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Lab Report

Synthesis of Tetramethylammonium pentaiodide

Date: 29th November 2017

Name Kanyaorn Ruetaijetjaroen 1104 5961221


Name Kanyarat Tirasirichai 1104 5961082
Name Nakamol Sansuktaweesub 1104 5961219
Name Nataphan Soontornworasate 1104 5961206
Name Nattawan Ekakkaravichit 1104 5961216
Name Thanthai Lapaviwat 1104 5961049
Abstract:
The 13 gram of Iodine, 12 mL of Ethanol, and 0.5 gram of Tetramethylammonium
Iodine are being heated up on the hot-plate and cooled down in the ice bath for 10
minutes each. After those processes finished, the dark green crystal started to form with
the weight of 1.25 gram. To summarize, the limiting reagent is Tetramethylammonium
Iodine and the overall percent yield from this experiment is 71.72%.

Objective:
The objective of this lab experiment is to understand the synthesis of
tetramethylammonium pentaiodide by combining tetramethylammonium and Iodine
together. In addition, this can be linked to the lesson in class, such as calculating of
molar mass and molecular weight of the atoms and molecules.

Introduction:
Every compound has unique chemical structure in which characterizes distinct
properties. Each chemical structure illustrates the composition and arrangement of a
compound(Drayer, 2006). Since the chemical structure is conducted for scientific
utilization and acknowledgement, balancing equation is significantly required in order to
calculate the product after chemical reaction is done, or to determine the amount of
each element that enables the reaction. A chemical equation is consist of elements on
two sides; the left side is for the reactants which starts up the reaction, and the product
is located on the right side(Khan Academy, 2017). As the reactants possess different
characteristics, there is a various range of duration which is taken up to be used by
each. The reactant that is used up first is known in terms of limiting reagent, the excess
reagent is the subsequence. According to Mikulecky and Hren (2017), “Chemists need
to know which reactant will run out first, because that information allows them to deduce
how much product and excess reagent they can expect.”. According to Khan
Academy(2017), “​The maximum amount of product that can be produced is called the
theoretical yield.” Some certain reactions react by the process of crystallization and
filtration in order to extract the product into the initial reactants. Crystallization is the
process when there is a massive amount of sugar dissolved in the boiling
supersaturated solution which allows the solute to dissolve in more than the solution’s
usual solubility, after the solution is cooled down, the crystal of the redundant sugar will
be formed(H. Douglas Goff, PhD., Julian Cooper, PhD., 2016). According to
Helmenstine, Ph.D.(2017), “Filtration is a process used to separate solids from liquids or
gases using a filter medium that allows the fluid to pass, but not the solid.”
In this experiment the Tetramethylammonium pentaiodide is the main product
that is observed from the chemical reaction between Tetramethylammonium iodide and
Iodine by the ethanol is acted as a solvent. The mixture is extracted by the process of
crystallization. The mixture is boiled and cooled down. The vacuum filtration is used in
order to collect crystal.
The purpose of the experiment is to apply knowledge from the lesson about such
as calculating of molar mass and molecular weight of the atoms and molecules.

Material:
1. Iodine(0.6g)
2. tetramethylammonium iodide
3. Beaker 50 mL beaker
4. Stirring rod
5. Hot-plate
6. Ice bath
7. Suction filtration
8. Hexanes
9. Funnel
10. Lab coat
11. Goggles
12. gloves

Procedure:
1. Add to a 50 mL beaker tetramethylammonium iodide ​(​0​.​5 g​). ​Use a stirring rod to
break up clumps of Me​4​N​+​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 iodide is dissolved​.
4. Heat at a low temperature to prevent premature crystallization​.
5. Remove from the heat and allow the beaker to cool down 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 about 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 crystals 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 name, the name of the
compound and the date to the lab instructor​.
Result of the experiment:

As you can see from the picture, it is a picture of 1.25g Tetramethylammonium


Pentaiodide which is the crystal that formed by the combination of
Tetramethylammonium Iodide, iodine, and also ethanol. This product is almost like the
colored powder but not totally powder though as there is still some lumps all over. The
color is almost black but it contains a little green in it.

Reactants

Tetramethylammonium Iodide 0.5 gram

Iodine 1.3 gram

Product

Tetramethylammonium Pentaiodide 1.25 gram


Calculation:
+​ -​
Equation​: (CH​3​)​4 N​
​ I​ + 2I​2​ (CH​3​)​4​N​+​I​5​-
0.5g 1.3g

Find mol​:
+​ - ​
1.(CH​3​)​4 N​

+​ -​
I​ : 0.5 g x 1 g x 1 mol (CH​3​)​4 N​
​ I​ / ​201g(CH​3​)​4 N​

+​ -
I​

= 2.488 x 10​-3​ mol (CH​3​)​4 ​N​+​I​-

2. I​2​ = 1.3g x 1 mol I​2​ ​/​ 254g(I​2​)

= 5.118 x 10​-3 mol I​2

Find limiting reagent​:

(CH​3​)​4 N​

+​ -​
I​ : 2.488 x 10​-3​ mol (CH​3​)​4 N​
​ I​ x 1 mol (CH​3​)​4​N​+​I​5​-​ ​/​ 1 mol (CH​3​)​4 N​
+​ -​

