CHEM 2332H Lecture Notes - Benzene, Edda, Sea Otter
15 Jul 2014
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Read nature 2012, 490, 208 and section 17-12b. Friedel-crafts alkylation: this is still sear (electrophilic aromatic substitution) But some problems w/ f-c alkylation: need to have good electrophilic aromatic ring to do this. Can only use benzene, halobenzenes, and activated o/p directing. Meta-directing doesn"t work: just like e1 and sn1, can have carbocation rearrangements -->can complicate product distribution. ->limited in scope for alkyl halide: tough to control rxn b/c products are more reactive than starting materials. Ex: toluene"s 25x faster than benzene --> tert-butyl group can also make rxn a lot faster. Acylation: major contributor b/c filled octets and more bonds. But product can also pick up aluminum trichloride. Won"t get over acylation for f-c acylation, but then alcl3 isn"t as much of a catalyst. Water gets rid of all acids and bases (lewis acids and bases). It"s a competative lewis base that frees products. Going to oxidize zn (its oxidation state is 0 @ beginning --> make zncl2.
