Lab report

Synthesis of tetramethylammonium triiodide

Date: 29/11/2017

​Nicha Ninnoennon 5961009

Nattamon Chungwatana 5961031
Vichayada Wanna 5961138
Sirada Vitoonvarakorn 5961141
Vachanon Ittikraichareon 5961170
Tiprada Kaveevorasart 5961214
 Table of contents

Abstract 2

Objective 2

Introduction 2​-3

Material 4​-5

Method 6

Results 7

Calculations 8​-9

Discussion 10

Conclusion 1​1

References 1​2

1
Abstract
During the lab experiment, we demonstrated the formation of Tetramethylammonium
triiodide using tetramethylammonium iodide and iodine as a reactant, and then we receive
tetramethylammonium triiodide for 0.81 grams through the process of crystallization and
filtration to purify solid compounds. After we mixed all ingredients, it is then placed in fume
hood and ice bath in order, then filter the product, dry, and weigh. This weigh, after go through
the calculation, it shows that iodine is the limiting reagent while tetramethylammonium iodide is
the excess reagent base on its weight that is more than iodine. Our product contains 75.7 percent
yield which is less than the actual yield, this might due to the error during the test. Overall, the
trial demonstrate the relationship between the mass of the reactant and the product which is
formed by a chemical reaction.

Objective
The purpose of this experiment is to synthesis tetramethylammonium triiodide which was
synthesised by a chemical reaction between tetramethylammonium iodide and iodine, dissolving
with Ethanol. The processes that perform throughout the experiment includes filtration and
crystallization. After the experiment, determining limiting reagent and excess reagent is
necessary and will use to identify the percentage yield as well. By doing this, the calculation of
actual weight of reactants and weight of products are needed in the procedure.

2
Introduction
In this experiment, several techniques such as stoichiometry (aka mass relationship),
crystallization, and filtration were being used to carry out with the experiment procedure.
To begin with, all atoms have a chemical structure of their very own. A chemical
structure is the number of atoms of the element in a compound. Each formula defines the actual
number of atoms in the elements, as well as how they are arranged and which ones were bonded
to another. ​(ThePD, 2017) ​Due to the fact that each chemical has its own shape, when writing a
chemical equation, we must balance out the number of atom.​ ​In the reaction, total charge and
mass must be the same for both of the reactants and products.
Stoichiometry is a technique which can be used to balance the chemical equation. Usually
chemical reactions were written off as an equation, with the reactants on the left side and the
products on the right side. In order to balance the equation, the number of the atoms on the left
side has to be the same with the one on the right. Raising coefficients is a common way to
balance the equations altogether. ​(T.E. Brown, 2008)
For example, the chemical reaction for the product of this experiment;
tetramethylammonium triiodide​, can be written as the following equation below:

M e4 N + I − + I 2 → M e4 N + I −3
For the calculation, molar mass can be find by calculating molecular mass using atomic
mass and then convert into molar mass (amu → g /mol ). In order to convert ​gram to mole​, the
mol of compound
formulae is: g of compound x molar mass of compound
and
mole to gram​ is: mol of compound x molar mass of compound
mol of compound
Our main objective in this experiment is to be able to calculate out the % yield, which is
the percent ratio of the actual product/actual yield comparing to the theoretical mass of the
product /theoretical yield. Both amounts of yields will not always be the exact same. So, to work
out the difference between these two, the % yield can be found by dividing the actual yield with
the theoretical yield, then multiples the result by 100%.​ (​Anne Marie Helmenstine, Ph.D. 2017).
actual yield
Percent yield ​= theoretical yield
× 100
As for the product, which is composed of several crystalline, could be formed thanks to
the process of crystallisation and filtration. Crystallisation is the process which involves
separation between solid and dissolved liquid or gas, allowing the atoms and the molecules to
gather and became a crystal ​(​L. Yu, S.M. Reutzel-Edens, 2013)​. ​While filtration is the process
where solid particles were being removed from liquid/gas via the filter, which is performed in the
experiment when we transfer the substance from the beaker into the capped vial, after filtrate
using a certain process of filtration called ‘vacuum filtration’. (​The Editors of Encyclopædia
Britannica, 2017).

