Lab Report

Synthesis of Tetramethylammonium Pentaiodide

Jadejirat Boonprasit 5961215

Ramita Chalearmchutidath 5961017

Thanakorn Maleesut 5961166

Ingkarat Wachapatthana 5961118

Accelerated chemistry 1105

Ms. Patraporn Sanguansat
Mahidol University International Demonstration School
Semester 1 Academic year 2017-2018
 Introduction
Tetramethylammonium (Me4N+) is a cation composing of four methyl groups
attached to a nitrogen atom. “Iodine is a black, shiny, crystalline solid. When heated,
iodine sublimes to form a purple vapour.”(Royal Society of Chemistry, 2017). It has an
atomic number of 53, stated at the 5th period on the periodic table. It is considered to be
in the halogen group or group 7A elements. Mole is a standard international unit (SI) for
the measurement of amount of particles in a substance. According to LibreTexts (n.d.),
the number of moles in a can be determined using the atomic mass of an element,
which can be found on the periodic table. One mole is defined by Avogardo’s
number/constant at the approximate of 6.022 x 1023 atoms/molecules. Mole calculation
are applied in chemical reactions to find other parts and variables in the reaction
including the ratio and mass of certain reactants or products in the reaction. It is also
used to find the limiting and excess reagent of the reaction. In a chemical reaction, the
limiting reagent is the reactant that determines how much of the products are made
(Khan Academy, n.d.). Apart from the limiting reagent, others are considered to be
excess reagent since they have leftovers after the reaction is completed and the limiting
reagent is completely used up. The maximum amount of product that can be produced
is called the theoretical yield. However, scientists cannot obtain the maximum yields
from the reaction due to some possible errors during the process. “Amounts of products
calculated from the complete reaction of the limiting reagent is called theoretical yields,
whereas the amount actually produced of a product is the actual yield.”(UWaterloo,
n.d.). The rate between the actual yield and the theoretical yield is called the percentage
yield, obviously shown in the form of percentage.
In this experiment, the attempt to synthesize Tetramethylammonium Pentaiodide
is carried out. Tetramethylammonium and Iodine are the reactants of this chemical
reaction. Tetramethylammonium Pentaiodide (Me4N+I5), is synthesized by mixing
Tetramethylammonium iodide (Me4N+I- ) and Iodine (I2) together. Crystallisation is used
to separate out a solid substance from a liquid solution. To perform this method, certain
conditions must be met at each step within this process. The solution must be heated
up to allow the rearrangement of ions and atoms and cooled down to form a crystal.
Hexane, an organic colorless liquid, is used to clean crystals from the solution after
undergoing filtration as a final finishing to have a clear and pure result. It is widely used
since it is cheap and are highly unreactive which are considered to be safe to use,
under provision of experts.

Objective
1.To study crystallization.
2. To study the mole calculation.
3. To study the limiting reagent identification.
4. To study the yield of experiment work calculation.

Procedure
1. Add to a 50mL beaker tetramethylammonium iodide(0.5 g). Use a stirring rod to
break up clumps of Me4N+I-
2. Add iodine(1.3 g) and 95% ethanol (12 mL).
3. In a fume hood, gently heat the beaker, with stirring, on a hot-plate for about 10
minutes until tetramethylammonium has dissolved.
4. Heat at a low temperature to prevent premature crystallization.
5. Remove from the heat and allow the beaker to cool undisturbed (Agitating the
solution can cause smaller crystals to form which are more difficult to isolate and
tend to occlude impurities).
6. The crystals should form during this time.
7. Once at room temperature, further cooling can be achieved by placing the beaker
in an ice bath for 10 minutes, only put the solution on ice if necessary. During this
time, set up the apparatus for suction filtration.
8. Using vacuum filtration, collect the crystal and wash them with hexanes (5 mL
portions until filtrate dropping from funnel is colorless, max. 5 washings).
9. Air-dry the product with weigh.
10. Hand in a sample, in a capped vial, labelled with your names, the name of the
compound and the date to the lab instructor.

Result

Me4N+I- + I2 → Me4N+I5
1. Balance the equation. If the equation has already balanced, then move to the
next step.
Me4N+I- + 2I2 → Me4N+I5

2. Find the limiting reagent because it is the reactant that is used up first in the
reaction, which is crucial for further calculations.

