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Aldehydes and Ketones

2,4-dinitrophenylhydrazine and the identification of carbonyls

  • 3 things to know
  • Unit A2 1

Overview

Recall questions on the orange precipitate and what it proves, the equations for ethanal and propanone, the small molecule eliminated and the addition–elimination mechanism, why an ester gives no precipitate, purifying the derivative and using its melting point, what a broad range indicates, and why the test cannot separate aldehyde from ketone.

What you need to know

Answer each one before you reveal it.

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Key term

State what is observed when 2,4-dinitrophenylhydrazine solution is added to a ketone.

Key term

Name the class of product formed when a carbonyl compound reacts with 2,4-dinitrophenylhydrazine.

Key term

Write the equation for the reaction of ethanal with 2,4-dinitrophenylhydrazine.

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    State what is observed when 2,4-dinitrophenylhydrazine solution is added to a ketone.

    Model answer

    An orange crystalline precipitate forms immediately.

  2. 2

    State what the formation of that precipitate tells you about the compound tested.

    Model answer

    It shows that the compound contains a carbonyl group as an aldehyde or a ketone.

  3. 3

    Name the class of product formed when a carbonyl compound reacts with 2,4-dinitrophenylhydrazine.

    Model answer

    The product is a 2,4-dinitrophenylhydrazone.

  4. 4

    Write the equation for the reaction of ethanal with 2,4-dinitrophenylhydrazine.

    Model answer

    The equation is CH₃CHO + H₂NNHC₆H₃(NO₂)₂ → CH₃CH=NNHC₆H₃(NO₂)₂ + H₂O.

  5. 5

    Write the equation for the reaction of propanone with 2,4-dinitrophenylhydrazine.

    Model answer

    The equation is CH₃COCH₃ + H₂NNHC₆H₃(NO₂)₂ → (CH₃)₂C=NNHC₆H₃(NO₂)₂ + H₂O.

  6. 6

    Name the small molecule eliminated in the reaction with 2,4-dinitrophenylhydrazine.

    Model answer

    A molecule of water is eliminated.

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