Lab #6: Regioselective Nitration of Acetanilide Legend

Solvent: 5:5 Ethyl Acetate and Hexanes S: Sample Spot

C: Co-spot

TLC Plate: Reaction Completion TLC Plate: 2, 4 Dinitro Isomer Reference R: Reference Spot
Reference: Acetanilide
Displacement of
Solvent Front
Rf = 0.93 Rf = 0.93
Rf = 0.93

Rf = 0.81 Rf = 0.81

Rf = 0.71 Rf = 0.71
Rf = 0.60
Rf = 0.60 Rf = 0.60 TLC Plate: Ortho Isomer Reference TLC Plate: Crude Product Reference
4.8 cm 5.8 cm

Rf = 0.40 Rf = 0.40

Rf = 0.23
Rf = 0.23 Rf = 0.21 Rf = 0.21
Rf = 0.75 Rf = 0.75

Rf = 0.60
Rf = 0.58 Rf = 0.58 Rf = 0.58 Rf = 0.58
Rf = 0.58
5.5 cm 5.5 cm
S C R S C R Rf = 0.47
Rf = 0.47
Rf = 0.47
Rf = 0.42
Rf = 0.42

Rf = 0.29 Rf = 0.29
Rf = 0.29
Rf = 0.27 Rf = 0.27
Rf = 0.20 Rf = 0.20 Rf = 0.20

S C R S C R

TLC Plate: Para Isomer Reference TLC Plate: Meta Isomer Reference

TLC Plate: Mother Liquor Reference

Rf = 0.73 Rf = 0.73
Rf = 0.73

Rf = 0.62
Rf = 0.62
Rf = 0.54
Rf = 0.54
5.2 cm 4.8 cm

Rf = 0.38 Rf = 0.41 Rf = 0.41

Rf = 0.38 Rf = 0.38

Rf = 0.54 Rf = 0.54
Rf = 0.27 Rf = 0.27 5.4 cm
Rf = 0.23 Rf = 0.23 Rf = 0.19
Rf = 0.19 Rf = 0.19 Rf = 0.44 Rf = 0.44

Rf = 0.31 Rf = 0.31

Rf = 0.19
Rf = 0.19 Rf = 0.19
S C R S C R

S C R