What is cleaving?

Alkenes, which contain a C=C double bond, can be oxidized using acidified potassium manganate(VII) solution. Depending on the reaction conditions, the C=C double bond can be either broken completely or converted to diols. 

Oxidation under hot concentrated KMnO4/H+

  • The C=C double bond in the alkene breaks down entirely. The products that form depend on what is bonded to the carbon atoms in the C=C double bond.
  • If a carbon atom is bonded to two hydrogen atoms, it oxidises to form a CO2 molecule.
    \( \text{H}_2\text{C}=\text{CH}_2 + 6[\text{O}] \rightarrow \text{CO}_2 + \text{CO}_2 + 2\text{H}_2\text{O} \)
  • If a carbon atom is bonded to one hydrogen atom and one alkyl group, it oxidises to form a CO (aldehyde) group first, which oxidises again to form a COOH (carboxylic acid) group.
    \( \text{RHC} = \text{CHR} + 2[O]\rightarrow \text{RCHO} + \text{RCHO} + 2[O]\rightarrow \text{RCOOH} + \text{RCOOH} \)
  • If a carbon atom is bonded to two alkyl groups, it oxidises to form a C=O (ketone) group.
    \( R_1 R_2 C = C R_3 R_4 + 2[O]\rightarrow R_1 (CO) R_2 + R_3 (CO) R_4 \)
  • To obtain aldehydes, the solution must be heated with a distillation apparatus. This is done to collect the aldehyde vapour before it oxidises again to form carboxylic acids.
  • To obtain other oxidised substances, the solution must be heated under reflux. 
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Oxidising under cold dilute KMnO4

  • Under cold dilute conditions, the C=C bond is not fully broken. Instead, -OH groups are attached to the two carbon atoms, forming diols
  • The diols can be oxidised again to form carboxylic acids, ketones or CO2 depending on the chemical structure of the compound.
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