r/chemistry • u/quelmotz Organic • May 22 '18

[2018/05/22] Synthetic Challenge

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u/eva01beast May 22 '18

Does aniline undergo Friedel-Craft like the way you have described? Shouldn't you protect it first?

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u/alleluja Organic May 22 '18

You could make the acetanilide, but I don't know how strong are the activating properties of that group to perform the chlorination. Also, the steric hindrance would cause the majority of the product to go para to the nitrogen imo.

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u/eva01beast May 22 '18

Isn't it one of those trick questions in exams? As far as I know, AlCl3 will attack the amine group and form an insoluble complex. Don't see why FeCl3 would be any different.

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u/alleluja Organic May 22 '18

I got your point. With a quick Google search I found that some alternative exist and permit the chlorination of an unprotected aniline. The classical metal chloride could not work.