Name: Sanglad, Chariezza Lei J.

Date Performed: September 19, 2017

Regala, Erlindo

Ramos, Melanie

Group No:5 Date Submitted: October 10, 2017

Experiment no:7

SYNTHESIS OF IODOFORM
Objectives:
1. To be able to synthesize iodoform using solid iodine and sodium hydroxide as starting
material to convert a ketone like acetone to Iodoform.
2. To be able to measure the synthesized Aspirin’s percent yield.
3. To determine the melting point of acetanilide and to compare the experimental melting
point to the true value.

About the Product:

Iodoform is the organoiodine compound with the formula CHI3. A pale yellow,
crystalline, volatile substance, it has a penetrating and distinctive odor (the smell is sometimes
referred to as the smell of hospitals, where the compound is still commonly used) and, analogous
to chloroform. It is occasionally used as a disinfectant. It is also known as tri-iodomethane, carbon
triiodide, and methyl triiodide. It is used as a mild antiseptic and disinfectant. It is also used in the
preparation of many medicinal ointments used as pain-relievers.

Procedure:
sodium hydroxide in 4 ml of water in a 100 ml Erlenmeyer flask.
0.7 mL of acetone
1 g powdered iodine,
water bath at 70 -80 C(15 mins).
cooled, (yellow crystals)
Filter the solution,
wash the iodoform with water and recrystallize from alcohol
dry the iodoform crystals.
Data and Results:

Table 1. Synthesis of Iodoform

Mass of iodine (g) 1.0131
Volume of acetone (mL) 0.7
Mass of sodium hydroxide (g) 1.0112
Mass of watch glass (g) 42.0035
Mass of watch glass, aspirin and filter paper 43.6233
(g)

Mass of filter paper (g) 0.7306

Mass of iodoform (actual yield) (g) 0.8892
Theoretical yield (g) 1.5748
Percent yield of iodoform (%) 56.46%

Table 2. Melting Point of Iodoform

Experimental Melting Point (°C) 120

Theoretical Melting Point (°C) 119-121

Discussion:

In this method we will be converting a ketone like acetone to Iodoform using solid iodine
and sodium hydroxide. The chemical reaction can be represented as shown below.

Iodine solution is added to a small amount of an alcohol, followed by just enough sodium
hydroxide solution to remove the color of the iodine. If nothing happens in the cold, it may be
necessary to warm the mixture very gently. A positive result is the appearance of a very pale yellow
precipitate of triiodomethane (previously known as iodoform): CHI3, which apart from its color,
can also be recognized by its faintly "medical" smell.

In the first step, the halogen disproportionates in the presence of hydroxide to give the
halide and hypohalite. If a secondary alcohol is present, it is oxidized to a ketone by the hypohalite.
If a methyl ketone is present, it reacts with the hypohalite in a three-step process. Under basic
conditions, the ketone undergoes keto-enol tautomerization. The enolate undergoes electrophilic
attack by the hypohalite (containing a halogen with a formal +1 charge). Then the α position has
been exhaustively halogenated, the molecule undergoes a nucleophilic acyl substitution by
hydroxide, with −CX3 being the leaving group stabilized by three electron-withdrawing groups. In
the third step the −CX3 anion abstracts a proton from either the solvent or the carboxylic acid
formed in the previous step, and forms the haloform. At least in some cases (chloral hydrate) the
reaction may stop and the intermediate product isolated if conditions are acidic and hypohalite is
used.

This reaction forms the basis of the iodoform test which was commonly used in history as
a chemical test to determine the presence of a methyl ketone, or a secondary alcohol oxidizable to
a methyl ketone. When iodine and sodium hydroxide are used as the reagents a positive reaction
gives iodoform, which is a solid at room temperature and tends to precipitate out of solution
causing a distinctive cloudiness. In organic chemistry, this reaction may be used to convert a
terminal methyl ketone into the analogous carboxylic acid.
Crystals obtained was recrystallized and iodoform crystals were reviewed from its color
and smell as well as its melting point. The theoretical melting point of iodoform is 119°C-122°C.
In the experiment, the observed melting point was 120°C. The iodoform crystals were weighed
and found out to be 0.8892 g and the percent yield was 56.46%.
Reaction Mecahanism:
Calculations:

• Moles acetone (C3H6O); density acetone= 0.791g/ml; MW=58.08 g/mol

0.791𝑔
0.7ml𝑥 =0.5537 g
𝑚𝑙

1 𝑚𝑜𝑙 𝑎𝑐𝑒𝑡𝑜𝑛𝑒
0.5537g C3H6O𝑥 58.08 𝑔 𝑎𝑐𝑒𝑡𝑜𝑛𝑒=0.0095 mol acetone

• Moles sodium hydroxide (NaOH); MW= 39.997 g/mol

1 𝑚𝑜𝑙 𝑁𝑎𝑂𝐻
1.0112 g NaOH 𝑥 39.997 𝑔 𝑁𝑎𝑂𝐻 = 0.02533 𝑚𝑜𝑙 𝑁𝑎𝑂𝐻

• Moles iodine (I2); MW= 253.809 g/mol (LIMITING REAGENT) 1:1

1 𝑚𝑜𝑙 𝐼𝑜𝑑𝑖𝑛𝑒
1.0131 g I2 𝑥 0.0040 𝑔 𝑖𝑜𝑑𝑖𝑛𝑒
253.809 𝑔

• Moles of a molecule = (Mass of substance) / (Molar mass)

Therefore,
Mass of a substance = (Moles of a substance) x (Molar mass)

• Mass of a substance = (0.0040 mol )x (393.7 g/mol )

= 1.57480 g iodoform

• The percentage yield for this synthesis of iodoform may be calculated as follows:
Theoretical yield = 1.5748 g
Actual yield =0.8892g
Actual yield
• Percentage yield = x 100%
𝑀𝑎𝑥𝑖𝑚𝑢𝑚 𝑌𝑖𝑒𝑙𝑑
0.8892
= x 100%
1.5748
=56.46%