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Benzene

The document discusses the mechanisms, reagents, catalysts, and products of various reactions that can occur with benzene, including halogenation, nitration, sulfonation, Friedel-Crafts alkylation and acylation, hydrogenation, bromination, oxidation, and reduction. It also notes that the reactivity and orientation of substitutions on benzene can be affected by substituent effects. The mechanisms allow benzene to be functionalized through addition of halides, nitro groups, sulfonic acids, alkyl groups, acyl groups, and hydrogen.

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75 views

Benzene

The document discusses the mechanisms, reagents, catalysts, and products of various reactions that can occur with benzene, including halogenation, nitration, sulfonation, Friedel-Crafts alkylation and acylation, hydrogenation, bromination, oxidation, and reduction. It also notes that the reactivity and orientation of substitutions on benzene can be affected by substituent effects. The mechanisms allow benzene to be functionalized through addition of halides, nitro groups, sulfonic acids, alkyl groups, acyl groups, and hydrogen.

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GAMEPORIUM
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Benzene

Mechanism Name Reagent Catalyst Product


a. Br2 a. FeBr3
b. Cl2 b. FeCl3
Halogenation Monohalogenated
c. I2 c. H2O2, CuCl2
d. CuFe2 d. Heat (~500 C)
a. +NO2
a. Nitro substituted
b. In the presence Acid catalyst
Nitration ring (ArNO2)
of Fe/SnCl2 (H2SO4)
b. Arylamine (ArNH2)
(reduction)

Sulfonation Fuming sulfuric acid (SO3 and H2SO4) ArSO3H

SE Friedel-Crafts Alkylation
Substitution with +R
Do not succeed if there’s
RX AlX3
initial substitution of highly
Hydride shift/Alkyl shift
electron-withdrawing
(electrophile -R) (aluminum halide) may occur to form
groups or basic amino
more stable product
group for protonation
(NO2, CN, SO3H AND COR)

RCOX AlX3
Friedel-Crafts Acylation Substitution with +COR
(RCO-Cl, RCO-Br) (AlCl3 , AlBr3)

Pt or Rh metal
AE Hydrogenation H2 catalyst under
high presure
Saturated product

Br2
NBS and benzoyl
Addition of Br to alkyl
SR Bromination
To an alkyl side
peroxide
(Ph(CO2)2)
side chain
chain
Convert the side chain
Oxidation of Alkyl Side
to -COOH (carboxylic
Chain
Acidic Catalyst acid)
Oxi Only oxidize if there is
KMnO4
(H2O, H+)
Regardless of the alkyl
benzylic hydrogen
present
Mechanism Name Reagent Catalyst Product
Aryl alkyl ketone
(product of FC
Acylation)
Red Reduction
Nitro substituted
Pd (H2/Pd) -O becomes -H

(product of
nitration)

Substituent Effects

Reactivity

Orientation

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