3. In order to calculate the limiting reactant, we need to know the molecular weight
first.

Mw Me4N+I- = 201.04 MwI2 = 253.8

4. Use the mole ratio to calculate the limiting reagent

𝑀𝑎𝑠𝑠 𝑀𝑎𝑠𝑠
(𝑀𝑜𝑙𝑒𝑐𝑢𝑙𝑎𝑟 𝑊𝑒𝑖𝑔ℎ𝑡 ÷ 𝐶𝑜𝑒𝑓𝑓𝑖𝑐𝑖𝑒𝑛𝑡 = 𝑀𝑜𝑙𝑒𝑐𝑢𝑙𝑎𝑟 𝑊𝑒𝑖𝑔ℎ𝑡 × 𝐶𝑜𝑒𝑓𝑓𝑖𝑐𝑖𝑒𝑛𝑡)

● Me4N+I

0.5 g ÷1 = 0.00248707

201.04

Me4N+I = Limiting Reagent

● 2I2

1.3 g ÷2 = 0.00256107

253.8

2I2 = Excess Reagent

5. After getting the limiting reagent, use the limiting to compare the mole ratio with
the product for calculating the amount of the product formed.
 𝑀𝑎𝑠𝑠 𝑀𝑎𝑠𝑠
Formula (𝑀𝑜𝑙𝑒𝑐𝑢𝑙𝑎𝑟 𝑊𝑒𝑖𝑔ℎ𝑡 ÷ 𝐶𝑜𝑒𝑓𝑓𝑖𝑐𝑖𝑒𝑛𝑡 = 𝑀𝑜𝑙𝑒𝑐𝑢𝑙𝑎𝑟 𝑊𝑒𝑖𝑔ℎ𝑡 × 𝐶𝑜𝑒𝑓𝑓𝑖𝑐𝑖𝑒𝑛𝑡)

0.5 g ÷1 = mass ÷1

201.04 708.8

Mass of Me4N+I- = 1.763 g (theoretical yield)

𝐴𝑐𝑡𝑢𝑎𝑙 𝑌𝑖𝑒𝑙𝑑
6. Finding the percent yield ( × 100)
𝑇ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙
Actual yield (mass of product) = 1.07g

Theoretical yield = 1.7633263 g

1.07 x 100 = 60.6807713%

1.7633263

Thus, our percent yield is 60.68%

The mass and percent yields of the product, Tetramethylammonium Pentaiodide

Mass of actual Tetramethylammonium 1.07 g
Pentaiodide (Me4N+I5)

Mass of theoretical 1.7633263 g

Tetramethylammonium Pentaiodide
(Me4N+I5)

Percent Yield 60.68%

Observations

After undergoing the experiment, the result we got was a pure solid crystal with a green
color without any contamination, considered to be Tetramethylammonium pentaiodide.
The shapes of the crystal were in small flakes which glitter when placed under a source
of light. Although there are some parts where the crystals did not form yet. These parts
came in as powders of black and dark green pigments and do not reflect off the light
from the sun.

Figure1 : Product under the sunlight

Discussion

For the summary and overview of this experiment, using the given substances
including tetramethylammonium iodide(0.5 g), iodine(1.3 g), and 95% ethanol(12 mL),
tetramethylammonium pentaiodide is made. After breaking down the clumps using the
stirring rods, we proceed to heat the beaker containing the solution in the fume hood for
about 5 minutes. After that we take it out to cool down at room temperature.
Consequently, the beaker is placed in the ice for further cooling for another 5 minutes.
Finally, we used vacuum filtration to separate the crystal from the solution, and washed
them with hexanes, henceforth air drying the product before weighing it. After
completing the experiment, there were some errors we might make during the
experiment, with or without realizing. First, we might contaminate the substance while
transferring the substances from one container to another. In the same way, the beaker
may not be properly placed in the ice. The beaker maybe accidentally lifted during the
process which could alter the formation of crystal. Furthermore, when the solution is
heated, after a period of time, there was a mistook of time, so the method is stopped
late by about half a minute or less which can possibly affect the result. For the things
we’ve learned from this experiment, we are quite sure that the most obvious ones are
“teamwork” and “time management” because this lab gives us such limited time that
every members cannot stay on one task at a time or we would run out of time, we have
to assign different jobs for the people in the group in order to complete the lab fluently
and quickly.

