RATIFICATION PAGE

Complete report of Organic Chemistry II with title “Synthetic of

Iodoform” by:
Name : Nana Nursana Ahda
Student ID : 200105512001
Class : ICP of Education Chemistry
Group : I (One)
has been checked and revised by Assistant and Assistant Coordinator, so this
report considered accepted.

Makassar, Oktober 2021

Assistant Coordinator Assistant

Nur Rahma Amar S,pd. Nur Rahma Amar S,pd.

Known by
Responsible Lecturer

Hardin, S.Si, S.Pd, M.Pd

NIP. 19870807 201504 1 004
A. TITLE OF EXPERIMENT
Synthetic of Iodoform
B. OBJECTIVE OF EXPERIMENT
In this experiment student hope can understand about:
1. Work principal and Cristallization techniques in solid organic substance.
2. Haloform reaction.
3. Haloform reaction function in preparation of haloform and carboxylic
acid and to show the existence of CH3CO and CH3CHOH.
C. LITERATURE REVIEW

Crystallization or crystallization is the event of the formation of solid

particles (crystals) in a homogeneous phase. Crystallization is a practical method
for obtaining pure chemicals under conditions that meet the requirements for both
packaging and storage.In the crystallization process, usually using a tool called a
crystallizer. Crystallizer is a tool used to obtain or make crystals from the
solution. Therefore, the solution to be crystallized must be supersaturated first by
evaporation or cooling. Crystallization cannot occur without super saturation first,
where how to obtain this saturation depends on the solubility (Yulianto, dkk
2018 : 45).

Crystallization may occur as the formation of solid particles in steam, as in

the formation of snow; as solidification in molten water. Crystallization is also a
solid-liquid separation process, in crystallization there is a change in the solute
mass from a pure density liquid solution in the crystalline phase ( Pinalla 2011 :
66).

The ease with which a precipitate can be filtered and washed depends to a
large extent on the morphological structure of the precipitate, namely the shape
and sizes of its crystals. The larger the crystals that form during precipitation, the
easier they can be filtered out and probably (though not necessarily) the faster the
crystals will drop out of solution, which will again aid filtration. The shape of the
crystal is also important. Simple structures such as cubes, octahedrons, or needles
are very advantageous, because they are easy to wash after filtering. Crystals with
more complex structures, which contain grooves and holes, will retain the mother
liquid, even after careful washing. With a precipitate consisting of such crystals,
quantitative separation is less likely to be achieved ( Pinalla 2011 : 65).

Basically the recrystallization event is related to the precipitation reaction. A

precipitate is a substance that separates from one solid phase and exits into
solution. A precipitate is formed when the solution is too saturated with the
substance in question ( Pinalla 2011 : 65).

Crystallization can only take place in supersaturated solutions. To obtain a

supersaturated solution, it can be done in several ways, including: cooling the
solute with decreasing solubility with decreasing temperature, evaporation of the
solution using heating, adiabatic evaporation of the solution, salting out, namely
the addition of substances that can reduce solubility, chemical reactions to form
crystal masses, or by electrochemistry (Prassanti, Guswita 2018 : 62).

In principle, crystallization is formed through two stages, namely, nucleation

or the formation of crystal nuclei and crystal growth. The driving factor for
nucleation rate and crystal growth rate is supersaturation. Neither nucleation nor
growth can take place in saturated or unsaturated solutions. Crystal nuclei can be
formed from different types of particles: molecules, atoms or ions. due to the
movement of these particles, particles may form a cluster or cluster, the cluster
which is sufficient to form an embryo at a high saturated fat state the embryo
forms a crystal nucleus( Pinalla 2011 : 126).

