Accelerated Chemistry

Synthesis of Tetramethylammonia Triiodine

Lab

27 November 2017

Group Members:

Nattha Pongplanchai 5961014

Poondarik Tayawitit 5961086
Kanokpon Nagavajara 5961125
Voropol Leelarit 5961160
Parewa Pichayamarin 5961225
Abstract

The goal of this experiment is to synthesize Tetramethylammonium Triiodide, with the expectation of
producing the purest crystal, using Tetramethylammonium Iodide ( N (CH 3 )4 I 3 ) and Iodine ( I 2 ). The
occupation demonstrates how each mole of each reactant combined in the chemical reaction to
produce certain amount of product, which exhibits mass relationship and the law of conservation of
mass. It also demonstrates the position of the limiting factor, which has the effect on the determined
yield of the product. The limiting reagent is Iodine and the excess reagent is Tetramethylammonium
Iodide. The Tetramethylammonium Triiodide produced first by mixing the reactants until the mixture
is completely dissolve to be a homogeneous solution. Then increase its temperature and later on lower
the temperature for performing crystallization, following by filtering the crystal. Lastly, wash the
crystal with hexane and dry it overnight. The crystal resulted in dark purple small rod-shaped flakes.
The percentage yield is 86%, which the actual yield is 0.92 grams, the theoretical yield is 1.07 grams,
and the amount of excess reagent remaining is 0.475 grams.
Introduction

Imagine you are now going to make a red velvet cake to celebrate in your little sister’s
birthday party. The first thing that you have to do is to follow the steps in the recipe; putting the exact
amount of ingredients needed into the bowl. The ingredients that you need might be 1 cup of
buttermilk, 2 eggs and 1 teaspoon of vanilla extract. The correct balance of ingredients is what makes
food taste good. This is the same when it comes to Chemistry. Chemical reaction resembles when
we’re cooking. It is a chemical change that occurs through the interaction of two or more substances
to form a new substance. The chemical structure of molecules also changes when undergoing
chemical reaction. This is because chemical bond are made or broken apart to create a new molecule
(Chemical Reactions, n.d.). Chemical structure indicates the arrangement of chemical bonds between
atoms in a molecule, as well as the type of bond that formed. For instance, a single line between atoms
points out a single bond. Two lines denotes double bond and three lines represent triple bond.
Moreover, the chemical structure can determine the molecular geometry of the molecule. If there is
six bonding partners in the molecule, it will result as Octahedral structure, achieving all 90º angles
between each atom. In order to perform the chemical reaction, we need to fundamentally comprehend
the chemical equation. Chemical equation is generally the simpler or short form representation of a
chemical reaction. The chemical equation acts like a recipe, telling us which substances are the
reactants, the ingredients, which substances are the products, as well as the how much of each
substance is needed. The left side of the equation is the reactant. The right side is where the product is.
The arrow in the center of the equation separates both side from each other. To exactly know how
much of each substance is involved in the chemical reaction, as well as the relationship among them,
which will be used later on to find the limiting reagent (What Information Does a Chemical Equation
Tell Us?, 2014). We have to balance the chemical reaction in order to satisfy the Law of Conservation
of Mass. The law states that matter cannot be created or destroyed. However, it can change forms but
must be conserved. In chemistry, this basically means that in a chemical reaction​, the mass of the
products equals the mass of the reactants (Helmenstine​, 2017). ​It occurs when there is the equal
number of the different atoms of elements in the reactant side, comparing to the product side. For
instance, Me​4​N​+​I​-​ + I​2 →
​ Me​4​N​+​I​3​-​, this given equation is already balanced.

When conducting a chemical reaction, it is crucial to know the exact amount of reactants to
form a certain amount of product. Specific mole of reactants will produce specific mole of product.
This helps to maintain the amount of our limited resources. Furthermore, if there is an inadequate
amount of reactants, the process would cease precipitously. To avoid this, we have to primarily find
the limiting reagent. ​The limiting reagent is the reactant that is completely used up in a reaction, and
thus determines when the reaction stops (Shah, 2017). ​One way this could be done is by calculating
the product that would be produced from each reactant, that is to say, the one producing less product
is the limiting reagent. After the limiting reagent is discerned, the ​theoretical yield which is the
amount of product that could be produced in a perfect, idealized situation could then be found. The
product in gram formed by the limiting reagent is the theoretical yield. The percent yield can be
obtained when we divide the actual yield; which is the actual amount of product produced in the
chemical reaction, by theoretical yield and multiply them by 100.

In this experiment, we will be observing the chemical reaction between

Tetramethylammonium iodide (​Me​4​N​+​I​- ) ​and Iodine (​I​2) through
​ the process called crystallization.
The product of this chemical reaction is Tetramethylammonium triiodide in form of crystal.
Crystallization is the process of solidifying from solution (Karger, 2014). ​In Crystallization, a solid
substance is being dissolved in a liquid. By adding more and more of the solid, the solution will
eventually reaches the point beyond which no solid can longer dissolves. At this point the solution is
said to be saturated solution. ​However, by heating up the solution, more solid can be dissolved,
making the solution even more saturated and becomes supersaturated solution. This means that the
solution can only hold the solid when being placed under high temperature. So as the supersaturated
solution is left to cool down, the remaining solid that can no longer be dissolved comes out of the
solution and form crystal. The solution became less saturated afterward. In some case, the crystal
could be form through the process of precipitation as well. In precipitation, the product formed is
microcrystals, ​because the solubility was reduced too fast and crystals couldn't grow idiomorphic
(Difference between precipitation and crystallization, 2015).

