Monday, September 26, 2011

Week 24 of 52: Addition of water to alkynes

Last week's post show's how water adds across an alkene. An alkyne has the same kind of bond that an alkene does (alongside another bond, but more on that later or possibly never). So the reaction is similar for alkynes. However, the product of this reaction can potentially be something completely different (an alkene just becomes an alcohol).

My book points out that either a strong acid or a mercuric catalyst (I could explain what that means, but I don't feel like it) can facilitate a reaction in which water adds across one of the bonds, leaving a double bond and an alcohol on the same carbon. This is called an enol.
It's a hideous portmanteau of "alkene" and "alcohol." But nevermind that. What's important is that this sort of thing is unstable. So it does something super-cool. I am not kidding. This is tautomerization, and it's awesome.
The enol form of the molecule tautomerizes into the "keto" form (which could be either a ketone or an aldehyde). I won't spend any more time on tautomerization right now, despite how freaking cool it is.

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