical reaction, chemical equation is an important topic that we must
understand. Chemical equation represents chemical reaction in form of symbols and formulas. In
a formula, the reactant will be on the left side of the equation containing an arrow after it to
separate it from the product which will be located on the right side of the equation. A chemical
equation undergoes the law of conservation of mass which states that Atoms cannot be created
or destroyed. This then proves that there will always be the same amount of atoms in both the
reactant and the product. According to the previous statement, we have to know how to balance
an equation.
The purpose of this experiment is to form crystal using tetramethylammonium iodide
with iodine, to find limiting reagent of this chemical reaction and also %yield. To calculate the
percentage yield, the mass of the actual product (actual yield) in grams is being divided by the
theoretical mass of the product (theoretical yield) in grams, meaning that it has been calculated,
and times by 100 to get the percentage:

Synthesis of Tetramethylammonium Triiodide

Sometimes we get to know the moles of the substances rather than grams. We have to be
able to change from moles to grams. Mole is a unit of measurement of the amount of substances.
One mole has the amount of atoms equal to the atoms of carbon-12. To convert moles to grams
we need to use a formula:

The actual yield is always lesser or equal to the theoretical yield. In this experiment we
will use precipitation method which is the creation of a solid from a solution. When a reaction
occur in a solution, solid is formed called a precipitate. The chemical that causes the solid to
form is called the precipitant. We also have to use vacuum filtration which is a technique to
separate solid product from a solvent. This experiment will allows us to understand more about
chemistry.

Synthesis of Tetramethylammonium Triiodide

Experiment
Materials:
1. Tetramethylammonium iodide ( M e 4N +I )
2. Iodine ( I 2 )
3. 95% Ethanol ( C 2H 5OH )
4. Hexane ( C 6H 14 )
Laboratory Apparatus:
1. Cylinder
2. 50 mL beaker
3. Lab Spatula
4. Weighing Paper
5. Stirring Rod
6. Hot Plate
7. Ice Bath
8. Bchner Funnel
9. Filter Paper
10. Watch Glass
11. Electronic Balance
12. Capped Vial
Experimental Method:
1. Add 0.5 g of tetramethylammonium iodide to a 50 mL beaker, then use a stirring rod to
break up any clumps present.
2. Add 0.6 g of iodine and 12 mL of ethanol into the beaker.
3. Place the beaker onto the hot plate under the fume hood and slowly stir the solution until
tetramethylammonium iodide has completely dissolved.
4. To prevent the crystal from forming, make sure that the solution is heated with low
temperature. The total time spent on the hot plate is about 10 minutes.
5. Then, remove the beaker from the hot plate and allow it to cool down on its own.
(Agitating the solution can cause small crystals to form other impurities.)
6. The crystals will start to form inside the beaker.
7. Once the solution has reached the room temperature, place the beaker in the ice bath for
about 10 minutes. During this time, set up the equipment of the suction filtration, which
will be used later for filtrating and washing the compound.
8. Using vacuum filtration, collect the crystals and wash them with hexane. Wash until the
filtrate dropping is colorless.
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Synthesis of Tetramethylammonium Triiodide

9. Air-dry the product overnight and weigh.

10. Hand in the sample in a capped vial with labelled name, compound name, and date.

Synthesis of Tetramethylammonium Triiodide

Result and Discussion

The product obtained from doing the experiment is as shown below. The pictures below shows
the crystals, both with and without using the microscope.

Figure 1. The product after being filtered (before air dried)

Figure 3. Product (purple crystal) as seen under

the microscope (Tetramethylammonium Triiodide).

Figure 2. The product after being air dried overnight.

Figure 4. Product (Green crystal) as seen under

The microscope (Tetramethylammonium Pentaiodide)

