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Reactions of Benzene(2)

Reactions of Benzene(2)

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Published by Emmanuel Mantey

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Categories:Types, Reviews
Published by: Emmanuel Mantey on Jan 09, 2013
Copyright:Attribution Non-commercial

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05/14/2014

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1
Chemical properties (reactions)of benzene
Electrophilic Aromatic Substitution (EAS)
EAS 
is a general method of synthesing subsitutedbenzene.•Benzene is sufficientlynucleophilicthat it undergoessubstitution byacyliumions or alkylcarbocationsto givesubstituted derivatives.General reaction:
 
2
General mechanism-two steps:
Step 1:a stabilized carbocationthe cyclohexadienyl cation(arenium ion)
+ E B
H E H EH E
+ B
 
Step 2
:
H E
+ B
E
+ H-B
•Usually the first step is slow and rate-determining.•There is evidence that a weaker
complex forms prior to
complex.
sp
3
carbon
 
3
1.Halogenation of Benzene
HNO
3
(consumed)I
2
 AlCl
3
(catalyst)Cl
2
FeBr 
3
(catalyst)Br 
2
Lewis AcidsX
2
Electrophile Reactant:X
2
/Lewis Acid
+ X
2
X
FeX
3
when X = ClAlCl
3
is also used
X = Cl, Br 

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