SYNTHESIS OF

TETRAMETHYLAMMONIUM TRIIODIDE
Lab Report

BY
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 occur 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 equation can be calculated by using
the formula mass/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. 
Objectives
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
MATERIALS &
EQUIPMENTS

Tetramethylammonium Iodide
(0.5 g)

Iodine (0.6 g)

95% Ethanol (12 mL)

Hexane

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
 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
2. Indicate the limiting reagent and excess reagent

     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. The % yield

 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
Crystallization. (n.d.). Retrieved November 28, 2017, from
http://www.reciprocalnet.org/edumodules/crystallization/

Clark, J. (2012). MOLECULAR STRUCTURES. Retrieved

November 29, 2017, from
https://www.chemguide.co.uk/atoms/structures/molecula
r.html

PubChem. (2017). Tetramethylammonium iodide. Retrieved

December 03, 2017, from
https://pubchem.ncbi.nlm.nih.gov/compound/Tetramethylam
monium_iodide#section=2D-Structure

Chang, R., & Goldsby, K. (n.d.). Mass Relationships in

Chemical Reactions. In Chemistry (pp. 76-117).

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
Experimenting, Material, Objective,
Nont Calculation, Suggestion, Conclusion

Earn K. Experimenting, Discussion,

Calculation, Suggestion, Decoration

Experimenting, Objective, Abstract,

Van Introduction, Result, Analysis,
Conclusion

Namo Experimenting, Abstract, Flow chart

Chino Experimenting, Introduction, Reference

Fahlan Experimenting