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Aldehydes and Ketones

Reaction with 2,4-dinitrophenylhydrazine

  • 3 things to know
  • Component 2

Overview

Words what happens to the two molecules during this reaction, class name of the solid product of this reaction and why the product of this reaction is strongly coloured.

What you need to know

Answer each one before you reveal it.

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Key term

Describe in words what happens to the two molecules when 2,4-dinitrophenylhydrazine reacts with a carbonyl compound

Key term

What is Brady's reagent made from?

Key term

State the positive result seen when Brady's reagent is added to a suitable compound.

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    What is Brady's reagent made from?

    Model answer

    It is a solution of 2,4-dinitrophenylhydrazine in methanol acidified with concentrated sulfuric acid.

  2. 2

    State the positive result seen when Brady's reagent is added to a suitable compound.

    Model answer

    A precipitate forms at once, ranging in colour from yellow through orange to red.

  3. 3

    Which functional group does Brady's reagent detect, and what can a positive result not tell you?

    Model answer

    It detects the carbonyl group, C=O, of an aldehyde or a ketone, but a positive result does not reveal which of the two classes is present.

  4. 4

    Carboxylic acids and esters also contain a carbon–oxygen double bond. Why do they give no precipitate?

    Model answer

    In those compounds the carbonyl carbon also carries an oxygen atom whose lone pairs are delocalised onto it, which reduces the δ+ charge so the reagent's nitrogen cannot add to it.

  5. 5

    Name the type of mechanism by which 2,4-dinitrophenylhydrazine reacts with a carbonyl compound.

    Model answer

    Nucleophilic addition–elimination, which is also called a condensation reaction.

  6. 6

    Describe in words what happens to the two molecules during this reaction.

    Model answer

    The nitrogen of the —NH₂ group attacks the δ+ carbonyl carbon and adds to it, and a molecule of water is then eliminated, so the carbon–oxygen double bond is replaced by a carbon–nitrogen double bond joining the two parts together.

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