Water adds to alkyne when alkyne is treated with 40% H2SO4 containing 1% HgSO4 (as a catalyst) to form a carbonyl compound. The addition of water follows. Markownikoff’s rule forming enol as intermediate, which tautomerizes to give a more stable carbonyl compound. For example, acetylene gas when passed through dil. H2SO4 containing HgSO4 initially forms vinyl alcohol, which tautomerizes to acetaldehyde.
The reaction is believed to take place via the formation of a three membered ring involving H2O ion.
Acetylene is the only alkyne forming an aldehyde in this reaction. Higher homologues of acetylene either form a single ketone or a mixture of ketones. For example, 2-pentyne gives a mixture of 2-pentanone and 3-pentanone.
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