3
 Material
● Tetramethylammonium iodide (0.5 -
g)

● Iodine (0.6 g)

● Ethanol 95% (12 mL)

● 50 mL Beaker

● Stirring rod

4
● Hot plate

● Ice bath

● Vacuum filtration

● Petri Dish

● Hexane

5
Method
1. Use a 50 mL beaker and add 0.5 g of tetramethylammonium iodide then use a stirring rod
to break up clumps.
2. Add 0.6 g of iodine and 12 mL of ethanol.
3. In the fume hood, gently heat the beaker on a hot plate with a stir bar 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.The crystals should
form during this time.
6. 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.
7. Using vacuum filtration, collect the crystals and wash them twice with hexanes (2´7 mL).
8. Air-dry the product and weight.

6
Results

Reactant Product

Name tetramethylammonium Iodine tetramethylammonium

iodide triiodide

Chemical formula M e4 N + I − I2 M e4 N + I 3−

Amount (gram) 0.50 0.60 0.81

Amount (mol) 2.488 x 10−3 mol 2.362 x 10−3 mol 1.780 x 10−3 mol

Actual yield - - 0.81 g

Theoretical yield - - 1.07 g

Percent yield - - 75.7 %

Reagent Excess Limiting -

Appearance - - Combination of dark

purple and green crystals

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Calculations

● Actual mass of reactant:

(CH 4 )3 N + I − = 0.5 g
I2 = 0.6 g

● Molecular weight
(CH 4 )3 N + I − + I 2 → (CH 4 )3 N + I 3−
Carbon = 12.001 amu
Hydrogen = 1.008 amu
Nitrogen = 14.007 amu
Iodine = 126.904 amu

(CH 4 )3 N + I − = 4(12.001) + 12(1.008) + 14.007 + 126.904

= 48.004 + 12.096 + 14.007 + 126.904
= 201.011 g/mol

I2 = 2(126.904)
= 253.808 g/mol

(CH 4 )3 N + I 3− = 4(12.001) + 12(1.008) + 14.007 + 3(126.904)

= 48.004 + 12.096 + 14.007 + 380.712
= 454.819 g/mol

● Number of mole
1 mol (CH 4 )3 N + I −
(CH 4 )3 N + I − = 0.5 g (CH 4 )3 N + I − × + − = 2.488 x 10−3 mol
201 g (CH 4 )3 N I
1 mol I 2 −3
I2 = 0.6 g I 2 × 254 g I 2
= 2.362 x 10 mol
+ −
1 mol (CH 4 )3 N I 3
(CH 4 )3 N + I 3− = 0.81 g (CH 4 )3 N + I 3− × = 1.780 x 10−3 mol
455 g (CH 4 )3 N + I 3−

● Excessive reagent
(CH 4 )3 N + I − =
1 mol (CH 4 )3 N + I − 1 mol (CH 4 )3 N + I −3 455 g (CH 4 )3 N + I −3
0.5g × 201 g(CH 4 )3 N + I −
× 1 mol (CH 4 )3 N + I −
× 1 mol (CH 4 )3 N + I −3
= 1.13 g (CH 4 )3 N + I 3−

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● Limiting reagent
1 mol I 2 1 mol (CH 4 )3 N + I −3 455 g (CH 4 )3 N + I −3
I2 = 0.6g × 2.54 g I 2 × 1 mol I 2 × 1 mol (CH 4 )3 N + I −3
= ​1.07 g (CH 4 )3 N + I 3− ← ​Theoretical yield
● Percentage yield
actual 0.81
theoretical yield × 100 ​= 1.07 × 100 = ​75.7% Yield

