Anti-Markovnikov addition (Syn addition) followed by enol/keto tautomerization
EAS Nitration: aromatic ! nitro-aromatic NO2
HNO3 H2SO4
EAS Halogenation: aromatic ! halo-aromatic X
X2 FeX3 (X= Cl, Br, I)
Friedel-Crafts Alkylation: aromatic ! alkyl-aromatic R R R + others R
R-Cl AlCl3
H2SO4
R + others
Friedel-Crafts Acylation: aromatic ! acyl-aromatic O O R
Cl
R
AlCl3 EAS Sulfonation: aromatic ! aromatic sulfonic acid SO3H
SO3 H2SO4 Benzylic/allylic bromination O CH3
N Br
Br
O NBS
CH2
Benzylic oxidation: alkyl-aromatic ! aromatic carboxylic acid O R
KMnO4
OH
Nucleophilic aromatic substitution: aryl halide ! aryl-nucleophile Note: at least X Nucleophile Nu one activating group in ortho or para position is necessry A A