Synthesis of Tetramethylammonium Triiodide

Observations
After finish synthesizing the crystal, it could be seen that most of the crystal obtained is
purple in color and the crystal are in the shape of rod. The crystals which are purple color dont
stick hold onto each other or clump. Most of the large purple crystals are on the center of the
filter paper, while the small crystals scatter all around the filter paper. Some of the crystal are
green in color. The green color crystal also in the form of flakes, and some of them are really
small, almost powder-like in shape. They mostly stick together into clumps. Both the green
crystal and the purple crystal reflects light, but the purple crystals are more transparent compared
to the green crystals. The amount of the green crystals before air drying (Figure 1.) is less than
when the crystals got air dried overnight (Figure 2).
Under the microscope, it could be seen that the purple crystals (Figure 3.) are bigger in
size, the crystals are long, rod-like in shape. The crystals are partly transparent. The ability to
reflect light of the crystal is lesser than the green crystal. While the green crystals (Figure 4.)
sticks together, forming spherical-like shape.The green crystals are better at reflecting light,
appearing white/silver-like in color under the microscope from its ability to reflect light.
When being compared to Tetramethylammonium Pentaiodide, it could be concluded that
the green crystal which was mixed in our product, is Tetramethylammonium Pentaiodide. In the
tables below (Table 1 & Table 2), the Tetramethylammonium Triiodide refers to the total
product, meaning the Tetramethylammonium Triiodide with the Tetramethylammonium
Pentaiodide.
Also, we know from this lab experiment that tetramethylammonium can react with iodide
and produce a product, which is a polar solid crystal. We know that the product,
tetramethylammonium triiodide is polar since we use hexane, which is non-polar, to rinse off the
excess ethanol, which have a nonpolar region, from the crystal. The crystal didnt dissolve from
being in contact with hexane, which means that it is polar.
Table 1: Amount of substances used in the experiment; both in grams and moles.
Substance

Grams

Mole

Tetramethylammonium Iodide

0.50

2.5 x10 3

Iodine

0.61

2.4 x 10 3

Tetramethylammonium
Triiodide

1.1

2.5 x 10 3

Note: For calculations used in this table, see appendix A-B. All of the numbers presented are in significant figures.

Synthesis of Tetramethylammonium Triiodide

Table 2: Amount of substances as calculated theoretically and as weighted during the lab
Tetramethylammonium
iodide

Iodine

Tetramethylammonium
triiodide

Theoretical

0.50 g

0.61 g

1.09 g

Actual

0.50 g

0.61 g

0.78 g

Note: For calculations, see appendix C. All of the numbers presented has been rounded into 2 decimal places.
Discussion
The chemical equation used in this experiment is M e 4N +I + I 2 Me 4N +I 3 . It
means that one mole of tetramethylammonium iodide reacting with one mole of iodine will result
in one mole of tetramethylammonium triiodide. The number in front of each chemical formula of
a balanced chemical equation will indicate the amount of mole of the substance with that
chemical formula. If the number in front of the chemical formula is one, it could be omitted.
In this lab experiment, the limiting reagent/reactant is iodine. From calculating the mole
of iodine (Appendix B) and tetramethylammonium iodide (Appendix B), it could be seen that the
amount of iodine, in mole, is lesser than the amount of tetramethylammonium iodide. It means
that iodine would be used up before all of the tetramethylammonium will be used. The excess
reagent/reactant present in the lab is the tetramethylammonium iodide. It means that there will be
some tetramethylammonium iodide left, unused. From the calculation (Appendix D), it could be
seen that there would be about 0.0169 g of it left, unused.
To determine the efficiency of the reaction done in the lab experiment, percentage yield
is being calculated. In this lab, the percentage yield calculated is 71.55% (Appendix E). It means
that throughout the process, 28.45% of the product has been lost.
There are many possible errors that had been done throughout the experiment, which
caused the loss of product and impurities. First, when the reagents were being weighed, there
might be some errors like the wind from the air condition, or someone push the table that the
balance is on, which might cause the weight of the substance on the balance to change. Second,
when the mixture is being stirred on the hot plate, stirring too hard might cause the mixture to be
stuck on the side of the beaker, resulting the loss of the product. Also, the small crystals might
have been caused by the quick change of temperature. If the solution had been left to cool down
in room temperature for a longer period of time, then the crystals might be bigger. Moreover, the
Bchner Funnel has been shared for the groups that synthesis tetramethylammonium
pentaiodide, which might caused the product to have some of the said substance mixed and some
of the equipments used might not be cleaned, which might cause impurities.
To improve this experiment, all of the equipments used must be checked that it was clean
properly to avoid any errors. Also, more time is needed in order to get larger crystals and to be
ensured that the steps of the procedures were being followed properly to avoid any errors.
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Synthesis of Tetramethylammonium Triiodide

Conclusion
To sum up, we react tetramethylammonium iodide with iodine to synthesize
tetramethylammonium triiodide. We were successful in making the crystal. From this
experiment, we were able to find out that iodine is our limiting reagent and
tetramethylammonium iodide is our excess reagent. Based on our data, our percentage yield in
this experiment is 71.55%. This experiment allows us to use our knowledge in finding moles,
weight of substances and percentage yield, and apply it in real life.

