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Aldehydes and Ketones

The triiodomethane (iodoform) test

  • 3 things to know
  • Component 2

Overview

Reagents and conditions for the triiodomethane test, positive result of the triiodomethane test and two stages by which the pale yellow solid is produced.

What you need to know

Answer each one before you reveal it.

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Numbers

Calculate the maximum mass of triiodomethane obtainable from 0.0100 mol of ethanal.

Key term

State the reagents and conditions for the triiodomethane test.

Key term

Describe the positive result of the triiodomethane test.

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    State the reagents and conditions for the triiodomethane test.

    Model answer

    Iodine is added to the compound together with aqueous sodium hydroxide, or potassium iodide is used with sodium chlorate(I), and the mixture is warmed gently to about 60 °C.

  2. 2

    Describe the positive result of the triiodomethane test.

    Model answer

    A pale yellow precipitate of triiodomethane, CHI₃, separates out and has a distinctive antiseptic smell.

  3. 3

    Which grouping in a carbonyl compound gives a positive triiodomethane test?

    Model answer

    The CH₃CO— group, so ethanal and any methyl ketone give the precipitate.

  4. 4

    Which grouping other than a carbonyl one gives a positive result, and why?

    Model answer

    The CH₃CH(OH)— group does, because iodine in alkaline solution first oxidises that secondary alcohol to the corresponding methyl ketone, which then reacts in the usual way.

  5. 5

    Ethanol gives a positive triiodomethane test but propan-1-ol does not. Explain the difference.

    Model answer

    Ethanol is oxidised by the reagent to ethanal, which has a methyl group on its carbonyl carbon, whereas propan-1-ol is oxidised to propanal, whose carbonyl carbon carries an ethyl group instead.

  6. 6

    Predict and explain the results of the triiodomethane test on propanal and on propanone.

    Model answer

    Propanone gives the pale yellow precipitate because it is a methyl ketone, while propanal gives none because the carbon next to its carbonyl group is part of an ethyl chain.

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