According to Organic Chemistry by Jonathan Clayden, Nick Greeves and Stuart Warren (2nd edition), the mechanism for alkene ozonolysis is given as

ozonolysis of alkenes

In Advanced Organic Chemistry, Part B: Reactions and Synthesis, Francis A. Carey and Richard J. Sundberg (5th edition), the ozonolysis of alkene is given as:


But mechanism of ozonolysis of alkynes is not given.

alkyne ozonolysis

What is the correct mechanism of the ozonolysis of alkynes?

  • $\begingroup$ See this: chemistry.stackexchange.com/questions/25190/… $\endgroup$ – Nilay Ghosh Dec 24 '17 at 12:13
  • $\begingroup$ Basically, ozonolysis of alkyne forms different types of compounds, and thus the reaction is too complicated and thus exact mechanism is not completely known. See this: pubs.acs.org/doi/abs/10.1021/ja010166f $\endgroup$ – Nilay Ghosh Dec 24 '17 at 12:17
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    $\begingroup$ Not sure why you removed the italic markup, because that is typically the way book titles are formatted, but I don’t care enough to roll back ;) $\endgroup$ – Jan Dec 24 '17 at 16:51
  • $\begingroup$ As to your 2 examples of alkene ozonolysis, if a hydroxylic solvent is present (MeOH), then the zwitterion is trapped as the methoxy hydroperoxide [R(MeO)C(H)OOH] and it is this species that is reduced. In non-nucleophilic solvent, the ozonide is formed and then reduced. $\endgroup$ – user55119 Dec 24 '17 at 21:12

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