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Discussion
Chemical equation: M e4 N + I − + I 2 → M e4 N + I 3−
In synthesis of tetramethylammonium triiodide experiment, the reactants in this reaction
are tetramethylammonium iodide ( M e4 N + I − ) and Iodine ( I 2 ) which will give
tetramethylammonium triiodide ( M e4 N + I 3− ) as a product.
In the beginning of the experiment, we use 0.50 grams of tetramethylammonium iodide
and 0.60 grams of iodine. The mole of M e4 N + I − is 2.488 x 10−3 mol and the mole of I 2 is
2.362 x 10−3 mol.
For the product, which is tetramethylammonium iodide weighed 0.81 g and the mole is
1.780 x 102 mol.
In the chemical reaction, ​limiting​ ​reagent​ is the reactant used up first in the reaction.
Another reactant is called ​excess reagent​ is the reactant in quantities greater than necessary to
react with the limiting reagent, shortly, it’s the left over after limiting reagent is used up. In this
experiment, the limiting reagent is Iodine as the amount is 1.07g M e4 N + I 3− , which is less than
the amount of tetramethylammonium iodide that is equal to 1.13g M e4 N + I 3− .
The theoretical yield is the amount of the product in grams formed from the limiting
reagent (CSUN), and from the calculation above, our theoretical yield is 1.07 g which we expect
this amount for the tetramethylammonium in total. However, our actual yield is 0.81 g which can
calculate into 75.7 percent yield and this is less than the expectation. Percent yield can be
calculated by dividing the actual yield by theoretical yield then time with 100. The error that
happened may cause by several unpreventable factor. Actually, the product of our experiment
should be completely purple, however it shown up by having some spot that contain green color
of the product. Some reactant might remain unreacted, or that some product are lost during
transferring from the beaker into the filtration process (​BBC, 2014​). Also, maybe the product
didn’t cool down enough during the ice bath process, which can causes some small pieces of
crystal that are small enough to pass through the filter paper.
In order to fix this error, we need to be more careful on the experiment and make sure to
do every process and use the amount to reactant accurately, also prevent the leaking out of the
product. We need to aware about temperature and disturbance during crystallization because
increasing temperature increases the disorder of reagent molecules. Such manipulations may
have an impact on interactions which control nucleation and crystal growth. In addition, such
interactions may have an impact on crystal packing as well as the termination of crystal growth
(​Hampton, 2016​). The step that need to concern about contaminate is during the filtration
because we have to make sure that there is no substance left over from other groups, so the
product won’t get mix up. Also throughout the experiment, we need to wear gloves, lab coat, and
goggles to prevent our skin contaminating with the substances. Furthermore, we should repeat
the experiment several time in order to get the accurate data for the amount of products.

10
Conclusion
According to the experiment, the product is synthesized by using 0.5g (2.488 x 10−3 mol)
of tetramethylammonium iodide and 0.6 g (2.362 x 10−3 mol) of iodine as a reactant and we get
0.81g (1.780 x 10−3 mol) tetramethylammonium triiodide for a product that calculate into 75.7
percent yield which is less than the actual product. The appearance of our product is the mixture
of largely purple and minimally green crystal. The limiting reagent is iodine as the amount is
1.07g (CH 4 )3 N + I 3− , which is less than tetramethylammonium iodide that has 1.13g
(CH 4 )3 N + I 3− .

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References

http://www.csun.edu/~hcchm001/LIMITREG.pdf. (n.d.).

Http://www.bbc.co.uk/schools/gcsebitesize/science/add_ocr_gateway/chemical_economics/atom

ec

onomyrev1.shtml. (n.d.).

Helmenstine, P. A. (n.d.). What Is a Balanced Equation in Chemistry? Definition and Examples.

Retrieved December 06, 2017, from

https://www.thoughtco.com/definition-of-balanced-equation-and-examples-604380

Helmenstine, P. A. (n.d.). What Is Percent Yield? Review Your Chemistry Concepts. Retrieved

December 06, 2017, from https://www.thoughtco.com/definition-of-percent-yield-605899

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