Conclusion
In conclusion, we got 1.763 g of tetramethylammonium pentaiodide as the
product, while the percent yield is 60.6807713%. Tetramethylammonium iodide is the
limiting reagent and iodine is the excess reagent, 1 mole of Tetramethylammonium
iodide react with 2 moles of Iodine could produce 1 mole of tetramethylammonium
pentaiodide. Small green crystals are formed in the final product. On the contrary, there
are still some parts of the product that did not form crystals yet, due to the limited time
for heating up and cooling down process of the solution.

Suggestion

During the experiment, there are many problems that take place in our group. The first
suggestion is that our group should be more delicate and careful. After the solution was
mixed well, it accidentally spill off because one of our group member was careless. In
consequences, time was also taken in cleaning up the mess and setting up the solution
again which also resulting have lesser time for other methods. The second suggestion
is that our group have to be better at managing the time. Actually we should heat our
solution for 10 minutes but we did not manage the time well, so we have only 5 minutes
for heating the solution. As a result, the percent yield of the product came out quite low.
The third suggestion is that we need more communication. During the experiment, we
did not communicate to each other well so each member did not know what exactly they
need to do. Consequences, we could not work effectively as each member did not know
what they have to do.
Figure 1: Only 5 minutes for heating Figure 2: Accidentally spill the solution

Reference
- Pubchem. (2017). Tetramethylammonium iodide. retrieved from
https://pubchem.ncbi.nlm.nih.gov/compound/Tetramethylammonium_iodide#section=To
p
- Khan Academy. (n.d.). Limiting reagent and percent yield. retrieved from
https://www.khanacademy.org/science/chemistry/chemical-reactions-stoichiome/limiting-
reagent-stoichiometry/a/limiting-reagents-and-percent-yield
- Britannica. (2016). retrieved from https://www.britannica.com/science/separation-and-
purification/Exclusion-and-clathration#ref619631
- Sciencedirect. (2008). Hexane. retrieved from
http://www.sciencedirect.com/topics/neuroscience/hexane
- Merck. (2015). Ethanol. retrieved from
https://www.sigmaaldrich.com/catalog/product/sial/652261?lang=en&region=TH
- Royal Society of Chemistry. (2017). Iodine. retrieved from http://www.rsc.org/periodic-
table/element/53/iodine
- LibreTexts. (n.d.). Mole unit. retrieved from
https://chem.libretexts.org/Core/Physical_and_Theoretical_Chemistry/Atomic_Theory/Th
e_Mole_and_Avogadro%27s_Constant
 - UWaterloo. (n.d.). Theoretical and actual yield. retrieved from
http://www.science.uwaterloo.ca/~cchieh/cact/c120/yields.html

Abstract

In this experiment, we were experimenting on the synthesis of

tetramethylammonium pentaiodide. Follow the steps in flowchart. First, We placed 0.5 g
of Tetramethylammonium iodide and 1.3 g of Iodine and 12 ml of 95% Ethanol as
reactant and mix it together. After mixing the substances together, the solution is heated
up by a hot plate under a fume hood for 5 minutes. Then it is left to cool down at room
temperature for 5 more minutes. For these recent two steps, we supposed to did both of
it for 10 minutes according to the flowchart but we didn’t be able to as we spilled the
solution. As a result, we need to finish each step at only 5 minutes due to the
insufficient of time for the experiment. At the end, the beaker containing the solution is
taken into an ice bath for catalyzing the process which the crystals are formed. After
getting cooled down, the solution is vacuum filtrated, leaving the crystal on the filtration
paper which we have to be aware of contamination. This is because in the filtration
process, we want pure substance. Finally, before weighing the mass of the crystal,
hexane is used to wash the solution. The result was successfully formed, we eventually
got a polished greenish crystal. Although some parts of the results did not form crystals,
due to the limited time for each of the steps. From our calculation, we found out that
Me4N+I- is the limiting reagent of this chemical reaction, while I2 is the excess reagent.
The mass of our product is 1.763 g. The percent yield was 60.6807713%. If the
experiment was to conduct again, the time for heating the solution, cooling the solution,
and weighing the reactants and product should be more accurate.

Work Log

Peng Experiment, Suggestion

Pru Result, Conclusion

Ing Introduction, Discussion, Reference

Oil Abstract, Objective