Lab Report

Synthesis of Tetramethylammonium Triiodide

Submit to
Dr. Patraphorn Sanguansat

By:
Apitta Kanchanapuping (Pao) 5961002
Kanlaya Charoenjarasrerk (Petch) 5961158
Koonlapat Singharerk (Pim)5961042
Nathapat Jaihow (Pooh) 5961039
Thunchanok Intachot (Earn) 5961100
Yanisa Wetchaporn (Anna) 5961208
Section 1107

General Chemistry
Mahidol University International Demonstration School
Semester 1 Academic year 2017 - 2018
 Abstract

Title : ​Synthesis of Tetramethylammonium Triiodide

Method : ​First, add 50 ml of Tetramethylammonium iodide into the beaker and use stirring
rod to grind them. Second, add iodine and ethanol into the beaker. Third, put it in the fume
hood and heat then with hot plate with low temperature to prevent premature crystallization.
Fourth, cool the beaker down with ice bath for 10 mins. Fifth, use vacuum filtration to collect
the crystal and wash them with hexanes. Sixth, air dry the product and weigh them.

Result :​ We got the result (specimen) in form of shiny crystal rod with the colour of wine.
 Introduction

This lab report shows the result and the analysis of the experiment of
tetramethylammonium triiodide synthesis. The purposes of the experiment is to synthesize
crystal from tetramethylammonium from two amount of iodine, study the differences of
crystallization between them and also to apply the knowledge of glassware, chemical
structure, balance and calculation.

Before doing this experiment, there are some background knowledges that we need to
know. The first one is chemical structure. According to Helmenstine (2017):
A chemical formula is an expression which states the number and type of
atoms present in a molecule of a substance. The type of atom is given using
element symbols. The number of atoms is indicated by a subscript following
the element symbol. (para. 1)
The chemical structure is based on the chemical formular, but the difference is that the
chemical structure is the three dimensional shape or configuration of a molecule. It is
like the visual of the chemical structure. This experiment involves the structure of
tetramethylammonium triiodide ( M e4 N + I 3− ) which is the combination of
tetramethylammonium iodide ( M e4 N + I − ) and Iodine ( I 2 ). We can write the chemical
formular as: M e4 N + I − + I 2 => M e4 N + I 3− and hence the chemical structure will be:

The structure determination can be applied to a range of targets from very simple molecules
such as diatomic oxygen or nitrogen, to very complex ones such as protein or DNA.
(Chemspider, n.d.)

A chemical equation is a written symbolic representation of a chemical reaction. The

reactant chemicals are given on the left-hand side and the product chemicals on the
right-hand side. The two are connected with an arrow leading from the left to the right,
symbolizing the reaction. The law of conservation of mass states that no atoms can be created
or destroyed in a chemical reaction, so the number of atoms that are present in the reactants
has to balance the number of atoms that are present in the products. (Wikihow, n.d.)
A mole simply represents Avogadro's number (6.022 x 1023) of molecules. A mole is
similar to a term like a dozen. If you have a dozen carrots, you have twelve of them.
Similarly, if you have a mole of carrots, you have 6.022 x 1023 carrots. In the equation above
there are no numbers in front of the terms, so each coefficient is assumed to be one (1). Thus,
you have the same number of moles of AgNO3, NaCl, AgCl, NaNO3.

Converting between moles and grams of a substance is often important. This conversion
can be easily done when the atomic and/or molecular mass of the substance(s) are known.
Given the atomic or molecular mass of a substance, that mass in grams makes a mole of the
substance. For example, calcium has an atomic mass of 40 atomic mass units. So, 40 grams
of calcium makes one mole, 80 grams makes two moles, etc.​ (Purdue Libraries , 2016)

Crystallization is the way that atoms gather to make tightly bonded or connected groups. It
separates a solid from a liquid or sometimes from a gas. Crystallization can be from a melt or
from a solution, and can be natural or artificial. Faster crystallization can make smaller
crystals as in basalt, and slower can make bigger ones as in granite. (Encyclopedia
Britannica,2016)
 Experiment

