DELHI PUBLIC SCHOOL

VARANASI

CHEMISTRY INVESTIGATORY PROJECT

Preparation of
Iodoform
 CERTIFICATE
This is to certify that, Shiwansh Kumar
Gupta a student of class XII-D2 of
academic year 2021-2022 has
successfully completed the
investigatory project on given topic
“Preparation of Iodoform- Study of it’s
properties and uses” under the
guidance of Dr. Vinay Pandey during
year 2021-2022.

______________ _______________
DR. VINAY PANDEY EXTERNAL INVIGILATOR

______________ _______________
MRS.NILANGANA MR.ANURAG PANDEY
CHAKROVERTY
ACKNOWLEDGEMENT
First and foremost, I would like to thank our
Chemistry Teacher Dr. VINAY PANDEY who
guided us through doing these projects. He
provided us with invaluable advice and
helped us in difficult periods. His motivation
and help contributed tremendously to the
successful completion of the project.
Besides, I would also like thank our senior
wing coordinator Dr. MUKTI PANDEY and all
the teachers who helped us by giving us
advice and providing the equipment which
we needed.

Also I would like to thank my family and

friends for their support. Without that support
we couldn’t have succeeded in completing
this project.

At last but not in least, we would like to

thank everyone who helped and motivated
us to work on this project.
INDEX……………
✓ Aim
✓ Background
✓ Chemical Required
✓ Equipment Required
✓ Procedure
✓ Observation
✓ Theory
✓ Calculation
✓ Conclusion
✓ Precaution
 Aim :
Preparation of Iodoform
Background
Functional group transformations allow the
conversion of a functional group to
transformations an aldehyde or a ketone without
affecting the carbon skeleton of the molecule.
Aldehydes can be synthesized by the oxidation of
primary alcohols, or by the reduction of esters,
acid chloride, or nitriles. Since nitriles can be
obtained from alkyl halides, this is a way of adding
an aldehyde unit (CHO) to an alkyl halide. Ketones
can be synthesized by the oxidation of secondary
alcohols. Methyl ketones can be synthesized from
terminal alkynes.

According to Rashid alcohol with one hydrogen

that chains at carbon as a bring of carbonyl group
can be oxidized become carbonyl compounds.
primary alcohols that can be oxidized with
carboxylic acid and become acid. Secondary
alcohol-producing ketone and tertiary alcohol can
be oxidized:
 H O O
| || ||
R — C — OH —> R — C — H —> R — C — OH
|
H
Primary alcohol aldehyde acid R’ R’

R — C — OH —> R — C — R
| ||
H O
Secondary alcohol Ketone

Most acidic protons are attached to heteroatoms4

like hydrogen, oxygen, and nitrogen. Protons
attached to carbon are not normally acidic but
there are exceptions. One such exception occurs
with aldehydes or ketones when there is a CHR2,
CH2R, or CH3 group next to the carbonyl group.
The protons indicated are acidic and are attached
to (alpha) carbon. They are therefore called
protons. A lone pair of hydroxide oxygen forms a
new bond to a proton. Simultaneously, the C-H
bond breaks. Both electrons of that bond end up
on the carbon atom and give it a lone pair of
electrons and a negative charge (carbanion).
However, carbanions are generally very reactive,
unstable spices that are not easily formed.
Therefore, some form of stabilization is involved
here.
According to Fessenden chaining of carbon-
hydrogen bonding is usually stable, non-polar, and
non-acidic properties. But with there in one group
carbonyl happening alpha hydrogen that has
acidic properties. If one hydrogen has the alpha
position to two carbonyl groups so its hydrogen is
so acidic can form a salt with synthetic compound
alkoxide.
As for the reaction:

O O
|| ||
CH3CCH3 CH3CCH2CCH2
Acetone Ethyl acetoacetate

pKa = 20 pKa = 11

According to Tin Doesen, a compound that

contains the CH3CO group or that produces this
group, if oxidized in one condition. For example,
acetaldehyde CH3CHO form ethanol CH3CH2OH
react with sodium hypochlorous forming
iodoform.
 O O
|| ||
R — C — CH3 + NaClO —> R — C — Cl3 +

