Hydration of internal and terminal alkyne

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When do you use HgSO4 and H2SO4.... and when do you use SiaBH??
The first reaction using HgSO4 is done when water is added to an alkyne in a Markovnikov orientation. This will produce a ketone. If you want to make an aldehyde the method employing a Boron reagent such as Sia2BH is generally employed. This will give the anti-Markovnikov product namely an aldehyde.

Hope this helps,

Dr. Romano
 
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