Materials-chemical
- Tetramethylammonium iodide ( M e4 N + I − ) 0.5g

- Iodine ( I 2 ) 0.6g

- 95% ethanol ( C 2 H 5 OH) 12 mL

- Hexane ( C 6 H 14 ) 2x7 mL
Equipment/glassware

- 50 mL beaker

- Spactula

- Weighing paper

- Stirring rod

- hot plate

- Ice bath
- Buchner funnel/funnel vacuum

- Filtration paper

- Weighing Paper

- Watch glass

- Electronic balance

- Capped vial
- Fume Hood
Procedures/flowchart
 Results

The result of the product we get is the crystal of tetramethylammonium triiodide. The
physical properties are dark purple or wine color, long and thin like rod shape of crystal. For
the chemical properties, the structure we get is M e4 N + I − + I 2 => M e4 N + I 3− The
theoreticcal yield is 1.0752804g. M e4 N + I 3− and the actual yield is 0.90 g. M e4 N + I 3−
Lastly, the percent yield is 83.7%.

Color:​ dark purple or wine when it is reflected with sunlight

Shape​: long, thin crystal rod shape

 Discussion

Molecular mass of M e4 N + I −

Molecular mass of I 2

∴ The limitting reagent is 1.0752864g. mol I 2

The excess reagent is 1.1322826 mol M e4 N + I −

2. Calculate the mass formed M e4 N + I −

5

limiting the percent yield

limitting reagent x molecular mass (product)

1.07528064 x ...g of

3. finding the percent yield

mass of the product from weigting:
Theoretical mass of product:
% Yield = ​Actual Yield​ * 100
Theoretical Yield

= 0.9 * 100
= 1.07528064

As a result, the percent yield is 83.7%

Discussion

Table 1​: Amount of Substances used in the experiment; both in grams and moles.
 Substance Grams Mole

Tetramethylammonium Iodide 0.50 1.1322826

Iodine 0.60 1.07528064

Tetramethylammonium 0.9 0.9

Triiodide
 Conclusion

This lab report has discussed about the synthesis of tetramethylammonium triiodide.
Based on the data, our percentage yield in this experiment is 83.7 This experiment allows us
to apply our knowledge to use proper glassware, study crystallization and the different
between two substances, calculate moles, weight of substance, and percentage yield.
 Suggestion

1. Be more careful during the process of grinding and crushing iodine.

2. Be careful using vacuum filtration
3. Make sure you hold the beaker in an ice bath without moving the substance.
 References
Britannica. (n.d.). ​Crystallization​. Retrieved from
https://www.britannica.com/science/crystallization.
Chemspider. (n.d.). ​Structure search​. Retrieved from
http://www.chemspider.com/StructureSearch.aspx.
Hallas, N. (2015, October 16). ​CRYSTALLIZATION​. Retrieved from
http://www.thermopedia.com/content/679/.
Helmenstine, A. M. (2017, April 4). ​Crystallize Definition (Crystallization)​. Retrieved from
https://www.thoughtco.com/definition-of-crystallize-605854.
Helmenstine, A. M. (2017, April 9). ​Definition of Chemical Formula​. Retrieved from
https://www.thoughtco.com/definition-of-chemical-formula-604906.
khanacademy. (n.d.). ​Limiting reagents and percent yield​. Retrieved from
https://www.khanacademy.org/science/chemistry/chemical-reactions-stoichiome/limiting-rea
gent-stoichiometry/a/limiting-reagents-and-percent-yield.
NCBI. (n.d.). ​PubChem​. Retrieved from https://pubchem.ncbi.nlm.nih.gov/search/search.cgi.
Organic Chemistry at CU Boulde. (n.d.). ​Crystallization​. Retrieved from
http://orgchemboulder.com/Technique/Procedures/Crystallization/Crystallization.shtml.
orgchemboulde. (n.d.). ​Crystallization​. Retrieved from
http://orgchemboulder.com/Technique/Procedures/Crystallization/Crystallization.shtml .
Purdue Libraries . (2016, January 13). ​Chemistry Lab Resources (for CHM 1XX and 2XX
Labs): Common Calculations​. Retrieved from
http://guides.lib.purdue.edu/c.php?g=352816&p=2377943.
Reciprocal Net. (n.d.). ​Crystallization​. Retrieved from
http://www.reciprocalnet.org/edumodules/crystallization/.
science uwaterloo. (n.d.). ​Excess and Limiting Reagents​. Retrieved from
http://www.science.uwaterloo.ca/~cchieh/cact/c120/limitn.html.
Wikihow. (n.d.). ​How to Balance Chemical Equations​. Retrieved from
https://www.wikihow.com/Balance-Chemical-Equations.