Numford
Name reaction

Etard reaction

Toluene is oxidised to benzaldehyde by chromyl chloride in CS2, followed by hydrolysis of the chromium complex.

Class 12, Chapter 8 Aldehydes, Ketones and Carboxylic Acids

  1. TolueneC₆H₅CH₃Arene
  2. Step 1

    (i) CrO₂Cl₂, CS₂ (ii) H₃O⁺

    Etard reaction
    i

    Etard reaction stops at the aldehyde through a chromium complex that hydrolyses.

    OH
    BenzaldehydeC₆H₅CHOAldehyde

Reagents: (i) CrO₂Cl₂, CS₂ (ii) H₃O⁺

Mechanism

How it works

  1. Chromyl chloride forms a brown chromium complex with the methyl group.
  2. The complex does not oxidise further.
  3. Hydrolysis with H₃O⁺ releases benzaldehyde.
Used to prepare

What it makes

Benzaldehyde from toluene.

Limitations

Where it fails

Use chromyl chloride, not KMnO4, otherwise the acid forms.

Which chapter

Class 12, Chapter 8 Aldehydes, Ketones and Carboxylic Acids

Questions

Etard reaction: quick answers

Why does Etard oxidation stop at the aldehyde?

The chromium complex protects the aldehyde until it is hydrolysed.

What does KMnO4 give from toluene?

Benzoic acid.

What is the solvent?

Carbon disulphide.

Plan an organic conversion