3NaOH

O O
|| ||
R — C — CI3 + NaOH —> R — C — O-Na+ +

CHI3

OH O
| ||
R — C — CH3 + NaOI —> R — C — Cl3 +

H 2O

OH O
| ||
R — C — CI3 + NaOI —> R — C — O — Na+ +

CHI3 + H2O
According to Miller, the radical initially produced
by the homolytic decomposition of a di-alkyl
peroxide can undergo further scission. The rate of
scission depends on the temperature and the
stability of the resulting radical. For example,
butoxy radicals decompose on heating to methyl
radicals and acetone:

BuO —> CH3 + CH3COCH3

Chemicals required
o Potassium Iodide (KI) solution
o Acetone (CH3COCH3) solution
o Sodium hypochlorous (NaClO) solution
o 1-propanol (CH3CH2CH2OH) solution
o Dioxane (C4H8O2) solution
o Sodium hydroxide (NaOH) 1% solution
o Potassium Iodine Iodide (KI.I2) solution
o Ethyl acetoacetate (CH3COH2COOC2H5)
solution
o Acetophenone (C6H5COCH3) solution
o Aquadest (H2O)
Materials required
o Whatman filter paper
o Aluminum foil
o Capillary tube
o Matches
o Dropping pipette
o Electric scale
o Graduated cylinder 100 ml
o Graduated cylinder 10 ml
o Stir bar
o Büchner funnel
o Beaker glass 250 ml
o Oven
o Erlenmeyer 500 ml
o Thiele equipment
o Bunsen burner
o Test tube
o Test tube stand
o Test tube holder
o Triangle
o Asbestos gauze
o Spray flask
o Soft and Rough cloth
 Procedure
Synthesis of iodoform

I. 6g of KI was balance by electric scale

II. It was added by water 100ml in glass beaker
III. It was added by acetone 2ml and closed by
aluminium foil on acidic cupboard.
IV. It was added by NaClO 65ml with slowly and
stirred until the mixture change colour to
greenish yellow solution.
V. It was let stand until 10 minutes in acidic
cupboard.
VI. Then it was filtered by Büchner funnel.
VII. Afterwards, it was rinsed by water until the
precipitate in the beaker glass is loss.
VIII. The residue(crystal) was taken and it was dried
in the oven.
IX. It was balanced by electric scale.
X. It was filled into capillary tube and the melting
point was determined.
Iodoform Testing

A. 1-propanol test
o 5 drops of 1-propanol was dropped into test
tube.
o It was added by dioxane 5ml.
o It was added by 1ml of NaOH 1% until form 2
layers.
o It was added by some drops of KI.I2 until the
colour change to brown.
o It was added by 20 drops of NaOH.
o It was divided into two observation, namely
heated and let stand.

B. Ethyl acetoacetate test

o 5 drops of ethyl acetoacetate was dropped
into test tube.
o It was added by dioxane 5ml.
o It was added by 1ml of NaOH 1% until form 2
layers.
o It was added by some drops of KI.I2 until the
colour change to brown.
o It was added by 20 drops of NaOH.
o It was divided into two observation, namely
heated and let stand.
C. Acetophenone test
o 5 drops of acetophenone was dropped into
test tube.
o It was added by dioxane 5ml.
o It was added by 1ml of NaOH 1% until form 2
layers.
o It was added by some drops of KI.I2 until the
colour change to brown.
o It was added by 20 drops of NaOH.
o It was divided into two observation, namely
heated and let stand.
Observation
S. Experiment Observation
No.

Synthesis of Iodoform

1. KI(g) was balanced on electric 6g of KI

scale

2. It was added in glass beaker 100ml of water

with water

3. Acetone was added 2ml of acetone

4. NaClO was added by dropper 65ml of NaClO

and stirred greenish yellow
mixture

5. It was let stand until 10 Separate:

minutes in cupboard -Transparent soln
-Greenish yellow
ppt

6. It was filtered by Büchner Get yellow crystal

funnel
7. The crystal dried in oven Pre dry crystal

8. It was balanced on electrical Weight: 1.1g

scale

9. It was filled in capillary tube Temperature:

and determined its melting 120oC to 124oC
point
 Iodoform Test

A. 1-propanol test

1-propanol 5 drops of
1-propanol

It was added by dioxane 5ml of dioxane

It was added by NaOH 1% 1ml NaOH, forms 2

layer
-Transparent soln
-turbidity soln

It was added by KI.I2 Brown solution

It was added by NaOH 20 drops of NaOH

It was divides into 2 parts:

