Saturday, July 9, 2011

Week 17 of 52: Alkyne synthesis by two successive dehydrohalogenations

I've already covered the E2 mechanism by which an alkyl halide can be converted to an alkene. With a particularly strong base, a dihalide like the one shown in the previous post can undergo an E2 reaction twice, yielding an alkyne.
Like that! Or something. Note the use of sodium amide. I put it there because this reaction requires a very strong base. There's an explanation for this, but having just read over it, I find it beyond the scope of what I'm doing here (I definitely haven't introduced the concepts needed to understand it). So we'll just leave it at that. This reaction requires a very strong base.

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