The objective of this lab is to observe the formation of crystal through the synthesis of
Tetramethylammonium triiodide (​Me​4​N​+​I​3​-) ​and acknowledge the vitality of mass relationship; certain
amount of product would be produced only under certain circumstances. We also realize the
importance of determining the limiting reagent, excess reagent, calculating theoretical yield as well as
percentage yield in the real chemical reaction. The relationship between mole and mass of reactants,
products and how it affects the theoretical and actual yield.
Experiment
Material:
1. Tetramethylammonium Iodide ( N (CH 3 )4 I 3 )
2. Iodine ( I 2 )
3. 95% Ethanol ( C 2 H 5 OH )
4. Hexane ( C 6 H 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. Buchner funnel
9. Filter paper
10. Watch glass
11. Electronic Balance
12. Capped Vial

Procedure
1. Add 0.5 g of tetramethylammonium Iodide to a 50 mL beaker, and stir to break up clumps.
2. add 0.5 g of Iodine, and 12 mL of 95% Ethanol to that beaker.
3. In the fumehood, heat the beaker and stir until the substant completely dissolve
4. Heat at lower temperature
5. Remove the beaker from heat plate to room temperature for 10 minutes. The crystal should
form.
6. Place the beaker in the ice bath for 10 minutes to let the crystal grows more.
7. Pour the solution to the buchner funnel through the suction flask. The crystal is left at the
filter paper.
8. Wash the crystal twice with hexane to prevent contamination.
9. Dry the crystal overnight in the fumehood.
10. Collect the crystal
Results
The product of the experiment, tetramethylammonium triiodide ( N (CH 3 )4 I 3 ), is shown
below:

Figure1. Product after filtration Figure2. Product left overnight

The crystals of tetramethylammonium triiodide are countless small rod-shaped flakes. The color is
pure dark purple without any green from contamination. The crystals are shiny when they are placed
under sunlight. The product has an actual yield of 0.92 grams.
Discussion
1. Calculate the number of mole of each compound
mass
mole = molecular mass
0.5
mole N (CH 3 )4 I = 201.051 mol
mole N (CH 3 )4 I = 0.002486 mol

0.6
mole I 2 = 253.808 mol
mole I 2 = 0.002363 mol

2. Indicate the limiting reagent

0.5 g of tetramethyl iodine can produce 1.13 g of Tetramethyl Triodine, while 0.6 g of Iodine
consumed in the reaction can produce only 1.07 g. Therefore, Iodine is the limiting reagent in this
reaction.

3. express the amount of excess reagent remaining

0.002363 mol of Iodine, limiting reagent, is consumed in the reaction. The ratio of Iodine and
Tetramethyl Iodine is 1:1, therefore, 0.002363 of Tetramethyl Iodine is also consumed in the reaction.
mass
mole = molecular mass
mass
0.002363 = 201.051
0.475 g = mass
Therefore, there is 0.5 - 0.475 = 0.025 g of Tetramethyl Iodine left

4. Discuss the percent yield

actual yield
% yield = theoretical yield × 100
0.92
% yield = 1.07 × 100 = 86%
The actual yield of this reaction is 0.92 grams, if it is divided by 1.07, which is the theoretical yield,
and multiply by 100, the result will come out 86%, which means only 14% of yield is lost. This
percent yield is a really good number, as it is more than 80%.
5. Error
The product is yield more than 80%, therefore, there is no error in this experiment.
Conclusion
Based on the experiments, 0.6 grams or 0.0025 mole of tetramethyl iodine ( N (CH 3 )4 I ) and
0.5 grams or 0.0024 mole of Iodine ( I 2 ) produce 1.07 grams or 0.0024 mole of
tetramethylammonium triiodide ( N (CH 3 )4 I 3 ) crystal, where I 2 is the limiting reagent determining
the amount of the product. N (CH 3 )4 I is the excess reagent which 0.025 grams of it was not used.
The product’s crystals are small rod-shaped and has a color of pure dark purple. In this experiment,
0.92 grams N (CH 3 )4 I 3 is produced as an actual yield with the overall percent yield of 86%.

Suggestion
Some reaction may occur slowly, so, it takes time to make the reaction complete. If the
solution of Tetramethylammonium Triiodide is left in the ice bath longer, the percent yield might be
improved, or the catalyst might be added to shorten the time the reaction need to be completed.
The need to beware when weighing the reactant, the substances are needed to measured
accurately, when the solution is heated, it has to be measured in the exact amount of time, and when
the solution is filtered, it has to be poured through the buchner funnel carefully, so that there is no
crystal pass through the filter paper.

References
Studios, A. R. (n.d.). Chemical Reactions. Retrieved from
http://www.chem4kids.com/files/react_intro.htm​l
Help, F. H. (2014). What Information Does a Chemical Equation Tell Us? Retrieved from
https://schooltutoring.com/help/what-information-does-a-chemical-equation-tell-us/
Helmenstine, P. A. (n.d.). What Is the Law of Conservation of Mass? Retrieved from
https://www.thoughtco.com/definition-of-conservation-of-mass-law-604412
Limiting Reagent. (2017). Limiting Reagents. Retrieved from
https://chem.libretexts.org/Core/Inorganic_Chemistry/Chemical_Reactions/Limiting_Reagent
s
Karger, B. L. (2014). Exclusion and clathration. Retrieved from
https://www.britannica.com/science/separation-and-purification/Exclusion-and-clathration#re
f619631
Difference between precipitation and crystallisation. (n.d.). Retrieved from
https://chemistry.stackexchange.com/questions/39047/difference-between-precipitation-and-c
rystallisation
 Work log

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