Iodoform

(Pilapil, Jean Diane Rose T.)

The goal of this experiment is to synthesized and know the mechanism of how iodoform could be
obtained from acetone and potassium iodide. It was performed in a round-bottomed flask with a
solution of potassium iodide, water and acetone. Sodium hypochlorite was added to the prepared
solution with frequent shaking until precipate was formed completely. It was decanted to obtain the
crystals, washed with distilled water and filtered by suction. It was purified by using warm methanol.
Water was added to the filtrate collected until light yellow crystals were formed. It was the filtered with
suction, washed thorough with distilled water and was dried. The light yellow crystals obtained was
iodoform. The percentage yield obtained was 24.22%.

Introduction
Iodoform, or triiodomethane (CHI3) is
yellow crystalline with a relatively high molar
mass due to the iodine atoms. Incompatible with strong oxidizing agents,
reducing agents.
May explode when heated. It is harmful
if swallowed, inhaled or absorbed through skin
and causes irritation to skin, eyes and
respiratory tract. Iodoform is also affects
cardiovascular system, central nervous system,
Figure 1. Iodoform in 3-D
liver and kidneys.
It is therefore a solid at room
temperature It melts at 119°C and is very When released into the soil, iodoform
slightly soluble in water and soluble in ether or may leach into groundwater. When released
ethanol. A visible precipitate of this compound into water, it may evaporate to a moderate
will form from a sample only when a methyl extent and it is expected to have a half-life
ketone is present. between 1 and 10 days.

This type of reactivity conforms to the Iodoform has an estimated

more general Haloform Reaction (Ölmez, 2009). bioconcentration factor of less than 100. This
Iodoform was formerly used as an material is not expected to significantly
antiseptic. It is a stable compound. bioaccumulate. When released into the air, it
may be moderately degraded by reaction with
photochemically produced hydroxyl radicals
and it is expected to have a half-life of greater
than 30 days (Ölmez, 2009).

Figure 2. Halogenation Reaction

Experimental Method The crystalline precipitate was allowed to
settled and it was decanted. The crystals were
Apparatus washed two to three times with distilled water.
It was filtered with suction while pressing the
The apparatuses needed were round-bottomed cystals as dry as possible to the filter paper. The
flask, separatory funnel, buchner funnel, 100- crude iodoform was purified by dissolving the
mL beaker, stirring rod, 10-mL and 1-mL pipet, damp product in slightly more than the
iron stand with iron ring and electric stove. necessary amount of hot methanol. It was then
Chemicals filtered while the solution is hot to remove
insoluble impurities. The filtrate was added with
The chemicals needed were potassium iodide, water until the iodoform was completely
acetone, sodium hypochloriteand methanol. precipitated as light yellow crystals. The
reaction was heated to coagulate the crystals. It
was cooled thoroughly and crytals were
Procedure collected on the filter paper with suction.

A solution of 3.2 g of potassium iodide (KI), 62 The crystals were washed with distiiled water
mL of water and 0.8 mL of acetone was placed and allowed it dry. It was weight after drying.
in a round-bottomed flask. In a separatory
funnel, a dilute sodium hypochlorite (“chlorox”)
was poured out. The separatory funnel was Results
set-up properly on the iron ring which was Table 1. Description of Starting materials
attached to the iron stand. A dilute solution of Starting Materials Description
sodium hypochlorite was poured into the a. Potassium iodide White crystalline solid
separatory funnel. The dilute hypochlorite Molar mass: 166.0028 g/mol
b. Acetone Colorless liquid with a distinct
solution was added to the solution of potassium
smell, density – 0.791 g/mL
iodide and acetone as long as precipitate were c. Sodium Colorless liquid commonly
formed completely. hypochlorite known as bleach/chlorox,
density – 1.11 g/mL

Table 2. Description of the product

Product Description
Iodoform A bright yellow powder or
(triiodomethane) crystals. It has a penetrating
odor and has a smooth
texture or appearance.

Source: google.com
 Source: google.com
Calculations:

Moles of Acetone used:

Chemical Reaction involved
C3H6O + 3 NaClO + 3 KI → CH3COCI3 + 3 NaOH + 3 KI 0.791 g ( mol
0.80 mL ( ) )
CH3COCI3 + OH → CHI3 + CH3COO- mL 58.07 g C 3 H 6 O

= 0.011 mol C3H6O

Table 3. Calculation of Percentage Yield Mole ratio of acetone and methyl iodide is 1:1,
Weight of first filter paper (g) 1.1895 thus yields to 0.011 mol CHI3.
Weight of Iodoform obtained in 0.1683
the first filter paper (g) Moles of Potassium iodide used:
Weight of second filter paper (g) 1.1661 mol
Weight of Iodoform obtained in 0.4444 3.20 g ( )
166.0028 g KI
the second filter paper (g)
Net weight of Iodoform 0.6127 = 0.019277 mol KI
obtained (g)
Moles of potassium iodide (KI) 6.43x10-3 The mole ratio of potassium iodide and methyl
used (mol) iodide is 3:1, thus this yields to 6.43 x 10 -3 mol
Moles of acetone (C3H6O) used 0.011 CHI3.
(mol)
Theoretical weight of Iodoform
(g)
2.52987 0. 019277 mol KI ( 13molmolCHKII )
3

Actual/Experimental weight of 0.6127

Iodoform (g) = 6.43 x 10-3 mol CHI3.
Percentage Yield 24.22 %
Theoretical weight of Iodoform:
393.718 g CH I 3
6.43 x 10-3 mol CHI3 ( )
mol

= 2.52987 g CHI3

Percentage Yield:
Reaction Mechanism
 0.6126 g
% Yield = x 100
2.52987 g
% Yield = 24.22 %

Discussion

Haloform Reaction is the reaction that The first two steps were repeat twice
has been used in qualitative analysis to indicate more yielding the trihalogenated ketone.
the presence of a methyl ketone (“Haloform (Ölmez, 2009).
reaction,” n.d., para. 1).

