CHE 332 Chapter Notes - Chapter 15: Aluminium Chloride, Acyl Group, Carbocation
Document Summary
Chapter 15: reactions of aromatic compounds notes: electrophilic aromatic substitution. Step 1 is slow, step 2 is fast (regaining aromaticity: halogenation, aluminum chloride (alcl3) and iron chloride (fecl3) for chlorination, mechanism: In concentrated sulfuric acid, sulfur trioxide is produced in an equilibrium in which. In most friedel crafts acylations the electrophile appears to be an acylium ion formed from an acyl halide: Ewg, so meta makes the best of a bad situation. It is the least unfavorable of three unfavorable pathways. The oxidizing agent requires a benzylic hydrogen, which is why tert- Amino groups and hydroxyl groups not only activate the ring toward electrophilic substitution but also activate it toward oxidation. If (cid:455)ou"re tr(cid:455)i(cid:374)g to prepare ortho- or para-nitroaniline, nitration of aniline destroys the (cid:271)e(cid:374)ze(cid:374)e ri(cid:374)g (cid:271)e(cid:272)ause it is o(cid:454)idized (cid:271)(cid:455) the (cid:374)itri(cid:272) a(cid:272)id. So (cid:455)ou (cid:272)a(cid:374)"t do a dire(cid:272)t nitration of aniline. For ortho directing, convert and then use sulfonation instead of nitration.
