SYNTHESIS OF TETRAMETHYLAMMONIUM TRIIODIDE

Lab Report

Nutchanon Charnwutiwong
Sarisa Keittivuti
Pathitta Kittimongkolsuk
Vanessa Rujipatanakul
Chinorod Tavichai
Thanawin Ungkananuchat

Accelerated Chemistry 1101

Ms. Patraphorn Sanguansat
Mahidol University International Demonstration School
Semester 1 Academic Year 2017-2018
Abstract:
This experiment was done to demonstrate the process of crystallization, to determine the
percent yield, the moles of each compound and the amount of excess reagent, also, to
understand the chemical reaction and stoichiometry. The experiment is conducted by mixing
0.5g of Tetramethylammonium iodide with 12 mL of 95% ethanol and 0.6g of Iodine. Then
crystallize it by letting the solution cool down. After that, the crystal can be collected from the
method of vacuum filtration. In order to prevent the product from contamination, the crystal
should be washed with hexane. As a result of the experiment, the product is produced in a form
of green and dark purple rod-shape crystal weighed 0.95g. From observing the final product, it
can be seen that the product is contaminated.
Introduction:
Crystallization is a process in which a solid forms in highly organized structure. It occurs
when saturated solution, which is when the solute can’t be dissolved any more in that
temperature, is heated into supersaturated solution, which is when there are more undissolved
solutes than the saturated solution, and then getting cooled down causing the crystal seed to
start growing. Crystallization can also result from the precipitation as the solute in the cooled
down solution gather together forming the crystal. According to this, the Tetramethylammonium
Iodide and Iodine can form the crystal in the Ethanol solvent due to their chemical structure and
the properties of the solutes in which the chemical formula for Tetramethylammonium is Me4N+I-
and Iodide is I2.
The crystals from the crystallization can be seen in the shape of cubic, tetragonal,
hexagonal, and trigonal. In order to understand how crystal forms in the arrange pattern, we
need to know the chemical structure and chemical equation. For chemical structure, it is the
structure of the molecules or compound that determine how the atoms form a bond between
each other. Tetramethylammonium is one of tetrahedral geometry structures while Iodide is one
of linear structures. As for Tetramethylammonium Iodide, it has two separated structure which is
tetrahedral and trigonal planar. However, when these compound and molecule combine
together, the structures merge and transform into a new structure. In addition, chemical
equation is also important in finding the chemical structure of the product. The chemical
equation is the symbol using the chemical formula to represent the chemical reaction.
 In chemical equation, there is two side which is the left side, before the arrow, and the
right side, after the arrow. The left side is the reactant or the substance that will turn into the
product by the process of combination, decomposition or replacement. The right side is the
product formed after the reaction is finished. When we work out the chemical equation, we need
to consider about balancing the equation in order to be able to precisely determine the ratio of
mole in each compound in the reaction. If we don’t balance the equation, the mole of the
product and reactant can be miscalculated. To balance the equation, both sides need to have
an equal amount of each element. For example, if the reactant have 3 atoms of Iodine, then the
product also need to have the same number of atoms of Iodine.
Balancing the equation and calculating the mass of the product by the given mass of
each reactant can give the result of the theoretical yield, which is the mass of product if the
reaction occurs 100%. This is because we can calculate the mass of the reactant in form of
mole, a unit of measurement of the amount of substance. The mole of each compound in the
𝑚𝑎𝑠𝑠
equation can be calculated by using the formula 𝑚𝑜𝑙𝑒𝑐𝑢𝑙𝑎𝑟 𝑤𝑒𝑖𝑔ℎ𝑡. Nevertheless, in reality, it is

very rare for the exact yield to occur since there are some factors that reduce the ability of
reaction to complete 100%. The actual yield can be found only when doing the experiment and
it is usually less than the theoretical yield. It is rarely equal to the theoretical yield. Therefore, the
actual yield divided by theoretical yield and multiply by 100 is equal to the percent yield of the
reaction.
Objective:
- To learn and understand more about crystallization.
- To do the calculations such as calculating the percent yield, moles of each compounds,
and amount of excess reagent.
- Understand/Demonstrate about Stoichiometry: mole, excess reagents, limiting reagents,
etc.
- To observe the chemical reactions.
Experiment:
- Material:
- Tetramethylammonium Iodide (0.5 g)
- Iodine (0.6 g)
- 95% Ethanol (12 mL)
- Hexane
- Equipment:
- Büchner Funnel
- Büchner Flask
- Petri Dish
- Watch Glass
- Filter Paper
- Weighing paper
- Hot Plate
- Stirring Rod
- Magnetic bar
- 50 mL Beaker
- Graduated Cylinder
- Dropper
- Vacuum Pump
- Ice Bath
- Scale
- Timer
Procedure:
Result:
- Physical Appearance: After we synthesize the tetramethylammonium triiodide, the
product we get are in the form of green and dark purple rod crystal. Most of the products
we can see on the filter paper are the purple rod crystals. They are mostly scattered
around the paper without getting clumped together. On the filter paper, there are only
some spots in the center and the area of the products that the crystals are in the form of
green rods. The green rods are similar to the dark purple rods as they are not getting
clumped together. The crystals we get, both dark purple and green rods, are shiny and
they reflect light very well.
- Amount of the product we get: After subtracting out the mass of the filter paper, we get
the products with the mass of 0.95 g.