Lots of ketones give this reaction, but

those that do all have a methyl group on one
side of the carbon-oxygen double bond. These
are known as methyl ketones.

The halogen reaction occurs when The hydroxide now reacts as a

methyl ketones are treated with the halogen in nucleophile at the electrophilic carbonyl
basic solution, polyhalogenaton followed by carbon, with the C=O becoming a C-O single
cleavage of the methyl group occurs. bond and the oxygen is now anionic.

In the beginning step, of an acid-base Reform the favourable C=O and

reaction the hydroxide functions as a base and displace a leaving group, the trihalomethyl
removes the acidic α-hydrogen giving the system which is stabilized by the 3 halogens.
enolate. This gives the acetic acid. In an acid-base
reaction, the trihalomethyl anion is protonated
by the acetic acid, giving the acetate and the
haloform (trihalomethane).

The nucleophilic enolate reacts with the

iodine giving the halogenated ketone and an
iodide ion. After preparing the solution of
potassium iodide (KI) and acetone (CH3COCH3),
sodium hypocholorite (NaClO) was added drop
by drop and a dark color was observed with a
little yellow precipitation. The sodium While the solution is left to cool, which
hypochlorite serves as the giver of hydroxide will form the yellow iodoform crystals. Distilled
ion that acts as a nucleophile. The hydroxide ion water was added until precipitation of
attacks the carbonyl atom to form a iodoform was completed.
halogenated ketones. The dark color in every
drop showed that the reaction is carrying on. The overall reaction mechanism:
Continuous addition of sodium hypochlorite
until the dark color can not be seen enables to
finish all acetone and form iodoform (Ölmez,
2009).

It was observed that iodoform was a

pale yellow crystalline. The precipitation that
we observed at the bottom of the flask.

The purpose of the addition of distilled

water immediately after the yellow crystals
formed was to possibly dilute the sodium
hypochlorite and to prevent excess hydrolysis
In calculating the percentage yield, the moles of
velocity iodoform formed. The obtained yellow
acetone and potassium iodide used was
crystals was added with water and immediately
calculated. The moles of acetone used was
filtered with a Buchner funnel. Then the crystals
0.011 mol and the moles of potassium iodide
were washed until the filtrate do not react
used was 0.019 mol. The limiting reagent was
alkalis, or free NaClO as the rest of NaClO in the
indentified to be the potassium iodide. A
crystalcan cause decomposition of iodoform on
limiting reagent is the reactant that limits the
crystallization time with alcohol (Liapril, 2013).
chemical reaction; the one that produces less
product is the limiting reagent (Shah, 2014). It
After filtration with a Buchner funnel
was computed by using stoichiometric ratio of
and recrystallization (purification) was
the balanced chemical reaction. The potassium
performed. Recrystallization is a purification of
iodide was the limiting reagent because it yields
solids which dissolve in hot conditions of a
6.43x10-3 moles, the least amount of iodoform
particular solvent, but in the cold or at room
produced in the reaction. The theoretical yield
temperature, or crystal substance will occur. In
was 2.53 g and the experimental yield was
this experiment used solvent methanol.
0.6127 g. Given the data, the percentage yield
calculated was 24.22%.
Iodoform then dissolved in few volume
of methanol. The yellow precipitate left in the
filter paper was the impurities. Once iodoform
was diluted with methanol, it was heated. The
heating aims to assist the process of dissolution
between methanol and iodoform (Liapril, 2013).
Conclusion and Recommendation Liapril, J. Iodoform. 2013. Retrieved from:
https://www.scribd.com/doc/139967298/Iodof
It was concluded that iodoform was synthesized orm-Organic
by halogenation reaction. The general rule for
determining compound which will give Ölmez, Hilmi. 2009. Retrieved from:
iodoform is the presence of aldehyde or ketone. http://raporlarim.blogspot.com/2009/10/iodof
Ethanal is the only aldehyde to give the orm.html
triiodomethane (iodoform) reaction. For the
ketones, only those that do all have a methyl
group on one side of the carbon-oxygen double
bond.

The possible causes of error was

transferring of solutions from one container to
another the possibily altered the amount of
chemicals used during the experiment. Another
is the recrystallization by the use of methanol
because some of the iodoform was not drained
off as filtrate due to impurities acquired. Lastly,
is the filtration process because the filter paper
used in the experiment has a hole in one of its
side that possibly drained some of the iodoform
crystals that yields to low percentage yield.

It is recommended that proper transfering must

be practiced well for minimal alteration of the
chemicals used in experiment.And the addition
of sodium hypochlorite must be precise to make
sure that the precipitate is formed competely.

References

Haloform Reaction. Retrieved from:

http://www.organic-
chemistry.org/namedreactions/haloform-
reaction.shtm

Hunts,Ian. Enols and Enolates. University of

Calgary Retrieved from:
http://www.chem.ucalgary.ca/courses/350/Car
ey5th/Ch18/ch18-3-2b.html