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Question
How is the iodoform test carried out?
Very Long Answer
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Solution
The iodoform test is performed by reacting a suspected compound with iodine in a basic solution, typically with sodium hydroxide. A positive result is the formation of a pale yellow precipitate of iodoform, accompanied by a characteristic antiseptic odor.
Principle of the test: The iodoform test, or haloform reaction, is used to detect the presence of one of two functional groups:
- Methyl ketones: Compounds containing a methyl group directly attached to a carbonyl group.
- Secondary alcohols: Compounds containing a methyl group and a hydroxyl group on the same carbon. Ethanol is the only primary alcohol that gives a positive result.
Compounds with these structures are first oxidized (if an alcohol), and then undergo exhaustive iodination followed by cleavage to produce iodoform.
Procedure: There are two common variations for carrying out the iodoform test in a laboratory setting.
- Using iodine and sodium hydroxide:
- Prepare the sample: Place a small amount of the compound to be tested (a few drops of liquid or a few milligrams of solid) into a clean test tube.
- Add reagents: Add a few millilitres of iodine-potassium iodide (KI-I2) solution to the test tube. Next, add a 10% sodium hydroxide (NaOH) solution dropwise until the solution's dark brown color disappears or becomes very pale yellow.
- Observe the reaction: If no precipitate forms at room temperature after 2-3 minutes, gently warm the test tube to about 60°C. If the brown color returns, add a few more drops of NaOH.
- Confirm the result: The appearance of a pale yellow precipitate of iodoform (CHI3) after heating and standing confirms a positive test.
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Using potassium iodide and sodium hypochlorite:
- Prepare the sample: Place about 0.2 mL of the test compound in a test tube.
- Add reagents: Add 10 mL of 10% aqueous potassium iodide.
- Warm and observe: Gently warm the test tube for a few minutes. The formation of yellow iodoform crystals indicates a positive result.
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Chapter 10: Haloalkanes and Haloarenes - REVIEW EXERCISES [Page 593]
