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  4. The major product of the addition of water molecule to propyne in the presence of mercuric sulphate and dilute sulphuric acid is

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Q. The major product of the addition of water molecule to propyne in the presence of mercuric sulphate and dilute sulphuric acid is

MGIMS WardhaMGIMS Wardha 2014

Solution:

In the presence of $ {{H}_{2}}S{{O}_{4}} $ and $ HgS{{O}_{4}} $ as a catalyst, $ {{H}_{2}}O $ adds to triple bond of propyne to form an unstable enol which readily tautomenses to the propanone. Addition occurs according to Markownikoff s rule. $ C{{H}_{3}}-C\equiv CH+{{H}^{+\delta }}-O{{H}^{-\delta }}\xrightarrow[{}]{HgS{{O}_{4}},{{H}_{2}}S{{O}_{4}}} $ $ \underset{Enol\,(unstable)}{\mathop{\left[ C{{H}_{3}}-\overset{\begin{smallmatrix} OH \\ | \end{smallmatrix}}{\mathop{C}}\,=\overset{\begin{smallmatrix} H \\ | \end{smallmatrix}}{\mathop{CH}}\, \right]}}\,\xrightarrow[{}]{{}}\underset{\Pr opanone}{\mathop{C{{H}_{3}}-\overset{\begin{smallmatrix} O \\ || \end{smallmatrix}}{\mathop{C}}\,=C{{H}_{3}}}}\, $