The Haloform reaction (also known as the Lieben iodoform reaction or

Lieben haloform reaction) describes the two-step conversion of a methyl ketone 1
to a carboxylic acid via threefold halogenation to the trihaloketone 2 foilowed
by base-cleavage to carboxylate 3 and haloform 4. Acidification affords the
carboxylic acid 5.
An important variation is that compounds such as methyl carbinols also undergo
the Haloform reaction since they are typically oxidized to the corresponding
methyl ketone under the reaction conditions. This reaction is particularly
well known to undergraduate organic chemistry students as the "Iodoform Test"
in qualitative organic chemistry (Li 2007 : 610).
The Haloform reaction has a long and rich history, summarized
exhaustively by Fuson and Bull' and by Parkin. Interestingly, the initial
discoveries of the Haloform reaction all involved the treatment of ethanol with
iodine, chlorine, or bromine in the presence of alkali to afford the respective
haloform following in situ oxidation of ethanol to acetaldehyde. Indeed,
chloroform was used extensively in the U.S. Civil War as a battlefield anesthetic
during amputations. The now well-known "Iodoform Test" was inaugurated in
1870 by Lieben. will be presented later, nature produces enormous quantities of
chloroform and bromoform, most probably involving the Haloform reaction (Li
2007 : 610).
Methyl ketones typically undergo halogenation three times to give a trihalo
ketone due to the increased reactivity of the halogenated product as discussed
above. This trihalomethyl group is an effecive leaving group due to the three
electron withdrawing halogens anad can be cleaved by a hydroxide nion rto effect
the haloform reaction. The product of hhis reacion is a carboxilate and a haloform
molecule (CHCl3, CHBr3, CHl3). Overall the haloform reaction represents an
effective method for the conversation of the methyl ketones to carboxylate acids.
Typically, this reaction is performed using iodine because the subsequent
iodoform (CHl3) is bright yellow solid which is easily filtered off.
Example for general reaction:
 (Park, dkk 2019 :
340).
Activation of the methyl C−H bonds by the adjacent electronwithdrawing
carbonyl group allows electrophilic substitution of these hydrogen atoms by active
chlorine from sodium hypochlorite. The haloform reaction is a redox reaction in
which hypochlorite acts as the oxidizing agent. Formally, the methyl group carbon
is oxidized with chlorine(I). The introduced electronegative chlorine atoms
increase the acidity of the protons on the α-carbon of the mono- and dechlorinated
ketone intermediates and ensure their further chlorination. Strongly basic NaOH,
second product substitution (Kmentova, dkk 2020 : 2).
Iodoform test. Methyl ketones and acetaldehyde, ie compounds containing
the Me-CO- grouping, gave a positive iodoform reaction. Alcohols having the
Me-CH(OH)-R structure, which are oxidized to methyl ketones, also slowly give
a positive test. The test is positive if a yellow precipitate of iodoform is deposited.
Filter the yellow precipitate, dry on filter paper and determine the m.p. melting
point of iodoform (Furniss, dkk 1989 : 1220).
Iodoform is obtained by the action of iodine on ethanol (ethyl alcohol), Of
on propanone (Acetone) in the presence of an alkali. this reaction is called
haloform reaction and is comony know as iodoform test. Example iodoform net
reaction from aceton : iodoform can also be prepared by warning acetone with
iodine in the presence of an alkali. The reactions are:

Iodination of acetone.
 Hydrolysis (cleavage) of Cl3 – CO – CH3 by alkali.

(Arora 2006 : 226).

Iodoform is triiodomethane a yellow crystalline solid belongs to the family

of organic halogen compounds used as an antiseptic component of certain
medications. It was first prepared in 1822 by electrolysis of aqueous solutions of
acetone, inorganic iodides and sodium carbonates(Singh, dkk 2012 : 321).

It s antiseptic action discovered in 1880, which made it an important

medicinal. It has no irritant action; it has antiseptic, disinfectant properties. The
release of elemental iodine when applied to the tissue which has a mild
disinfectant action with the organic tissue, iodine is slight irritant to the tissue
which may promote granulation tissue formation (Singh, dkk 2012 : 321).

Iodoform, also known as triiodomethane, is a yellow crystalline solid which

belongs to the family of organic halogen compounds used as an antiseptic
component for certain medications. It was first prepared in 1822 by electrolysis of
aqueous solutions of acetone, inorganic iodides and sodium carbonates. Its
antiseptic action was discovered in 1880, which made it an important medicinal
compound. Its beneficial effects on the tissue of the wounds are due to its
protecting power both mechanically and maintaining asepsis thus promoting faster
healing. It destroys the toxic substances formed by the microorganism (Singh, dkk
2012 : 321).

Iodoform is commonly used in dental practice as an antiseptic either alone,

or in combination with eucalyptus oil or glycerine for the treatment of dry socket,
as a dressing for the large cystic defects and for the soft tissue dressing in the
cases of dehiscence of promote healing by secondary intention (Singh, dkk 2012 :
321).
 Iodine is a mineral that required by the body in relative amounts small, but
has a big role very important for the formation thyroxine hormone. The thyroxine
hormone plays an important role in the metabolism of inside the body. Iodine
deficiency can bad for humans, the consequences, among others, reduced level of
intelligence stunted growth, goiter, endemic cretinism (midget), reduced mental
and psychological abilities, increased prenatal mortality, and delays in physical
development child (slow in lifting head, prone and walking) (Kapantau 2013 : 90).