-Heated -Transparent soln
-Let stand -Dark Yellow soln
B. Ethyl acetoacetate test

1-propanol 5 drops of
1-propanol

5ml of dioxane
It was added by dioxane
1ml NaOH, forms 2
It was added by NaOH 1% layer
-Transparent soln
-turbidity soln

It was added by KI.I2 Brown solution

20 drops of NaOH
It was added by NaOH

It was divides into 2 parts:

-Heated -Yellow solution
-Yellow solution
-Let stand
C. Acetophenone test

Acetophenone 5 drops of
Acetophenone

It was added by dioxane 5ml of dioxane

It was added by NaOH 1% 1ml NaOH, forms 2

layer
-Transparent soln
-turbidity soln

It was added by KI.I2 Brown solution

It was added by NaOH 20 drops of NaOH

It was divides into 2 parts:

-Heated -Yellow solution
and white ppt

-Let stand -Yellow solution

Theory
In this experiment, that had been done of
balancing the KI as the main compound in.
Iodoform synthetic that dissolved with H2O and
added by acetone and NaClO with slowly. As the
function of KI to react with NaClO to form KCl
and NaOI. As the function of NaClO addition
with slowly is to react with perfectly.

KI + NaClO —> KCl + NaOI

NaOI will be decompose in become to NaO+ and

I-. Addition of acetone as function to react with
the ion I- with NaO+ and H+,and the solution is
let stand. So that forming CH3COONa
solution(carboxylic salt) and CHI3 (Iodoform)
from acetone compound. As the function of
kept solution in acidic cupboard is the
precipitate that precipitated in the bottom of
glass beaker and the compound is not
evaporating in atmosphere. The reaction is as
follows:
Step 1:
O O
|| ||
CH3 — C — CH3 + KI + NaOCl —> CH3 — C — CH3

+ KCl + NaOH
Step 2:
O O
|| ||
CH3 — C — CH3 + NaOI —> CH3 — C — CH2 — I

+ NaOH
Step 3:
O O
|| ||
CH3 — C — CH2I + NaOI —> CH3 — C — CHI2

+ NaOH
Step 4:
O O
|| ||
CH3 — C — CHI2 + NaOI —> CH3 — C — CHI3

+ NaOH
Step 5:
O O
|| ||
CH3 — C — CHI3 + NaOI —> CH3 — C — O-Na+

+ CHI3
Precipitated solution is filtered by Büchner
funnel so that the crystal that is being obtained
become dry fast. Crystal then put into the oven
so that the drying process more fast and
evaporating the left of after that contain in
crystal. The colour of iodoform crystal is yellow.
Crystal that obtained from recrystallisation
because it has form an iodoform crystal
reviewed from it colour, smell and it’s melting
point. The weight of crystal is 1.1 g and
rendement is 10.34%, so if crystal is
recrystallised again, it can produce less weight
than 1.1g. As the melting point of iodoform
crystal is 120o-124oC. This is same wit h theory
that the melting point of iodoform is 123oC.
Least amount of rendement is obtained
because there is iodoform in filtrate and much
of the iodoform that evaporated when stand
was kept still in acidic cupboard and also the
stirring way of solution at the NaClO addition.
Calculation
Acetone (molecular weight) = 0.782 g/ml
Acetone = 58g/mol
Acetone (volume) = 2ml
Iodoform (molar weight) = 373.79 g/mol
Iodoform(obs) (mass) = 1.1 g
Problem:
Rendement……?
Solution:
Mass acetone(n) = (molar weight x volume) acetone
= 0.782 g/ml x 2ml = 1.584g
______________________________
______________________________
= 0.027 mol
1 Mole of acetone = 1 Mole of iodoform
Mass of iodoform(the) = mass acetone x molar mass
of iodoform
= 0.027 mol x 393.79 g/mol
= 10.63 g
= 10.32 %
Conclusion
Based on the experiment they had been done, so it
may be conclude that :

(A) The principal of isolation of isolation of organic

compound (EPMS) of phenylpropanoid form
galingale are maceration, separation,
extraction and purification.

(B) The isolation technique in galingale can be

obtained with maceration way, separation and
purification.

Precaution
1. We should be more careful while doing this
experiment.

2. We should be more compact with friends group.

Bibliography

www.google.com

www.byjus.com

www.vedantu.com

www.sinspid.com

www.zoro.to

Chemistry class 12 NCERT textbook