Science - Chemistry - Organic Chemistry - 4 Alcohols (P7172000)

4.5 The iodoform test

Experiment by: Anouch
Printed: Feb 25, 2014 1:51:07 PM
interTESS (Version 13.12 B214, Export 2000)

Task

Task
How can methanol be distinguished from ethanol? (2)
Carry out the iodoform test with methanol and ethanol.

Use the space below for your own notes.

Logged in as a teacher you will find a button below for additional information.

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Addtional Information
Learning objectives
• The two substances can be distinguished from each other by the fact that ethanol
in contrast to methanol reacts with alkaline iodine/potassium iodide solution
forming a yellow precipitate.
• The yellow precipitate consists of triiodomethane, which can be shown to be a
halogenated alkane by the Beilstein test.

Notes on setup and procedure

Preparation:
Iodine/potassium iodide solution can also be freshly prepared (20 g Kl and 10 g I2 in
100 ml distilled water).
Prepare dilute caustic soda (12 g NaOH to 100 ml water). The concentrations need
not be exact. Cut out copper strips for the experiment or use some which were left
over in previous experiments.

Hazard and precautionary statements

Ethanol:
H225:Highly flammable liquid and vapour.
P210: Keep away from heat/sparks/open flames/hot surfaces – No smoking.

Methanol:
H225: Highly flammable liquid and vapour.
H301: Toxic if swallowed.
H311: Toxic in contact with skin.
H331: Toxic if inhaled.
H370: Causes damage to organs.
P210: Keep away from heat/sparks/open flames/hot surfaces – No smoking.
P233: Keep container tightly closed.
P280: Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: Wash with soap and water.
P309+P310:IF exposed or you feel unwell: Immediately call a POISON CENTER or
doctor/physician.

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Sodium hydroxide:
H314: Causes severe skin burns and eye damage.
H290: May be corrosive to metals.
P280: Wear protective gloves/protective clothing/eye protection/face
protection.
P301+P330+P331:IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P309+P310: IF exposed or you feel unwell: Immediately call a POISON CENTER
or doctor/physician.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses if present and easy to do – continue rinsing.

Hazards
• Ethanol and methanol are highly inflammable. Extinguish all open flames while
handling them!
• Wear protective glasses!
• Methanol is poisonous. Carry out the experiment in the fume hood if possible
and air the room well! Wash splashes on the skin off with copious water!
• Sodium hydroxide solution is corrosive. Solutions of iodine/potassium iodide in
water attack the skin. Do not allow either of them to contact skin!

Notes
Iodine reacts in alkaline solution with methylene groups which contain a neighbouring
hydroxyl or carbonyl group under the formation of triiodoalkanes. By the reaction
with ethanol, one of the products is triiodomethane (iodoform), which precipitates
out as a yellow solid:

CH3CH2OH + 4 I2 + 6 NaOH → CHI3 + HCOONa + 5 NaI + 5 H2O

As methanol does not contain such groups, it cannot react to triiodomethane under
the given conditions.

Remarks on the method

The differences between methanol and ethanol will be carried over to the experiment
with longer-chain alcohols which follow (P7172100), so that the homologous series
of the alkanes can be derived from the experimental data.

Advanced courses: The iodoform reaction can be used as an example for the discussion
of aliphatic electrophilic substitution reactions.

Waste disposal
• Pour solutions into the waste container for combustible organic liquids.
• Put filters and residues into the container for solid organic waste.

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 Material

Material
Material from "TESS advanced Chemistry Set Organic Chemistry, CH-4 " (Order
No. 15304-88)

Position No. Material Order No. Quantity

1 Test tube rack for 12 tubes, holes d = 22 mm, wood 37686-10 1
2 Test tube, 180x18 mm 37658-10 (2)
3 Test tube brush w. wool tip, d = 25 mm 38762-00 1
4 Test tube holder, up to d = 22 mm 38823-00 1
5 Lab. pencil, waterproof 38711-00 1
6 Graduated cylinder, 10 ml, plastic 36636-00 1
7 Funnel, plastic, dia. 50 mm 36890-00 1
8 Protecting glasses, clear glass 39316-00 1
9 Spoon spatula, special steel 33398-00 1
10 Pipette with rubber bulb 64701-00 2
11 Glass beaker DURAN®, short, 250 ml 36013-00 1

