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Question

State true or false: acetylene on ozonolysis gives glyoxal.


A
True
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B
False
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Solution

The correct option is A True

Explanation for the correct option

Ozonolysis

  • Ozonolysis is the reaction in which an alkene reacts with ozone in an inert solvent (ether, CCl4 etc.), to form an explosive and unstable ozonide.
  • Ethylene reacts with ozone to produce acetylene ozonide which is further hydrolyzed in the presence of zinc to form glyoxal.
  • The reaction is given as: CHCHacetyline+O3ozoneozonoideZn-H2OOHC-CHOglyoxal
  • Mechanism of the reaction:
    • Step 1: Initial electrophilic addition of ozone to the carbon-carbon triple bond.

  • This forms the molozonide intermediate.
  • It is an unstable intermediate and continues further with the reaction
  • It undergoes fragmentation to form a molecule with a carbonyl group and a carbonyl oxide group.
  • Step 2: The carbonyl and the carbonyl oxide rearrange themselves and form a stable ozonide intermediate.

  • The ozonide intermediate undergoes a reductive workup using zinc in water.
  • A reducing agent is added that decomposes the ozonide into glyoxal.

ozonoideZn-H2OOHC-CHOglyoxal

Hence the given statement is true.


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