Propanal and propanone are both organic compounds containing the carbonyl group. Describe how you could use Tollens' reagent to distinguish between propanal and propanone, and explain the observations you would expect for each compound.

Eduqas A-Level Chemistry — 4.4 Aldehydes and ketones · Describe · 5 marks · View as Markdown

Written & reviewed by James Millett — Biology (Imperial College London), PGCE Science (University of Cambridge).

Model answer (5 marks)

Add a small amount of propanal to a test tube and then add a few drops of Tollens' reagent, followed by gentle warming. The aldehyde group is oxidised to a carboxylic acid, and the silver ions are reduced to metallic silver, giving a bright silver mirror on the inner wall of the tube.

Add a small amount of propanone to a separate test tube and repeat the same procedure. The ketone is not oxidised, so the silver ions remain in solution and no silver precipitate forms; the tube stays colourless.

Thus, a silver mirror indicates the presence of an aldehyde (propanal), while the absence of a mirror indicates a ketone (propanone).

Examiner tips

  • Show the sequence: add compound → add Tollens' reagent → warm gently; mention the silver mirror as key evidence.
  • Explain the redox: aldehyde is oxidised, ketone is not, linking to the observed outcome.

Common mistakes

  • Failing to mention the gentle warming step; the reaction may not proceed at room temperature.
  • Confusing the colour of the solution with the presence of a mirror; the solution remains colourless in both cases but only the aldehyde gives a mirror.

Mark scheme (5 marks)

  1. Tollens' reagent contains silver ions / is a solution of silver nitrate in ammonia / is a silver-containing reagent
  2. Add Tollens' reagent to each compound and warm gently
  3. Propanal (the aldehyde) produces a silver mirror / silver precipitate on the test tube
  4. Propanone (the ketone) does not react / no silver mirror / solution remains colourless
  5. Propanal is oxidised / acts as a reducing agent; aldehydes can be oxidised but ketones cannot

Key terms in this question

carbonyl group · Tollens' reagent

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