Type of Transformation Reagents Special Notes -H -X Br2 or Cl2,
Fe weak, small o, p director
I2, CuCl2
-H -R RX, AlX3 moderate o, p director carbocation intermediate
cannot add straight chains to molecule
Only on neutral or activated rings -X -R R2CuLi Only one R group
adds useful for adding
Any alkyl group to an aromatic ring -H -SO3H SO3, H2SO4 meta
director
-SO3H -H H3O+
, heat use as a blocking group
-SO3H -OH NaOH, H2O
-OH -OC(O)CH3 CH3C(O)X, pyridine protected alcohol large strong
o,p director
remove protecting group with NaOH, H2O
-H -NO2 HNO3, H2SO4 meta director
-NO2 -NH2 hydrogenation or strong o, p director
1. Fe or SnCl2, HCl
2. NaOH, H20
-NH2 -NHC(O)CH3 CH3C(O)X, pyridine protected amine large strong
o,p director
remove protecting group with NaOH, H2O
-NH2 -N2+
NaNO2, HCl, H20, 0C or
HNO2, H2SO4, H2O, 0C
-N2+
-H H3PO2
-N2+
-OH H3O+
, > 5C
-N2+
-F HBF4, heat
-N2+
-Cl CuCl
-N2+
-Br CuBr
-N2+
-I NaI or KI
-N2+
-CN CuCN
-CN -CO2H H3O+
-X -CO2H 1. Mg 2. CO2
H - C(O)R (acyl group) RC(O)X, AlX3 meta director Only on
neutral or activated rings
- C(O)R -CH2R hydrogenation Also: Birch reduction and KMnO4
oxidation of benzylic carbons with hydrogens,
