7 December 2017

Synthesis of Tetramethylammonium Pentaiodide

Krittin Tansida
Tanrak Phohom
Thanyarat Lohapark
Panicha Vongthoytong
Natthapat Chatthanayongphakdi
Wutthipong Sarawutikai

Abstract
This experiment was conducted to study the chemical reaction between
Tetramethylammonium Iodide and iodide, to perform crystallization, and to determine the limiting
reagent and % yield of the synthesis of tetramethylammonium pentaiodide. The
tetramethylammonium pentaiodide was performed under the process of heating, filtration, and
crystallization using 1.31 grams of Iodine and 0.50 grams of Tetramethylammonium Iodide as
reactants. As the result, we got tetramethylammonium pentaiodide of 1.71 grams of olive-green color
and percent yield of 97.16%.

Objective
The purpose of this Lab is to study the chemical reaction between Tetramethylammonium
Iodide and Iodine, to synthesis tetramethylammonium pentaiodide, to perform crystallization, and to
determine limiting reagent and % yield of tetramethylammonium pentaiodide.

Introduction
Chemical reaction is a change in chemical by which chemicals interact to form a new
substance under the process of transforming the reactant, an initial substance; into the product, final
substance (Helmenstine, 2017). It’s mostly represented by a chemical equation which can be written
in form of chemical formula to displays the formation of a product from its element. Moreover, the
equation must be balance on both sides by making used of the coefficient to balance in order that we
can make use of the equation to calculate in further calculation including: mole, limiting reagent, and
percent yield. Mole refers to the fundamental Standard International Unit of measuring the material
quantity (Rouse, 2005). Besides, it is use to calculate the limiting reagent, ​the reactant that determines
how much the products are being produced, and theoretical yield, the maximum amount of product
that can be produced (Khan Academy, n.d.).
Crystallization is the process of transforming gas or liquid substance into solid substance by
solidification of atoms into crystal ​(Helmenstine, 2017)​. During the process, the reactants will be
heated, cool down and filtrate using ​vacuum filtration.
According to this experiment, the reactant are ​Tetramethylammonium Iodide and Iodide and
the product is tetramethylammonium pentaiodide, or can be written as C ​ ​4​H​12​N​+·​ I​5-​ in a chemical
formula.​ We use limiting reagent and % yield for calculating the actual amount of the product and the
amount of percent error in the experiment.
Material

1. 0.5 g of Tetramethylammonium iodide

2. 1.31 g of Iodine
3. 12 mL of 95% ethanol solution
4. 50 mLbeaker
5. stirring rod
6. ice bath
7. hot plate
8. vacuum filtration
9. hexanes
10. petri dish

Method

1. Add 0.5g of Tetramethylammonium iodide into 50 mL beaker.

2. Use a stirring rod to break up clumps of tetramethylammonium iodide.
3. Add 1.3 g of iodine and 12 mL of 95% ethanol into the 50 mL beaker.
4. In a fumehood, heat the solution gently, with stirring, on a hot plate for about 10 minutes until
tetramethylammonium iodide has dissolved.
5. After 10 mins, start to heat the solution at low temperature to prevent premature
crystallisation.
6. Remove the beaker from heat, allow the beaker to cool down the temperature, and don’t
disturb it (because it can cause the crystal to not be formed)
7. Once at room temperature, place the beaker in ice for about 10 minutes. While it is being
cooled down, set up the apparatus filtration.
8. Using the vacuum filtration, collect crystals and wash them with hexanes.
9. Air-dry the product and weigh.
10. Hand in the sample stored, in a petri dish

Results From Experiment

Reactant

Tetramethylammonium iodide 0.50g.

Iodine 1.31g.

Product

Tetramethylammonium pentaiodide 1.71 g

We use 0.50g. of Tetramethylammonium iodide and 1.31g. of Iodine to be the reactant. The final mass
of Tetramethylammonium pentaiodide is 1.71g.
 Molar Mass

Tetramethylammonium iodide 2.49x10​-3

Iodine 5.16x10​-3

Tetramethylammonium pentaiodide 2.49x10​-3

Yield

Actual yield 1.71g.

Theoretical yield 1.76g.

Percent yield 97.16%

According to the result, we got an actual yield 1.71g and the theoretical yield 1.76g. After we
calculated the percent yield the results is 97.16%. The result came out with the olive-green powder of
the substance that has unfixed shape and doesn’t have the smell.

As you see in the picture above, the product is tetramethylammonium iodide

which has the olive-green powder of the substance that has unfixed shape
and doesn’t have the smell.