+​ -
I​

= 2.488 x 10​-3 ​ mol (CH​3​)​4​N​+​I​5​-

I​2​ : 5.118 x 10​-3​ mol I​2​ x 1 mol (CH​3​)​4​N​+​I​5​-​ ​/ ​2 mol I​2

= 2.559 x 10​-3​ mol (CH​3​)​4​N​+​I​5​-

(CH​3​)​4 N​
​ I​ is a limiting reagent so (CH​3​)​4​N​+​I​5​-​ = 2.488 x 10​-3 ​ mol
+​ -​

Tetramethylammonium pentaiodide mass​ = 2.488 x 10​-3 ​ mol (CH​3​)​4​N​+​I​5​-

Actual yield​ = 1.25 gram

Theoretical yield​ = 1.76 gram

Percent yield​ = 71.02 %


Result of the calculation

Molar Mass

Tetramethylammonium Iodide 2.488 x 10​-3​ mol

Iodine 2.559 x 10​-3​ mol

Tetramethylammonium Pentaiodide 2.488 x 10​-3​ mol

Yield

Actual yield 1.25 gram

Theoretical yield 1.76 gram

Percent yield 71.02 %

In order to calculate the molar mass, it can be determined from the mass we
used or the mass we got. Then convert the exact mass of the molecules compare to
mole. Basically, the yield that we got from the measurement was 1.81 gram including
the mass of the paper. So that we need to subtract the mass of the paper out of the
mass of product. The equation is mass product - mass paper, so it was 1.81-0.56 = 1.25
gram.

Discussion:
The synthesis of Tetramethylammonium pentaiodide experiment used two
reactants to form the products which is the Tetramethylammonium Pentaiodide. The
reactants in the experiment included Tetramethylammonium Iodide and Iodine.
+​ -
Moreover, the chemical equation of this synthesis is (CH​3​)​4 N​ ​ I​ + 2I​2
+​ - +​ -
(CH​3​)​4​N​ I​5​ . First, the (CH​3​)​4 N​
​ I​ is the Tetramethylammonium Iodide and I​2
represented Iodine. In this experiment, we used 0.5 gram of Tetramethylammonium
Iodide and 1.3 gram of iodine which both of them were equal to 2.488 x 10​-3 mol (CH​3​)​4
N​+​I​- ​and 5.118 x 10​-3 ​mol I​2. Whereas
​ the product which is the Tetramethylammonium
pentaiodide, weighed 1.25 gram or 2.488 x 10​-3​ mol.
According to the stoichiometry, there is an exact amount of the reactant that will
be used in order to create one amount of product in a fixed ratio in each chemical
reaction. The limiting reagent will be used to compare the ratio of the product so that we
can figure out the theoretical yield of the experiment. In addition, the limiting reagent is
the reactant that will be used up first in the chemical reaction (Khan Academy, 2017).
The least one will be considered as the limiting reagent. In this case was the
Tetramethylammonium Iodide which is 2.488 x 10​-3 mol. This amount of mol can be
used to find the theoretical yield or the expected mass of the product. From the
calculation, we expect to have 1.76g for Tetramethylammonium Iodide and lastly, we
get the same as we expect.
Our actual yield is same as expectation. As a result, we get the accurate answer
same as our expectation, so there is no any errors.

Conclusion:
In conclusion, tetramethylammonium iodide and iodine were mixed together
adding ethanol and being heated in which resulted in dark green powder. Therefore, the
product in terms of tetramethylammonium pentaiodide was 1.25 gram, 2.488 x 10​-3 mol,
and 71.02% yield. Tetramethylammonium iodide is the limiting reagent of the reaction
while iodine is remain excess in the solution.

Reference:
- Drayer D., (2006). What does a chemical formula tell?. Retrieved from
https://socratic.org/questions/what-does-a-chemical-formula-tell

- Khan Academy, (2017). Balancing chemical equations. Retrieved from


https://www.khanacademy.org/science/chemistry/chemical-reactions-stoichiome/balanci
ng-chemical-equations/v/balancing-chemical-equations-introduction

- Mikulecky P. J. and Hren C., (2017). Calculate Limiting Reagents, Excess Reagents,
and Products in Chemical Reaction. Retrieved from
http://www.dummies.com/education/science/chemistry/calculate-limiting-reagents-exces
s-reagents-and-products-in-chemical-reactions/

- Goff H. D., PhD., Cooper J., PhD., (2016). Beyond Sweetness: The Functional Roles of
Sugar in Foods and the Challenges in Replacing/Reducing It.
http://www.sugar.ca/SUGAR/media/Sugar-Main/PDFs/Carbohydrate-News-Sugar-Functi
ons-Beyond-Sweetness.pdf

- Helmenstine A. M., PhD., (2017). Filtration Definition and Processes (Chemistry).


Retrieved from ​https://www.thoughtco.com/filtration-definition-4144961

- Khan Academy, (2017). Limiting Reagents and Percent Yield. Retrieved from
https://www.khanacademy.org/science/chemistry/chemical-reactions-stoichiome/limiting-
reagent-stoichiometry/a/limiting-reagents-and-percent-yield
WORKLOG:

NAME JOB/ROLE

Kanyarat Cover page + Abstract + Conclusion

Nakamol Introduction + References

Nataphan Table conclusion + Conclusion

Nattawan Objective + Discussion + Front page

Thanthai Introduction + Research + Calculation

Kanyaorn Result table + Discussion + Calculation

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