Chemicals, Additional Material

Position No. Material Order No. Quantity

Bunsen burner /DIN/, nat.g., w. cock 32168-05 1
Safety gas tubing, DVGW, sold per metre 39281-10 1
Ethanol, extra pure ab. 95%, 1000 ml 30008-70

Aqueous potassium iodide/ iodine solution (Lugol's 30094-25

solution), 250 ml
Copper foil, 100 g 30117-10

Methanol tech. gr., 1000 ml 30142-70

Sodium hydroxide, flakes, 1000 g 30157-70

Circular filter, d = 90 mm, 100 pcs 32977-03

Hot water

Material required for the experiment

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 Action

Action
Hazards
• Ethanol and methanol are highly inflammable. Extinguish all open flames while handling
them!
• Wear protective glasses!
• Methanol is poisonous. Carry out the experiment in the fume hood if possible and air the
room well! Wash splashes on the skin off with copious water!
• Sodium hydroxide solution is corrosive. Solutions of iodine/potassium iodide in water
attack the skin. Do not allow either of them to contact skin!

Procedure
Number the test tubes from 1 to 2 (Fig. 1). Put 1 ml of methanol in the first test tube, 1 ml of
ethanol in the second one (Fig. 2).

Fig. 1 Fig. 2

Add 2 ml of dilute sodium hydroxide solution to each of the alcohols in the test tubes. Carefully
shake the tubes until the liquids are completely mixed. Add the solution of iodine in aqueous
potassium iodide dropwise (Fig. 3) until each liquid has a weakly brown colour (Fig. 4).

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 Fig. 3 Fig. 4

Half-fill the beaker with hot water and place the test tubes in it (Fig. 5). Wait about 5 minutes,
then put the test tubes next to each other in the test tube rack.

Fig. 5

When they have cooled down, filter the content of test tube 2 into the emptied beaker (Fig. 6).
Scratch some of the residue from the filter, put it on a strip of copper foil and carry out the
Beilstein test (Fig. 7). Remove the test tubes containing alcoholic solutions before lighting the
Bunsen burner).

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 Fig. 6 Fig. 7

Waste disposal
• Pour solutions into the waste container for combustible organic liquids.
• Put filters into the container for solid organic waste.

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 Results

Results
Note the observations you make.

Test tube 1:

Test tube 2:

Test tube 1:
The brown-coloured methanol solution does not change.
Test tube 2:
A sweet-smelling, yellow precipitate forms in the ethanol solution after a short time.

State the results of the Beilstein test.

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When the residue from the filter is heated on the copper strip, it colours the flame
green.

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 Evaluation

Evaluation
Question 1:
Draw conclusions from your observations.

In contrast to methanol, ethanol reacts with alkaline iodine/potassium iodide solution

forming a yellow precipitate whose sweet smell suggests that it is a halogenated
alkane. This is confirmed by the positive result of the Beilstein test. Methanol and
ethanol can therefore be distinguished from each other by the iodoform test.

Question 2:
Enter the properties of methanol and ethanol which have been observed in previous experiments
in the "General data sheet", look up missing entries in your text book to fill it completely.

See "General data sheet"

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 General data sheet

General data sheet

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Name of Methanol
the
substance:
Chemical nnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnn
formula:
Colour: nnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnn
State of nnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnn
aggregation:
Melting nnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnn
point:
Boiling point: nnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnn
Other
properties:

Occurrence/
preparation:

Use:

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Name of the substance:Methanol

Chemical formula: CH3OH

Colour: colourless

State of aggregation: liquid

Melting point: -97 °C

Boiling point: 64.7 °C

Other properties: very poisonous, causes blindness;

combustible; borax test: positive (green flame);
iodoform test: negative

Occurrence/ dry distillation of wood ("wood spirit");

preparation: catalytically from carbon monoxide;
evolved during fermentation

Use: solvent, fuel

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Name of Ethanol
the
substance:
Chemical nnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnn
formula:
Colour: nnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnn
State of nnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnn
aggregation:
Melting nnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnn
point:
Boiling point: nnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnn

Other
properties:

Occurence/
preparation:

Use:

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Name of the substance:Ethanol

Chemical formula: C2H5OH

Colour: colourless

State of aggregation: liquid

Melting point: -114 °C

Boiling point: 78.3 °C

Other properties: poisonous in large quantities;

combustible; borax test: negative;
iodoform test: positive (yellow precipitate)

Occurrence/ alcoholic fermentation

preparation:

Use: in alcoholic beverages; solvent, fuel

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