23
Electrophilic Aromatic Substitution Reaction Pattern Variation o,p vs. m
| Date post: | 03-Jan-2016 |
| Category: |
Documents |
| Upload: | fabrizio-bellew |
| View: | 29 times |
| Download: | 1 times |
Electrophilic Aromatic Substitution
Reaction Pattern Variation
o,p vs. m
Electron Withdrawing Substituents
FeCl3CH
ClH Cl FeCl3
CH3O O CH3
o-substitutionδ
δ
o
ClCl
Electron Withdrawing Substituents
FeCl3CH
ClH Cl FeCl3
CH3O O CH3
o-substitutionδ
δ
o
ClCl H
Cl Cl FeCl3
O CH3
δ
δ
o
Electron Withdrawing Substituents
FeCl3CH
ClH Cl FeCl3
CH3O O CH3
o-substitutionδ
δ
o
ClCl H
Cl Cl FeCl3
O CH3
δ
δ
o
H
C
Cl Cl FeCl3
O CH3 mCCH3O
FeCl3Cl Clδ
δm-substitution
Electron Withdrawing Substituents
FeCl3CH
ClH Cl FeCl3
CH3O O CH3
o-substitutionδ
δ
o
ClCl H
Cl Cl FeCl3
O CH3
δ
δ
o
H
C
Cl Cl FeCl3
O CH3 mCCH3O
FeCl3Cl Clδ
δ
H
C
Cl Cl FeCl3
O CH3 m
δ
δm-substitution
Electron Withdrawing Substituents
FeCl3CH
ClH Cl FeCl3
CH3O O CH3
o-substitutionδ
δ
o
ClCl H
Cl Cl FeCl3
O CH3
δ
δ
o
H
C
Cl Cl FeCl3
O CH3 mCCH3O
FeCl3Cl Clδ
δ
H
C
Cl Cl FeCl3
O CH3 m
δ
δ
C
HCl Cl FeCl3
CH3O
δ
CCH3O
FeCl3Cl Cl
m-substitution
p-substitution
p
δ
Electron Withdrawing Substituents
FeCl3CH
ClH Cl FeCl3
CH3O O CH3
o-substitutionδ
δ
o
ClCl H
Cl Cl FeCl3
O CH3
δ
δ
o
H
C
Cl Cl FeCl3
O CH3 mCCH3O
FeCl3Cl Clδ
δ
H
C
Cl Cl FeCl3
O CH3 m
δ
δ
C
HCl Cl FeCl3
CH3O
δ
CCH3O
FeCl3Cl Cl
m-substitution
p-substitution
p
δ
C
HCl Cl FeCl3
CH3O
δ
p
δ
Electron Withdrawing Substituents
FeCl3CH
ClH Cl FeCl3
CH3O O CH3
o-substitutionδ
δ
o
ClCl H
Cl Cl FeCl3
O CH3
δ
δ
o
H
C
Cl Cl FeCl3
O CH3 mCCH3O
FeCl3Cl Clδ
δ
H
C
Cl Cl FeCl3
O CH3 m
δ
δ
C
HCl Cl FeCl3
CH3O
δ
CCH3O
FeCl3Cl Cl
m-substitution
p-substitution
p
δ
C
HCl Cl FeCl3
CH3O
δ
p
δ
Electron Withdrawing Substituents
FeCl3CH
ClH Cl FeCl3
CH3O O CH3
o-substitutionδ
δ
o
ClCl H
Cl Cl FeCl3
O CH3
δ
δ
o
H
C
Cl Cl FeCl3
O CH3 mCCH3O
FeCl3Cl Clδ
δ
H
C
Cl Cl FeCl3
O CH3 m
δ
δ
C
HCl Cl FeCl3
CH3O
δ
CCH3O
FeCl3Cl Cl
m-substitution
p-substitution
p
δ
C
HCl Cl FeCl3
CH3O
δ
p
δ
Electron Withdrawing Substituents
FeCl3CH
ClH Cl FeCl3
CH3O O CH3
o-substitutionδ
δ
o
ClCl H
Cl Cl FeCl3
O CH3
δ
δ
o
H
C
Cl Cl FeCl3
O CH3 mCCH3O
FeCl3Cl Clδ
δ
H
C
Cl Cl FeCl3
O CH3 m
δ
δ
C
HCl Cl FeCl3
CH3O
δ
CCH3O
FeCl3Cl Cl
m-substitution
p-substitution
p
δ
C
HCl Cl FeCl3
CH3O
δ
p
δ
Electron Withdrawing Substituents
FeCl3CH
ClH Cl FeCl3
CH3O O CH3
o-substitutionδ
δ
o
ClCl H
Cl Cl FeCl3
O CH3
δ
δ
o
H
C
Cl Cl FeCl3
O CH3 mCCH3O
FeCl3Cl Clδ
δ
H
C
Cl Cl FeCl3
O CH3 m
δ
δ
C
HCl Cl FeCl3
CH3O
δ
CCH3O
FeCl3Cl Cl
m-substitution
p-substitution
p
δ
C
HCl Cl FeCl3
CH3O
δ
p
δ
Least Increase
Electron Donating SubstituentsFeCl3NH2 H
ClH Cl FeCl3o-substitutionδ
δ
o
ClCl
NH2
Electron Donating Substituents
FeCl3NH2 HClH Cl FeCl3o-substitution
δ
δ
o
ClCl H
Cl Cl FeCl3δ
δ oNH2 NH2
Electron Donating Substituents
FeCl3NH2 HClH Cl FeCl3o-substitution
δ
δ
o
ClCl H
Cl Cl FeCl3δ
δ o
H
Cl Cl FeCl3
m
FeCl3Cl Clδ
δm-substitution
NH2 NH2
NH2 NH2
Electron Donating Substituents
FeCl3NH2 HClH Cl FeCl3o-substitution
δ
δ
o
ClCl H
Cl Cl FeCl3δ
δ o
H
Cl Cl FeCl3
