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48 Cards in this Set
- Front
- Back
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X= CL
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chlorobenzene
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X= NO2
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nitrobenzene
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X= CH3
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toluene
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X= NH2
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aniline
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X= OH
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phenol
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X= CO2H
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benzoic acid
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X= SO3H
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benzenesulfonic acid
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X= OCH3
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anisole
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X= CHO
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benzaldehyde
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X= CN
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benzonitrile
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X= NHCOCH3
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acetanilide
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X= COCH3
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acetophenone
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X= CO2CH3
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methyl benzoate
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types of E+
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SO3, +SO3H, FeBR3-, Cl3Fe- Cl+,
"I+", H-O-O+ H2, C+, +C=O, +NO2 |
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Ortho/Para -Directors
Activating Strong |
Influence: EDG by Resonance
NH2, NHR, NR2, OH, O- w/non-bonding electrons |
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Ortho/Para -Directors
Activating Medium |
Influence: EDG by Resonance
OR, NHCOCH3 w/ non-bonding electron pairs |
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Ortho/Para -Directors
Activating Weak |
Influence: EDG by induction only
R (alkyl), C6H6- (phenyl) |
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Ortho/Para -Directors
Deactivating Weak |
Influence: Induction controls reactivity (EWG) but resonance controls orientation taken by electrophile
F, Cl, Br, I (halogens) |
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Meta-Directors
Deactivating Strong |
Influence: EWG by induction and resonance
NO2, CN |
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Meta-Directors
Deactivating Medium |
Influence: EWG by induction and resonance
CO2H, CO2R, CHO, COR, CONHR, SO3H |
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Meta-Directors
Deactivating Weak |
Influence: EWG by induction
NH3+, NH2R+, NHR2+ |
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EDG by Resonance
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G= non-bonding electron-pair
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EDG by induction
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G= an alkyl group
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EWG by induction
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G= electronegative group
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EWG by induction and resonance
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G= electronegative group
G=Y (G double-bonded to substituent group) |
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SO3
H2SO4 |
+SO3H
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Br2
FeBr3 |
+Br
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HNO3
H2SO4 |
+NO2
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Cl2
AlCl3 |
+Cl
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I2
CuCl2 |
+I
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HSO3F
H2O2 |
+OH
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1)KOH
2)R-X |
+O-R
(this happens w/ either an OH group on the ring or when HSO3F H2O2 have reacted with benzene) |
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H2
Pd/C |
takes away C=O groups & replaces w/ H+
+NH2 -C=O (acylation) |
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Acylation
RCOCl AlCl3 |
+R-C=O (ketone)
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KMnO4
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+CO2H
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Alkylation
RCl AlCl3 |
+R-group
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Diazonium salts
HNO2 NaNO2 HCl |
-H2
+N2 |
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Diazonium salts
CuCl |
+Cl
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Diazonium salts
CuBr |
+Br
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Diazonium salts
CuCN |
+CN
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Diazonium salts
D3PO2 |
+D
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Diazonium salts
KI |
+I
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Diazonium salts
H2O, H+ |
+OH
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Diazonium salts
H3PO2 |
+H
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Diazonium salts
HBF4 heat |
+F
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NaNH2
NH3 |
Benzyne
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heat
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Benzyne
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NBS
light heat |
+Br
takes an H+ |
