ORGANIC CHEMISTRY 3540

ELECTROPHILIC AROMATIC SUBSTITUTION

EXAMPLES

SPECIFIC MECHANISMS

GENERAL MECHANISM

ELECTROPHILIC AROMATIC SUBSTITUTION

EXAMPLES

MECHANISM CONSIDERATIONS

BROMINATION

CHLORINE HAS THE SAME MECHANISM

FLUORINE - TOO REACTIVE!

IODINE - TOO INACTIVE

NITRATION

NITROBENZENE (C₆H₅NO₂) CAN BE REDUCED TO ANILINE (C₆H₅NH₂) USING 1) SnCl₂ AND HCl FOLLOWED BY 2) OH^-1.

SULFONATION

FRIEDEL-CRAFTS ALKYLATION

PROBLEMS:

RCl ONLY ALKYL HALIDE (NOT ARYL OR VINYL).
NOT ALL AROMATICS CAN BE ALKYLATED.
POLYALKYLATION.
REARRANGEMENTS

ACYLATION