Synthesis of Tetramethylammonium Triiodide

Reference
1. (n.d.). Chapter 2 Molecules, Ions, and Chemical Formulas. Retrieved November 09,
2016, from
http://2012books.lardbucket.org/books/principles-of-general-chemistry-v1.0/s06-molecul
es-ions-and-chemical-fo.html
2. Ethanol | CH3CH2OH - PubChem. (n.d.). Retrieved November 09, 2016, from
https://pubchem.ncbi.nlm.nih.gov/compound/ethanol
3. Hexane. (n.d.). Retrieved November 9, 2016, from
https://pubchem.ncbi.nlm.nih.gov/compound/8058#section=Top
4. Iodine. (n.d.). Retrieved November 9, 2016, from
https://pubchem.ncbi.nlm.nih.gov/compound/807#section=Information-Sources
5. (n.d.). Molecular Structure & Bonding. Retrieved November 09, 2016, from
https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/intro3.htm
6. Reaction Equations. (n.d.). Retrieved November 09, 2016, from
http://www.science.uwaterloo.ca/~cchieh/cact/c120/reaction.html
7. Tetramethylammonium Iodide. (n.d.). Retrieved November 9, 2016, from
https://pubchem.ncbi.nlm.nih.gov/compound/Tetramethylammonium_iodide#section=To
p
8. TETRAMETHYL AMMONIUM TRIIODIDE. (n.d.). Retrieved November 9, 2016,
from https://pubchem.ncbi.nlm.nih.gov/compound/25022202#section=Top

Appendices
Appendix A- appendix E shows the calculations used in this experiment. It includes
converting the substance from grams into moles, calculation for the leftover reactants, and
calculation for percentage yield to determine the efficiency of the reaction done in the
experiment. The information from appendix A to appendix E has been used within the result and
discussion and conclusion section of this lab report. Also, appendix F to appendix J shows
additional information about the substances used within the experiment.
Appendix A: Conversion of 0.50 g Me 4N +I into moles
0.50 g Me 4N +I x

1 mol Me 4N +I
201.0 g Me 4N +I

= 0.002487562189 mol Me 4N +I

Appendix B: Conversion of of 0.61g I 2 into moles

1 mol I

0.61 g I 2 x 253.8 g I22 = 0.002403467297 mol I

Synthesis of Tetramethylammonium Triiodide

Appendix C: Calculation for amount of M e 4N +I

0.002487562189 mol Me 4N +I

454.8 g Me 4N +I 3
1 mol Me 4N +I 3

= 1.131343284g Me 4N +I

Appendix D: Calculation for the amount of the leftover M e 4N +I

( 0.002487562189 mol Me 4N +I - 0.002403467297 mol M e 4N +I ) x

= 0.01690307329 g Me 4N +I

201.0 gMe 4N +I
1 mol Me 4N +I

Appendix E: Calculation for the percentage yield

Actual yield
% yield = Theoretical
yield x 100%
= 0.78
1.09 x 100%
= 71.55 %
Appendix F: Additional information about tetramethylammonium iodide
Other Names: Artilacer, Banikol, Yodurtan
Chemical Formula: M e 4N +I or C 4H 12IN
Molecular Weight: 201.0 g/mol
Appearance: White powder
Polarity: Polar

Figure 5. Chemical structure of tetramethylammonium iodide

Appendix G: Additional information about iodine

Other Names: Vistarin, Iodine crystals, Tincture iodine
Chemical Formula: I 2
Molecular Weight: 253.8 g/mol
Appearance: Blue-ish or purple crystals
Molecular Shape: linear
Polarity: Non polar

Figure 6. Chemical structure of Iodine

Appendix H: Additional information about ethanol

Other Names: Ethyl alcohol, Alcohol
Chemical Formula: C H 3CH 2 OH or C 2H 6O
Molecular Weight: 46.07 g/mol
Appearance: Clear, colorless liquid
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Synthesis of Tetramethylammonium Triiodide

Polarity: Have both polar and nonpolar region

Figure 7.
Chemical structure of ethanol

Appendix I: Additional information about Hexane

Chemical Formula: C 6H 14
Molecular Weight: 86.18 g/mol
Appearance: Clear, colorless liquid with petroleum-like odor
Polarity: nonpolar

Figure 8. Chemical structure of Hexane

Appendix J: Additional information about tetramethylammonium triiodide

Other Names: Tetramethylazanium triiodide
Chemical Formula: M e 4N +I 3 or C 4H 12I 3N 2
Molecular Weight: 454.8 g/mol
Appearance: Purple-ish colored, rod-like shaped crystals
Polarity: polar

Figure 9. Chemical structure of tetramethylammonium triiodide

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