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What is the product of acetylene ($\ce{C2H2}$) and hypochlorous acid ($\ce{HOCl}$) reaction?

I gathered that $\ce{Cl}$ acts as electrophile and so $\ce{HOCH=CHCl}$ is formed. Now two things can happen: it could tautomerize to keto form since enol form is unstable, or another molecule of $\ce{HOCl}$ can add itself, if it adds again there are two ways of adding them, both chlorine atoms could end up on the same carbon or on adjacent carbons. How do we decide what will be the final product?

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  • $\begingroup$ Tautomerization is usually rapid in which case chloroacetaldehyde is formed. If the enol were reacting with more HOCl, the enol would react at the Cl bearing carbon with the electropositive chlorine to afford dichloroacetaldehyde. Depending on the stoichiometry of the reaction, chloroacetaldehyde may re-enolize to give dichloroacetaldehyde. $\endgroup$ – user55119 Sep 12 '18 at 2:29
  • $\begingroup$ Hypochlorous acid is strong oxidant, so resulting products would be various chloroacetic acids, depending on conc. of reagents, temp. etc. $\endgroup$ – Mithoron Sep 12 '18 at 17:05

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