Monosubstituted Benzenes IR
690 -710, 730 - 770
Ortho Sub Benzene
735-770
Meta Sub Benzene
690-710, 750-810
Para Sub Benzene
790-840
Halogenation of benzene
Br2 + Febr3 -- > Br-Benzene, HBr, FeBr3
Nitration of Benzene
HNO3 + H2SO4 -- > NO2-Benzene, H2SO4
Sulfonation of Benzene
SO3 + H2SO4 -- > SO3H-Benzene, H2SO4 [OH group on sulfur]
Reverse Sulfonation
SO3H-Benzene + H2O + H2SO4 + 100* --> H-Benzene + H2SO4
Friedel-Crafts Alkylation of Benzene
Benzene + RX/AlX3 --> R-Benzene + HX
Friedel-Crafts Acylation of Benzene
Benzene + R(C=O)X/AlX3 --> Benzene-(C=O)R + HX
NH2, NHR, NR2
Strong Activators
-(N-H)-(C=O)-R
Strong Activator
OH
Strong Activator
OR
Strong Activator
CH3, C6H5
Weak Activator
F, Cl, Br, I
Weak Deactivators
NO2
Meta Director
SO3H
Meta Director
CN
Meta Director
CF3
Meta Director
Converting between NO2 and NH2
Zn(Hg), HCL
Clemmensen Reduction
Aldehyde or ketone heated with Zn(Hg) in HCL to strip off oxygen
Reverse Sulfonation [Protection Group]
H+, H2O, Heat
Imine Formation
Carbonyl + NH2-R --> =(N:)-R
Enamine
Carbonyl + R - NH - R --> -(N-R)-R
Wolf-Kischner Reduction (of Carbonyls)
Carbonyl + NH2-NH2/KOH --> Propane
NBS
Raney Nickel and H2
Adds hydrogen to Carbonyl Carbon and Carbonyl Oxygen making it OH
R-MgBr
Makes Carbonyl Oxygen an OH and adds a R to the carbonyl Carbon