Answer to Question #87115 in Organic Chemistry for Pankaj chauhan

Question

Explain why addition of water to an alkyne does not give a diol​.

Answer 1

Unlike the additions to double bonds which give alcohol products, addition of water to alkynes gives ketone products ( except for acetylene which yields acetaldehyde. The explanation for this deviation lies in enol-keto tautomerization. The initial product from the addition of water to an alkyne is an enol, and this immediately rearranges to the more stable keto tautomer.

References:

1. Michigan State University [Electronic resource] : Department of Chemistry. - Mode of access: https://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/addyne1.htm. – Date of access: 27.03.2019.