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Br2/FeBr3 or Cl2/FeCl3
halogenation of benzene

HNO3/H2SO4
nitration of benzene (NO2)

SO3/H2SO4
Sulfonation of Benzene

RCl/AlCl3
Friedel-Crafts Alkylation

ClCOR/AlCl3
Friedel-Crafts Acylation

product of nitration of benzene
NO2
Product of sulfonation of benzene
SO3H
Limitations of Alkylation
1. Cannot alkylate rings with EWG
2. Rxn is hard to control, so will receive multiple alkylations on same molecule
3. Carbocation Rearrangement: may not get desired product
Limitations of acetylation
Can't react with EWG
CO, HCl/AlCl3, CuCl
add aldehyde to a ring

Zn(Hg), HCl
reduces carbonyl to alkane

1. Zn/HCl 2.NaOH
Reduces Nitro group to Amino


Is Ester an EWG or EDG?
EDG

Is alkoxide an EWG or EDG?
Strongly EDG

Is hydroxy an EWG or EDG?
EDG

is Amide an EWG or EDG?
EDG

is Amine an EWG or EDG?
Strongly EDG

is Methyl an EWG or EDG?
Weakly EDG

Is ethyl an EWG or EDG?
Weakly EDG

Is isopropyl an EWG or EDG
Weakly EDG

Is Carbonyl an EWG or EDG?
EWG

Is Sulfonyl an EWG or EDG?
EWG

Is cyano an EWG or EDG?
Strongly EWG

Is Nitro an EWG or EDG?
Strongly EWG

Is haloalkyl an EWG or EDG?
Strongly EWG

Is Ammonium an EWG or EDG?
Strongly EWG