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z-Ch. 16 RXN
CHM2211 Dr. Elsheimer Fall 09
13
Organic Chemistry
Undergraduate 2
09/06/2009

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Term
Bromination
Definition
Br2/FeBr3 Benzene -> Benzene-Br
Term
Chlorination
Definition
Cl2/FeCl3 Benzene -> Benzene-Cl
Term
Iodination
Definition
I2/CuCl2 Benzene -> Benzene-I
Term
Nitration
Definition
HNO3/H2SO4 Benzene -> Benzene-NO2
Term
Sulfonation
Definition
SO3/H2SO4 Benzene -> Benzene-SO3H
Term
Friedel-Crafts
Definition
CH3Cl/AlCl3 Benzene -> Benzene-CH3
CHC(=O)Cl/AlCl3 Benzene -> Benzene-C(=O)CH3

1.R-X must be alkyl halide. Vinyl or aryl won’t work
2.Does not work on strongly deactivated rings
3.No reaction if NH2, NHR, or NR2 on ring
4.Alkyl is activating. Second alkylation faster than first.
Reaction only practical with large excess of benzene so that statistics control product ratio.
5.1° R+ rearranges to more stable 2°
Term
Reduction of aromatic nitro groups
Definition
1.Fe,H3O+/2.HO- Benzene-NO2 -> Benzene-NH2
Term
Nucleophilic aromatic substitution by addition to activated aryl halides
Definition
Na+ -OH/H2O

halide to OH
Term
Nucleophilic aromatic substitution by formation of benzyne intermediate from unactivated aryl halide
Definition
Na+ -NH2/NH3 Benzene-Br -> Benzene-NH2
Term
Oxidation of alkylbenzene side chain
Definition
KMnO4/H2O Benzene-CH3 -> Benzene-COOH
Term
Benzylic bromination of alkylbenzene side chain
Definition
NBS/CCl4 Benzene-Ch3 -> Benzene-CH2Br
Term
Catalytic hydrogenation or aromatic rings
Definition
H2/(Rh/C) catalyst Benzene -> cyclohexane
Term
Reduction of aryl alkyl ketones
Definition
(H2/Pd)/ethanol Benzene-C(=O)-R -> Benzene-CH2-R
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