The final product we get after letting the

product rest overnight: dark purple and green
rod-shape crystals.
Analysis:
Our product is not really accurate due to the error caused during the process of
measuring the weight of the reactants. To be more precise, we used 0.51 g of
Tetramethylammonium Iodide instead of exactly 0.5 gram, also, the Iodine which we used 0.61
gram instead of 0.6 g. From that error, some of our product came out with the color of dark
purple, which is the result we want as our product should be Tetramethylammonium Triiodide.
But some of them are in green, which is the color of Tetramethylammonium Pentaiodide. It can
be inferred that the reaction occurred in our
experiment exceed the stage we intend to
create.

We can see that there is already some green

color since we mixed all the materials together in
the beaker.

Discussion:
1. Calculate the number of moles of each compound
Equation of synthesis of tetramethylammonium triiodide

Me4N+I- + I2 ----------> Me4N+I3-

Iodine:
𝑔
mol = 𝑀𝑤
0.61
= 126.90

= 0.0048 mol

Me4N+I-:
𝑔
mol = 𝑀𝑤
 0.51
=
201.051

= 0.0025 mol

(We find the moles of each compounds, using it mass that is prepare for the experiment
divided by their molecular weight.)
2. Indicate the limiting reagent and excess reagent
I2:
0.61 g 1.827 g (Excess reagent)

÷ 126.90 ×
380.625

0.0048 mol 0.0048 mol

Me4N+I-:
0.51 g 0.95 g
(Limiting reagent)

÷ 𝟐𝟎𝟏. 𝟎𝟒𝟗𝟑 × 380.625

0.0025 mol 0.0025 mol

From the calculation above, it can be seen that Me4N+I- or

Tetramethylammonium Iodide is the limiting reagent, since it gives smaller amount of
product comparing to the I2 or Iodine. Therefore, Me4N+I- is limiting reagent while I2 is
excess reagent.

3. Express the amount of excess reagent remaining

The amount of I2 that is used in the reaction
= mole of limiting reagent ×molecular weight of excess reagent
= 0.0025 × 126.90
= 0.317 g
The amount of excess reagent remaining
= the amount of excess reagent - the amount that is used in the reaction
 = 0.61 - 0.317
= 0.293 g
Therefore, the amount of excess reagent remaining is 0.293 g after the reaction
4. Discuss the % yield
𝑎𝑐𝑡𝑢𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
% yield = 𝑡ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑 × 100
0.95
= 0.95 × 100

= 100%

We get 100% which mean throughout the experiment, there is none of product lost.
5. Error
As we can see from the product’s color, it is noticeable that our product is not
accurate. To be more precise, the crystal that is produced from our experiment contains
some green instead of complete dark purple color. This error might be caused by the
amount of reactants that we measured, which both of the reactants, I2 and Me4N+I-, is
0.01g more than it should be and it might cause the reaction exceed to the higher level
of reaction.
Conclusion:
To conclude, we properly followed the step of putting together Tetramethylammonium
Iodide, Ethanol, and Iodine to make Tetramethylammonium Triiodide crystals. However, our
crystals were contaminated since the step of mixing the materials. Though, with that being said,
our percent yield is 100% which is surprising. It might be because limiting reagent,
Tetramethylammonium Iodide, and excess reagent, Iodine, which we used in the experiment
are not exact with the specified amount. This lab experiment makes us be able to apply the
knowledge we got from our classroom about Stoichiometry, and use it in real life.

Suggestion:
In the next experiment, we will try to be more accurate on measuring the materials.
These errors might come from the air which affect the mass of the materials. We will also be
more careful in each steps of the experiment. For example, we might break the materials finer,
try not to shake the beaker during the ice bath process, and try not to break the crystals in the
filtering method. In the experiment, the actions mentioned might influence how the reactants
reacted on each other which will give different forms of results.
References:
1. Crystallization. (n.d.). Retrieved November 28, 2017, from
http://www.reciprocalnet.org/edumodules/crystallization/
2. Clark, J. (2012). MOLECULAR STRUCTURES. Retrieved November 29, 2017, from
https://www.chemguide.co.uk/atoms/structures/molecular.html
3. PubChem. (2017). Tetramethylammonium iodide. Retrieved December 03, 2017, from
https://pubchem.ncbi.nlm.nih.gov/compound/Tetramethylammonium_iodide#section=2D-
Structure
4. Chang, R., & Goldsby, K. (n.d.). Mass Relationships in Chemical Reactions. In
Chemistry (pp. 76-117).
5. Helmenstine, P. A. (n.d.). What Is Percent Yield? Review Your Chemistry Concepts.
Retrieved December 04, 2017, from https://www.thoughtco.com/definition-of-percent-
yield-605899

Work log:

Members Work

Nont Experimenting, Material, Objective,

Calculation, Suggestion, Conclusion

Earn K. Experimenting, Discussion, Calculation,

Decoration

Van Experimenting, Objective, Abstract,

Introduction, Result, Analysis, Conclusion

Namo Experimenting, Abstract, Flow chart

Chino Experimenting, Introduction, References

Fahlan Experimenting, Editing