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EAS E
E Ortho/Para-Substitution Meta-Substitution E
Recall that protonation of an alkene occurs such that the more stable carbocation is generated. Similarly, regioselectivity in EAS reactions are directed by the relative stabilities of the carbocationic intermediates.
H R
Cl
Note that para-attack of the electrophile generates a more stable carbocationic intermediate than meta-attack. For this reason, para-attack is favored.
Note that para-attack of the electrophile generates a more stable carbocationic intermediate than meta-attack. For this reason, para-attack is favored.
Note: The methoxy and methyl groups are cation-stabilizing groups. In general, cationstabilizing groups are ortho/para-directors.
Professor M. J. Krische, UT Austin
Note: The nitro- and ester groups are cation-destabilizing groups. In general, cation-destabilizing groups are meta-directors.
Professor M. J. Krische, UT Austin
In general:
All activating groups are Ortho/Para-Directors and are electrondonating. All deactivating groups are Meta-Directors and are electronwithdrawing. Any group with a lone pair of electrons adjacent to the ring is an Ortho/Para-Director
Professor M. J. Krische, UT Austin