Organic Chemistry Lab - Faculty of Pharmacy - University of Surabaya

Members : Group 5 Class A

1. Ni Putu Ardhiani Kencana Putri (110119227)
2. Dina Qurrotu Aini (110119448)
3. Arif Maulana Azis (110119390)
4. Muhammad Nabiel Aditya Purnomo (110117284)
5. Vincent Chandra K (110119108)
Basic Theories / Abstract

Iodoform (Triiodomethane) is an organoiodine compound with the formula CHI3 and

a tetrahedral molecular geometry. Iodoform is a yellow solid that is relatively
insoluble in water and is chemically reactive in free radical reactions.

Iodoform is used as an antiseptic which is very effective for the skin. It is widely used
before injection. Side effects that arise are brown color and sometimes cause
dermatitis (skin allergy). Almost all pathogenic germs including fungi and viruses are
killed by iodine. So are spores, although it may take longer.

Iodoform can be synthesized based on the halogenation reaction with iodine and
acetone as the base ingredient using sodium hydroxide.

Characteristics of Iodoform include yellow crystals, difficult to dissolve in water,

soluble in alcohol, easily decomposes in the presence of light, melting point 120ºC-
122ºC, molar mass 393.73
Objectives

• Can explain haloform Reaction (Halogenation / Iodization Process)

• Be able to explain the factors that affect the stability of the iodoform formed
Tools & Materials

Tools Materials
• Erlenmeyer Flask • Distilled Water (Aquades)
• Suction Flask • Acetone
• Buchner Funnel • Sodium Hydroxide
• Hotplate • Ethanol
• Suction Pump

• Cork plug

• Oven
 Iodium 10 g

Aseton 12 ml
Aquadem 12 ml

Hasil teoritis 6,4 gram

 Procedure
• Make a short abstract of these directions to use as a guide while doing the work. Make a habit of preparing such abstracts for all experiments.

• Directions. In a 500cc. Florence flask place 10 g of iodine and pour onto this 10 g of acetone. Add in small portions, and with constant shaking, as
much as is needed of a solution made up of 20 cc. Of 8N sodium hydroxide solution and 80 cc of water. If the flask, becomes hot to the hand, cool
it at once with running water. When sufficient sodium hydroxide solution has been added set the flask aside. No free iodine should be present at
this time, nor any suggestion of brown color in the liquid. Look carefully on the bottom of the flask for unattacked iodine.

• After 5 minutes collect the yellow precipitate using the small Buchner funnel. Place filtrate at once in bottle labeled “Iodoform filtrate”. Wash the
solid on the funnel with a little water. The compound is then to be dissolved in the smallest possible quantity of hot ethyl alcohol as follows: put the
iodoform in a small flask arranged for refluxing (see Expt.19). Pour a few cc of alcohol down the condenser (no flames within 6 ft.) and warm on the
electric hot-plate or the steam-bath, shaking the flask at times.

• When the mix is warm add a little more alcohol, then wait till it becomes hot to see whether enough has been added to dissolve all (there will
always be a few shreds of filter paper, etc., which should not be mistaken for iodoform). Do not heat longer than necessary and avoid actual boiling
if possible.

• When enough solvent (about 40 cc) has been added to dissolve all the iodoform at the boiling point of the solution, add about 2 cc additional
solvent, then filter the hot solution through a fluted filter paper, using a funnel previously warmed over the hot-plate or steam-bath.

• Caution- do not inhale the vapor from the solution

 Procedure

• Cover the filtered solution and set aside to cool slowly. In 15 minutes, add about 25 cc of water, meanwhile stirring vigorously to completely
precipitate the iodoform, then filter with the Buchner funnel. Wash the crystals on the funnel with a few drops of cold alcohol (cut off suction during
the washing). Remove the crystals from the filter paper and spread them on a fresh, dry piece of filter paper. The best way to remove paper,etc
from the Buchner funnel is to hold it over a clean filter paper and blow gently through the stem. The end of funnel- stem should first be washed so
that no chemicals can get on the lips. Any crystals remaining in the funnel are removed with knife or spatula. The crystals are to be placed in the
desiccator. Place an identification slip in the desiccator. Products in course of preparation should always be labeled; do not rely on the memory.

• The bottom of the desiccator should contain granules of calcium chloride to a depth of about 15mm. The melting point and weight of the
preparation will be determined after it is dry, at the next laboratory period. For directions for melting point, determinations see Expt.4. Submit the
product in a sample bottle, properly labeled (see Expt.18, p.46).

• During the performance of this experiment the instructor will demonstrate the shape of the iodoform crystals with the microscope. Put a sketch of
the crystals in your report.
Time Table
• Yield, about 55%. Weighing, mixing, filtration 40 min
Crystallization 35 min

M.P determination 20 min

Total 95 min
Work Steps Scheme
Chemical structure
Mechanism Of Reaction
Mechanism Of Reaction
Theoretical Results
References

• Fessenden RJ & Fesenden JS, 1994, Organic Chemistry, 5th edition,

Brooks/Cole Publishing Company Pasific Grove, California, p 574

• Wertheim E, 1948, A Laboratory Guide for Organic Chemistry,

University of Arkansas, 3rd edition, London, p 51-52.

• Wertheim E, 1953, A Laboratory Guide for Organic Chemistry,

University of Arkansas, 3rd edition, London, p 71-72.