Thursday, March 24, 2011

Week 11 of 52: Breaking epoxides with nucleophiles

I think I missed a week and am behind on this. Whatever. I have no sympathy for you. Here is a weird reaction I arbitrarily chose. Learn it.

Epoxides contain a strained ring. It looks like this...
Look at those bond angles. Actually, don't. I mean, I just made that picture in a few seconds. It's not like it's accurate at all. But epoxide rings are strained. They're just waiting to pop open at any second if you give them reason to. Maybe. Actually, I made that up too. You probably shouldn't take this post too seriously. Just so you know.

One way for that ring to open is for a nucleophile to attack one of those α-carbons. Assuming that the reaction takes place in an aqueous environment, this leaves an alkoxide on the α-carbon that was not attacked by the nucleophile, which is protonated by the surrounding water.

The result of this reaction is that each of the carbons from the epoxide now has a different functional group attached to it. One has the nucleophile (whatever that was) and the other has an alcohol. This is probably useful for something. Ugh, sorry. That sounded lame. This isn't working. I need to change the way I do these posts. I need to make them better. This one sucks. I'm so sorry.

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