Lab Report

Synthesis of Tetramethylammonium Pentaiodide

By
Chayanin Sakulboonthanom (China) 5961059
Jiratchaya Nimitpanya(Unging) 5961071
Natthida Amnuay-ngenrtra (Mint) 5961173
Nuttaya Techapermphol (View) 5961107
Tawisa Atipanan (Ta) 5961060
1106

Chemistry
Ms. Sorasaree Tongsiengsom
Mahidol University International Demonstration School
Quarter 2 Semester 1
Academic Year 2017-2018
Abstract:
The synthesis of tetramethylammonium pentaiodide uses tetramethylammonium
iodide (0.5 grams) mix with iodine (1.3 grams) and ethanol (12 mL). Then these materials
are heated and cooled down. When it cools down, it will form crystals. Next, vacuum filtration
is used to collect the crystals. During the procedure, the crystals are washed by hexanes.
After that, wait for the product to dry in order for the crystal to purify. Finally, we weigh out
the product, in which our group’s final product weigh 1.12 grams. At last, we calculate the
percent yield of the experiment. Therefore, our experiment is 63% yield.

Object:
The purpose of this lab experiment is to study about chemical reaction from
synthesizing tetramethylammonium pentaiodide and for students will have an opportunity to
perform crystallization. Moreover, students would be able to determine the limiting reagent,
excess reagent, and calculate the percent yield from the performed experiment as learned in
class.
Introduction:
In order to understand all of the chemical reactions, the basic thing that needs to be
understand is chemical bonding. Chemical bonding occurs to make the atom stable;
therefore, electron, especially the valence electron, is the main focus in chemical bonding
(Libretexts, 2014). Chemical bonding can be divided into two types; ionic bond and covalent
bond. Ionic bond is when the atom loses or gains electron from another atom. On the other
hand, covalent bond is when two atoms share its electron. In which these bonding must
follow the octet rule which states that the atom is stable when the valence electron has eight
electrons except Hydrogen which has only two (Papiewski, n.d.). As a result, chemical
bonding makes atoms react with each other and create a new substance which the process
is called chemical reaction. As each chemical reaction uses certain type and amount of
substance, this leads to the difference of chemical equation. Hence, it is important to
balance the equation; making the amount of reactants and amount of product equal, which
this can be done by changing the coefficient in front of each reactant or product. We have to
consider the equivalent of coefficient from the balanced equation to calculate for theoretical
yield or the maximum amount of product that can be produced from a certain amount of
reagents. And according to the experiment, the chemical formula is ​(CH​3​)​4​N​+​I​- + 2I​2 ->
(CH​3​)​4​N​+​I​5​- in which (CH​3​)​4​N​+​I​- ​is tetramethylammonium iodide, ​I​2 is
​ iodine, and (CH​3​)​4​N​+​I​5​- ​is
Tetramethylammonium Pentaiodide. Then we will use the theoretical yield and the actual
yield; actual amount that is produced from the experiment, to calculate the percent yield;
actual yield / theoretical yield x 100 (Ck12 Science, 2013). And according to the experiment,
crystallization and filtration is used. Firstly, crystallization is a method used to separate a
purified solid substance(crystals) from the liquid solution which the crystals came from the
solute in a supersaturated solution, a solution that has more undissolved solute than the
heated saturated solution since the saturated solution cannot dissolve solute anymore if it is
not heated. Therefore, when the supersaturated solution cools down, the undissolved solute
will form purified crystals (Libretexts, 2014). Then, after the crystallization procedure, purified
crystals and the solution are separated by filtration. Filtration. In this case, vacuum filtration
is used because it is fast which it ​reduced pressure in the flask then air and liquid substance
will be sucked in and solid substance will be filter by the filter paper (Libretexts, 2017).
Material and Method:
Materials
- 0.5 g tetramethylammonium iodide
- 1.3 g iodine
- 12 mL 95% ethanol
- Weighing paper
- Weighing balance
- 50 mL beaker
- 50 mL graduated cylinder
- Stirring rod
- Magnetic stirrer
- Hot plate
- Ice bath
- Timer
- Filter paper
- Filtration Flask
- Hexane
- Petri dish

Procedure
1. Add to a 50 mL 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 iodide was dissolved.
4. Heat at a low temperature to prevent premature crystallization.
5. Remove from the heat and allow the beaker to cool down undisturbed.
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
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.
Results:

Reactant Product

Chemical Formula (CH​3​)​4​N​+​I​- 2 I​2 (CH​3​)​4​N​+​I​5​-

Amount (grams) 0.5 g 1.3 g 1.12 g

Amount (mole) 0.00249 mol 0.00512 mol 0.00158 mol

Act as Limiting reagent Excess reagent

Appearance

dark green powdery substance

Theoretical yield 1.76 g

Actual yield 1.12 g

Percent yield 63%

Calculation ​:
Synthesis of tetramethylammonium pentaiodide
(CH​3​)​4​N​+​I​-​ + 2I​2​ -> (CH​3​)​4​N​+​I​5​-

Molecular weight :
1. (CH​3​)​4​N​+​I​-​ : 4 ( 12 + 3 ) + 14 + 127 = 201 g
2. I​2​ :​ 127 x 2 = 254 g
3. (CH​3​)​4​N​+​I​-​5​ : 4 ( 12 + 3 ) + 14 + 5 ( 127 ) = 709 g

Mole
1. (CH​3​)​4​N​+​I​- ​ : 0.5g of (CH​3​)​4​N​+​I​-​ x 1
​ mol of (CH​3​)​4​N​+​I​-​ = 0.0249 mol
201 g
2. I​2 :​ 1.3g of I​2 x​ ​1 mol of I​2​ = 0.00512 mol
254 g of I​2
3. (CH​3​)​4​N​+​I​-​5​ : 1.12g of (CH​3​)​4​N​+​I​-​5​ x ​1 mol of (CH​3​)​4​N​+​I​-​5​ ​= 1.158 mol
709 g of(CH​3​)​4​N​+​I​-​5
(CH​3​)​4​N​+​I​-​ = 0.5 g x ​1 mol (CH​3​)​4​N​+​I​-​ ​x ​1 mol (CH​3​)​4​N​+​I​5​- ​ x ​709 g (CH​3​)​4​N​+​I​5​-
201 g (CH​3​)​4​N​+​I​-​ 1 mol (CH​3​)​4​N​+​I​-​ 1 mol (CH​3​)​4​N​+​I​5​-
= 1.76 g (CH​3​)​4​N​+​I​5​- ​ (limiting reagent) -> theoretical yield

I​2​ = 1.3 g x ​1 mol I​2​ x 1 mol (CH​3​)​4​N​+​I​-​5​ x ​709 g (CH​3​)​4​N​+​I​5​-

254 g I​2 ​ 2 mol I​2 1 mol (CH​3​)​4​N​+​I​5​-
= 1.814 g (CH​3​)​4​N​+​I​5​-​ (excess reagent)

% yield​ = ​ actual yield ​ x 100

theoretical yield
= ​1.12​ x 100
1.76
= 63% yield
Mole​ = 1.12g of (CH​3​)​4​N​+​I​-​ x 1
​ mol of (CH​3​)​4​N​+​I​5​-​ = 0.00158 mol
709 g

Discussion:
For this experiment, the objective of this lab is to study about chemical reaction from
synthesizing tetramethylammonium pentaiodide. However, we need to have the basic
knowledgement of chemical bonding for instance Chemical bonding can be divided into two
types; ionic bond and covalent bond. Ionic bond is when the atom loses or gains electron
from another atom. In this experiment, we need to aware about temperature and disturbance
system during crystallization because It can affect the result of chemical bonding in different
way. The result that we found is that the number of moles of each compound is 0.005,
limiting reagent is 1.76 (CH​3​)​4​N​+​I​5​- ​and % yield is 63% yield.

Conclusion:
Overall, the procedure of synthesizing tetramethylammonium pentaiodide is we mix
tetramethylammonium iodide with iodine and ethanol together, heat the solution up, let it
cool down, put it in the ice bath and filter it the crystals. According to the result, weight of the
product is 1.12 g which is equal to 0.00158 mole, and 63 percent yield. The appearance of a
product is a dark green powdery substance.
References:
Ck12 Science(2016). ​Theoretical Yield and Percent Yield. Retrieved from
https://www.ck12.org/chemistry/theoretical-yield-and-percent-yield/lesson/Theoretical-Yield-a
nd-Percent-Yield-CHEM/

Libretexts(2014). Introduction to Chemical Bonding. Retrieved from

https://chem.libretexts.org/Core/Inorganic_Chemistry/Chemical_Compounds/Introduction_to
_Chemical_Bonding

Libretexts(2014). Types of Saturation. Retrieved from

https://chem.libretexts.org/Core/Physical_and_Theoretical_Chemistry/Equilibria/Solubilty/Typ
es_of_Saturation

Libretexts(2017). Vacuum Filtration. Retrieved from

https://chem.libretexts.org/Demonstrations_and_Experiments/Basic_Lab_Techniques/Vacuu
m_Filtration

Papiewski, J.(n.d.). Explain the Octet Rule & Give Examples. Retrieved from
http://education.seattlepi.com/explain-octet-rule-give-examples-6106.html