Addition of water to an alkyne gives a keto-enol tautomer product. What will be the enol that is in equilibrium with the given ketone 2-Pentanone?

1 Answer
Jul 8, 2016

Since the parent ketone is unsymmetric, two enol products are possible.


#H_3"C"C(=O)CH_2CH_2CH_3 rightleftharpoonsH_3C(HO)C=CHCH_2CH_3+H_2C=C(OH)CH_2CH_2CH_3#

What do you think would happen to the enol hydrogens if the parent ketone were involved in an equilibrium with #D^(+)"/"D_2O" "(D=""^2H)#? Could deuterium be incorporated on the backbone of the ketone?