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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: kaslee on March 11, 2019, 03:47:24 AM

Title: question regarding a friedel-crafts alkylation w/ tert-butyl chloride and phenol
Post by: kaslee on March 11, 2019, 03:47:24 AM

i am writing up a report for this experiment wherein we synthesized p-tert-butylphenol via a friedel-crafts reaction. i'm just a bit stuck on why the para-substituent is observed? i drew out resonance structures for the ortho meta and para positions and noticed that the para and ortho positions had greater number resonance structures.

but why is it that, at least for my product, only the para- position was observed, and not the ortho? could it be due to the steric bulk of the tert-butyl group or no?

Title: Re: question regarding a friedel-crafts alkylation w/ tert-butyl chloride and phenol
Post by: spirochete on March 11, 2019, 03:34:15 PM

Yes, that's the reason.