m
FeCl3Cl Clδ
δ
H
Cl Cl FeCl3
m
δ
δm-substitution
NH2 NH2
NH2 NH2 NH2
Electron Donating Substituents
FeCl3NH2 HClH Cl FeCl3o-substitution
δ
δ
o
ClCl H
Cl Cl FeCl3δ
δ o
H
Cl Cl FeCl3
m
FeCl3Cl Clδ
δ
H
Cl Cl FeCl3
m
δ
δ
HCl Cl FeCl3
δFeCl3Cl Cl
m-substitution
p-substitution
p
δ
NH2 NH2
NH2 NH2 NH2
NH2NH2
Electron Donating Substituents
FeCl3NH2 HClH Cl FeCl3o-substitution
δ
δ
o
ClCl H
Cl Cl FeCl3δ
δ o
H
Cl Cl FeCl3
m
FeCl3Cl Clδ
δ
H
Cl Cl FeCl3
m
δ
δ
HCl Cl FeCl3
δFeCl3Cl Cl
m-substitution
p-substitution
p
δH
Cl Cl FeCl3δ
pδ
NH2 NH2
NH2 NH2 NH2
NH2NH2 NH2
Electron Donating Substituents
FeCl3NH2 HClH Cl FeCl3o-substitution
δ
δ
o
ClCl H
Cl Cl FeCl3δ
δ o
H
Cl Cl FeCl3
m
FeCl3Cl Clδ
δ
H
Cl Cl FeCl3
m
δ
δ
HCl Cl FeCl3
δFeCl3Cl Cl
m-substitution
p-substitution
p
δH
Cl Cl FeCl3δ
pδ
NH2 NH2
NH2 NH2 NH2
NH2NH2 NH2
Electron Donating Substituents
FeCl3NH2 HClH Cl FeCl3o-substitution
δ
δ
o
ClCl H
Cl Cl FeCl3δ
δ o
H
Cl Cl FeCl3
m
FeCl3Cl Clδ
δ
H
Cl Cl FeCl3
m
δ
δ
HCl Cl FeCl3
δFeCl3Cl Cl
m-substitution
p-substitution
p
δH
Cl Cl FeCl3δ
pδ
NH2 NH2
NH2 NH2 NH2
NH2NH2 NH2
Electron Donating Substituents
FeCl3NH2 HClH Cl FeCl3o-substitution
δ
δ
o
ClCl H
Cl Cl FeCl3δ
δ o
H
Cl Cl FeCl3
m
FeCl3Cl Clδ
δ
H
Cl Cl FeCl3
m
δ
δ
HCl Cl FeCl3
δFeCl3Cl Cl
m-substitution
p-substitution
p
δH
Cl Cl FeCl3δ
pδ
NH2 NH2
NH2 NH2 NH2
NH2NH2 NH2
Electron Donating Substituents
FeCl3NH2 HClH Cl FeCl3o-substitution
δ
δ
o
ClCl H
Cl Cl FeCl3δ
δ o
H
Cl Cl FeCl3
m
FeCl3Cl Clδ
δ
H
Cl Cl FeCl3
m
δ
δ
HCl Cl FeCl3
δFeCl3Cl Cl
m-substitution
p-substitution
p
δH
Cl Cl FeCl3δ
pδ
NH2 NH2
NH2 NH2 NH2
NH2NH2 NH2
biggest decrease
Experiment 5
O
NH2
NH2
NH2
CH3
Nucleophiles
F
N O
O
N
O
O
Cl
N O
O
N
O
O
Br
N O
O
N
O
O
Aryl Halides
Experiment 5
Nucleophile Aromatic Halide Percent Yield Percent Yield averageP-anisidine 1-fluoro-2,4-dinitrobenzene 108 126 116.88P-anisidine 1-chloro-2,4-dinitrobenzene 96 114 104.75P-anisidine 1-bromo-2,4-dinitrobenzene 38 97 67.615
cyclohexylamine 1-fluoro-2,4-dinitrobenzene 104 98.6 101.5cyclohexylamine 1-chloro-2,4-dinitrobenzene 93 80.4 86.55cyclohexylamine 1-bromo 2,4 dinitrobenzene 72 40 56.1
aniline 1-flouro-2,4-dinitrobenzene 99 97 98.05Aniline 1-chloro-2,4-dinitrobenzene 74 74 aniline 1-bromo-2,4-dinitrobenzene 98 62.5 80.25
cyclohexylamine 1-fluoro-2,4-dinitrobenzene 104 98.6 101.5P-anisidine 1-fluoro-2,4-dinitrobenzene 108 126 117aniline 1-flouro-2,4-dinitrobenzene 99 97 98.05
cyclohexylamine 1-chloro-2,4-dinitrobenzene 93 80.4 86.55P-anisidine 1-chloro-2,4-dinitrobenzene 96 114 104.75Aniline 1-chloro-2,4-dinitrobenzene 74 74
cyclohexylamine 1-bromo 2,4 dinitrobenzene 72 40 56.1P-anisidine 1-bromo-2,4-dinitrobenzene 38 97 67.615aniline 1-bromo-2,4-dinitrobenzene 96.5 71.2 83.85
![NANO EXPRESS Open Access Propargylic substitution ... · Background Electrophilic attack on aromatic carbons is a useful ... [1-3]. Electrophilic aromatic substitution is an organic](https://static.documents.pub/doc/80x56/5b461b0a7f8b9a114c8b5ee0/nano-express-open-access-propargylic-substitution-background-electrophilic.jpg)