D. APPARATUS AND CHEMICALS

1. Apparatus
a. Balance sheet ( 1 piece)
b. Watch glass ( 1 piece)
c. Measuring cup 100 ml ( 1 piece)
d. Measuring cup 10 ml ( 2 pieces)
e. Erlenmeyer 500 ml ( 1 piece)
f. Erlenmeyer 250 ml ( 1 piece)
g. Beaker 250 ml ( 1 piece)
h. Funnel ( 1 piece)
i. Spray bottle ( 1 piece)
j. Drop pipette ( 4 pieces)
k. Spatula ( 1 piece)
l. Stopwatch ( 1 piece)
2. Chemicals
a. Pottasium iodide ( KI)
b. Aquadest ( H2O)
c. Acetone (C3H6O)
d. Sodium hypochlorite 20% ( NaOCl)
e. Plain filter paper
E. WORK PROCEDURES
1. Weigh 10 grams of KI, then dissolve it using 100 mL of distilled water
in a 500 mL Erlenmeyer.
2. Add 10 mL of acetone to the KI solution.
 3. Add 75 mL of 20% sodium hypochlorite slowly until the solid iodoform
is no longer formed.
4. Let the solution stand for 10 minutes.
5. Filter the solution using an ordinary funnel equipped with filter paper.
6. Dry the crystals.
7. Put the crystal into the watch glass then weigh it.
F. OBSERVATION RESULT.

nnnNO ACTIVITY RESULT

1. 10 gr KI diluted (colourless) Colorless solution

In 100 mL H2O
2. Add 10 mL acetone Colorless solution

3. Add same of sodium hypochlorik There is colorless become

75 mL and shake cloudy
4. Filtered the solution Colorless to yellow
precipitate solution
5. Dried the crystal Greenish yellow
precipitate
6. Weight the crystal 0,6 gram

G. DATA ANALYSIS

Is known :

Massa KI = 10 gram

Mr KI = 166 gram/mol

Volume aseton = 10 mL

ρAseton = 0,792 g/mL

Mr aseton = 58 g/mol

Massa CHI3 = 0,564 gram

Mr CHI3 = 393,73 g/mol

V NaClO = 20 mL

ρ NaClO = 2,5g/mL

Mr NaClO = 74,5g/mol

NaClO praktek = 0,6 g

Asked : % Rendemen =...?

Penyelesaian:

Massa Aseton = ρ Aseton × V Aseton

= 0,792 g/mL × 10 mL = 7,92 gram

Massa Aseton
Mol Aseton =
Mr Aseton

7,92 gram
= = 0,137 mol
58 gram/mol

Massa KI
Mol KI =
Mr KI

10 gram
=
166 gram/mol

= 0,06 mol

Massa NaClO = ρ NaOCl × V NaClO

= 2,5g/mL × 20 mL = 50 g

Massa NaClO
Mol NaClO =
Mr NaClO
 50 gram
Mol NaOCl = = 5,03 mol
74,5 gram/mol

Adapun reaksinya yaitu :

