《有机化学精品教学》（汕头大学）Chap.04 Aromatic hydrocarbon（2012）.pptVIP

Ω= = 4 2×8 + 2－10 2 A: C8H10 Ω= = 6 2×8 + 2－6 2 B: C8H6O4 B one product HNO3/ H2SO4 Exercise page 84. 1. (3) (7) (8) 2. 4.(2) 6. 7. 8. HNO3 / H2SO4 benzoicacid HNO3 / H2SO4 + toluene Locating effect of the electrophilic substitution ortho/para locating groups: The groups on the bebzene ring are most effective at directing further substitution to the ortho and para position, such as: O O –NH2, –HNR, –HN–C–R, –OH, –OR, –O–C–R, –X,– R stronger locating effect weaker In these groups, the atoms connecting directly with the benzene ring do not contain unsaturated bonds, most of them have lone pair electrons or negative chages. ortho/para locating effect E+ directs here o/p E E + o/p o/p o/p directs here o/p electrophilic Cl2 , h? Although the same start material and same reagent, but different reaction condition give you different product. meta locating groups: The groups on the benzene ring are most effective at directing further substitu-tion to the meta position, such as: In these groups, the atom connecting directly with the benzene ring, contains unsaturated bonds or positive charges. O –NR3 , –NO2 , –CN , –SO3H , –CHO , –C–R , + –COOH , –COOR m directs here m m E E+ meta locating effect How locating effect work? δ δ δ δ δ Something More: If there are two ortho/para directors on the benzene ring, the stronger one will direct the next substitution. If there is one ortho/para director and one meta director one the benzene ring, the ortho/para director is the directing group. Two meta groups on benzene ring will cause the electron density of benzene reduce too much, so the next electrophilic