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Ozonolysis of Alkynes

ozonolysis of alkynes

Reaction type: Electrophilic Addition

Summary

  • Overall transformation :  C≡C to 2 x CO2H
  • Ozonolysis implies that ozone causes the alkyne to break (-lysis)
  • Reagents : ozone followed by a simple aqueous work-up.
  • If the alkyne is terminal, i.e. contains R≡CH, then the products are RCO2H and CO2 since unstable carbonic acid, HOC(=O)OH, is produced.
  • Note that each of the CC bonds in the C≡C becomes a CO bond

 What would be the products of the ozonolysis reactions of: 
(a) ethyne ? ANSWER
(b) 1-butyne ? ANSWER
(c) 2-butyne ? ANSWER
(d) cyclooctyne ? ANSWER

Related Reactions

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organic chemistry © Dr. Ian Hunt, Department of Chemistry University of Calgary