CH3COCH3 + 3KI + 3 NaOCl CH3COONa + 3 KCl + CHI3 + 2 NaOH

M 0,137 mol 0,06 mol 5,03 mol - - - -

R 0,02 mol 0,06 mol 0,06 mol 0,02 mol 0,06 mol 0,02 mol 0,04 mol

S 0,0117 mol - 4,97 mol 0,02 mol 0,06 mol 0,02 mol 0,04 mol

Massa CHI3 secara teori

Massa CHI3 = mol CHI3 BM CHI3

= 0,02 mol 394 g/mol

= 7,8 gram

=❑
❑  100%
% Rendemen

0 , 6 gram
=  100%
7,8 gram
= 1,28 %

H. PEMBAHASAN
Iodoform (haloform) merupakan senyawa yang dibuat dari reaksi iodin
(halogen) dengan aldehid dan keton dalam suasana basa. Percobaan pembuatan
iodoform dengan tujuan untuk mengetahui prinsip kerja dan teknik-teknik
kristalisasi zat padat organik, mengetahui reaksi haloform dan mengetahui
kegunaan reaksi haloform untuk pembuatan haloform dan asam karboksilat, dan
untuk menunjukkan adanya gugus CH3CO dan CH3CHOH. Prinsip dasar dari
percobaan ini adalah kristalisasi dan rekristalisasi. Kristalisasi dan rekristalisasi
adalah Teknik pemisahan berdasarkan kepolaran suatu zat, perbedaannya adalah
kristalisasi proses pembuatan kristal dari larutannya sedangkan rekristalisasi
adalah proses pemurnian kristal yang sudah ada untuk mendapatkan kristal yang
lebih murni, artinya kristal yang dihasilkan lebih berkualitas dibandingkan
sebelum rekristalisasi. Prinsip kerjanya adalah penimbangan, pelarutan,
pengocokan, penyaringan, pencucian serta pengeringan. Percobaan ini dilakukan
dengan menggunakan kristal KI yang dilarutkan dengan air dan menghasilkan
larutan bening (yang menandakan bahwa KI bersifat Polar dalam aquades). KI
berfungsi untuk membebaskan iod dimana KI yang merupakan penyedia I - akan
menggantikan atom H alfa pada aseton. Penambahan air berfungsi untuk membuat
larutan menjadi homogen atau melarutkan KI secara sempurna. Penambahan air
juga dilakukan karena aseton merupakan suatu zat yang mudah menguap sehingga
dengan penambahan air diharapkan penguapan berkurang atau bila terjadi
penguapan, volume aseton yang diperlukan pada reaksi tidak berkurang.
Kemudian larutan ditambahkan dengan aseton yang berfungsi sebagai bahan pada
pembuatan iodoform (gugus metil keton) dan menghasilkan larutan bening.
Dimana aseton bersifat mudah menguap, jadi pada saat penambahan aseton di
lakukan dengan hati-hati dan tidak dibiarkan di udara bebas dalam waktu lama.
Larutan campuran ditambahkan dengan NaOCl secara perlahan-lahan sambil
dikocok dan menghasilkan larutan dari bening menjadi keruh. Penambahan sedikit
demi sedikit dan sambil dikocok untuk memperoleh hasil yang bagus dari reaksi
akibat dari terjadinya tumbukan antar molekul-molekul yang terdapat dalam
campuran. NaOCl berfungsi untuk membentuk NaOI. Dimana KI bereaksi
dengan NaOCl membentuk KCl dan NaOI. Selanjutnya NaOI ini akan terurai
dalam larutan membentuk NaO+ dan I-. Setelah penambahan aseton, I- akan
bereaksi dengan aseton menghasilkan CH3COCI3 kemudian bereaksi kembali
dengan NaO- dan H dari gugus aseton membentuk CH3CONa yang merupakan
gugus garam karbosilat dan juga membentuk CHI3 yang merupakan iodoform.
Hasil dari perlakuan tersebut yaitu larutan kuning keruh dan didiamkan selama 10
menit. Tujuan dari pendiaman yaitu agar pemisahan antara kristal dengan
larutannya berlangsung baik dan efektif serta endapan yang terbentuk terendapkan
semua.
 Endapan kuning keruh yang diperoleh merupakan iodoform tapi belum
diketahui derajat kemurniannya. Selanjutnya larutan disaring dengan corong biasa
yang dilengkapi dengan kertas saring biasa dan dihasilkan endapan kuning
kehijauan. Penyaringan dilakukan untuk memisahkan kristal yang diperoleh
dengan zat pengotornya dan agar memperoleh kristal iodoform dalam keadaan
murni. Setelah itu endapan di cuci dengan aquades dan dikeringkan di udara.
Tujuan pencucian endapan adalah menghilangkan kontaminasi pada permukaan.
Kristal yang didapat kemudian ditimbang dan di peroleh kristal sebesar 0,6
gram.Kristal iodoform yang diperoleh yakni berwarna kuning, berbentuk serbuk
dan mempunyai bau yang khas yakni bau iodoform itu sendiri. Dimana menurut
teori bentuk dari kristal iodoform yaitu berbentuk serbuk dan berwarna kuning
(Riswiyanto, 2009: 254). Mekanisme reaksi pada pembentukan iodoform yaitu:

NaOCl + KI NaOI+ KCl

O O
CH3 C CH2 I+ NaOI CH3 C CHI2 + NaOH

O O
CH3 C CHI2 + NaOI CH3 C CI3 + NaOH

O O
CH3 C CI3 + NaOH CH3 C NaO + CHI 3

(N a triu m E ta n o a t) ( Io d o fo r m )

Haloform merupakan suatu istilah kumpulan trihalogen turunan metana,

umpama floroform, kloroform, bromoform, iodoform. Istilah umum untuk
menyebut CHX3 adalah “haloform”, maka reaksi ini disebut juga sebagai reaksi
haloform. Iodoform atau disebut juga dengan CHI3 merupakan zat padat hablur
yang berwarna kuning dengan bau khas, yang juga merupakan antiseptik lemah
(Pudjaatmaka, 2002: 291, 333).
I. CONCLUSIONS AND SUGGESTIONS
1. Conclusions
a. Reaksi haloform merupakan reaksi yang menghasilkan senyawa CHX 3
dari metil keton yang mengalami halogenasi.
 b. Prinsip kerja dari kristalisasi yaitu penimbangan, pelarutan, pencucian,
penyaringan dan pengeringan.
2. SUGGESTIONS
For the next practicum, be careful and be more patient when adding
sodium hypochloric to the beaker and while homogenizing it so that the changes
in the precipitated solution containing crystals can be formed properly.
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