Question
Question: What will be product in given reaction  which rearranges to form a more stable keto tautomer. The mechanism of the reaction is as follows,
At the first step, the π electron of the triple bond behaves as a Lewis base and attacks the proton, protonating the carbon with hydrogen substituents, and then there is an attack of a nucleophilic water molecule on electrophilic carbocation, this creates an Oxonium ion.
Then the base is deprotonated giving rise to alcohol called enol then occurs tautomerism i.e. concurrent proton and double bond shift, which goes from enol form to keto isomer form.
According to the question prop-1-enyl benzene in the presence of HgSO4 forms 1-phenylprop-1-en-1-ol which on further tautomerization forms propiophenone.
Therefore the correct answer is option C.
Note:
Hydroboration-oxidation method is complementary to the direct Hg2+ catalysed hydration reaction of terminal alkynes because different products are obtained.
Hydration of terminal alkyne with Hg2+ salt and water gives methyl ketone whereas hydroboration-oxidation of the same terminal alkyne gives aldehyde.