Calculations
Chemical equation: (CH​3​)​4​N​+​I​-​ + 2I​2​ -> (CH​3​)​4​N​+​I​5
Molecular weight of tetramethylammonium iodide
= 4(12.0107)+12(1.00794)+14.0067+126.90447 = 201.04925 amu = 201.05 amu
Molecular weight of tetramethylammonium pentaiodide
=4(12.0107)+12(1.00794)+14.0067+5(126.90447) = 708.66713 amu = 708.67 amu
Molecular weight of iodine​ = 2(126.90447) = 253.80894 amu = 253.81 amu
Mass of tetramethylammonium pentaiodide from tetramethylammonium iodide
0.50 g of (CH​3​)​4​N​+​I​-​ x (1 mol (CH​3​)​4​N​+​I​-​ / 201.05 g of (CH​3​)​4​N​+​I​-​) x (1 mol (CH​3​)​4​N​+​I​5​ / 1 mol
(CH​3​)​4​N​+​I​-​) x (708.67 g of (CH​3​)​4​N​+​I​5​ / 1 mol (CH​3​)​4​N​+​I​5​) = 1.76 g of (CH​3​)​4​N​+​I​5​ -> ​produce less
Mass of tetramethylammonium pentaiodide from iodine
1.31 g of I​2​ x (1 mol I​2​ / 253.81 g of I​2​) x (1 mol (CH​3​)​4​N​+​I​5​ / 2 mol I​2​) x (708.67 g of (CH​3​)​4​N​+​I​5​ / 1
mol (CH​3​)​4​N​+​I​5​) = 1.83 g of (CH​3​)​4​N​+​I​5

Tetramethylammonium iodide is limiting reagent.

Actual yield = 1.71 g of (CH​3​)​4​N​+​I​5

Theoretical yield = 1.76 g of (CH​3​)​4​N​+​I​5

Percent yield = 1.71g of (CH​3​)​4​N​+​I​5​ /1.76 g of (CH​3​)​4​N​+​I​5 ​ x 100% = 97.16%

Discussion

Pre-lab discussion
The objective of this Lab is to study the chemical reaction between Tetramethylammonium
Iodide and Iodine, to synthesis tetramethylammonium pentaiodide, to perform crystallization, and to
determine limiting reagent and % yield of tetramethylammonium pentaiodide. The background
information that we need to know are molar mass, limiting reagent, difference between theoretical and
actual yield, solution to find percent yield, and crystallization.
Temperature affects the crystallization of tetramethylammonium pentaiodide. According to
Etter(n.d.), temperature that is used in boiling need to be high to make the solution mix together.
The step that we have the most concerned in this experiment is filtration because hexane is
used for washing the crystal, and if you wash it not clean, then there will be something contaminate in
the crystal.

Post-lab discussion
From the experiment, 0.50 g of tetramethylammonium iodide and 1.31 g of iodine are
reactants that are used for producing tetramethylammonium pentaiodide. After the experiment, the
product is measured, and it weigh 1.71 g. Also, molar mass of each compounds are measured which
tetramethylammonium iodide, iodine and tetramethylammonium pentaiodide are 2.49x10​-3​, 5.16x10​-3​,
and 2.49x10​-3​ mol, respectively. The product came out with the olive-green powder of the substance
that has unfixed shape and doesn’t have the smell.
In addition, stoichiometry, which is the topic that we are studying, is related to this
experiment. The limiting reagent is a reactant that produce the product at first. The limiting reagent
can be found by calculating the mass of each reactants that can produce the product and compare
which one is the least, the one that is the least will be limiting reagent. As the calculation,
tetramethylammonium iodide can produce 2.49x10​-3​ mol of (CH​3​)​4​N​+​I​5​, and iodide can produce
5.16x10​-3​ mol of (CH​3​)​4​N​+​I​5​, so the limiting reagent is tetramethylammonium iodide.
Moreover, as you see in the result, the actual yield and theoretical yield aren’t the same
amount. The actual yield is less than the theoretical yield. This is caused by other chemical reaction
react with it make it become not accurate. In the experiment, The actual yield that we’ve got from the
experiment is 1.71 g of (CH​3​)​4​N​+​I​5​, and the theoretical yield has 1.76 g of (CH​3​)​4​N​+​I​5​. After we
calculate the percent yield, it is 97.16%, so it precise but not accurate.

Conclusion
In conclusion, the final product that came out was 1.71 grams, but the theoretical yield is 1.76.
Therefore, the percent yield is 97.16% ((1.71/1.76) x 100) which is pretty much accurate to the actual
yield.

References
Helmenstein, M. A. (2017, April 25). ​Chemical Reaction Definition and Examples. ​Retrieved 2017,
December 6 from ​https://www.thoughtco.com/chemical-reaction-definition-606755

Rouse, M. (2005, September). ​Mole. ​Retrieved 2017, December 6 from

http://whatis.techtarget.com/definition/mole

Khan Academy. (n.d.) ​Limiting Reagent and Percent Yield. ​Chemical Reaction and Stoichiometry
Retrieved 2017, December 6 from
https://www.khanacademy.org/science/chemistry/chemical-reactions-stoichiome/limiting-reagent-stoi
chiometry/a/limiting-reagents-and-percent-yield

Etter C. M., (n.d.) ​Crystallization.​ Retrieved 2017, December 6 from

http://www.reciprocalnet.org/edumodules/crystallization/