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COMPOUNDS
Aromatic
STRUCTURE OF BENZENE
Or simply
Or
NOMENCLATURE OF
AROMATIC COMPOUNDS
1.
Monosubstituted benzenes
A substituted benzene is by replacing one
Chlorobenzene
ethylbenzene
NO2
nitrobenzene
Toluene
phenol
benzoic acid
benzaldehyde
anline
CH3
- CH 2|
- CHCHClCH2CH3
diphenylmethane
3-chloro-2-phenylpentane
2.
Disubstituted benzenes
When two substituted groups replace two
hydrogen atoms in a benzene molecule, three
different isomeric compounds are possible. The
prefix ortho-(o), meta-(m-), and para-(p-) are
used to name disubstituted benzens in one
nomenclature system. Ortho designates 1,2
disubstitution, meta reprsents 1,3 disubtitution,
and para designates 1,4 disubtitution.
Consider the dichlorobenzens, C 6H4Cl2
Cl
Cl
Cl
|
|
Cl
|
Cl
o-dichlorobenzene
Cl
m-dichlorobenzene
dichlorobenzene
(1,2-dichlorobenzene) (1,3-dichlorobenzene)
dicholorobenzene)
p( 1,4-
xylene
CH3
|
CH3
CH3
CH3
CH3
CH3
O-xylene
m-xylene
p-xylene
When the two susbstituents are different and
neither is part of a compound with a special
name. The names of the two substituent are
given in alphabetical order, followed by the
word benzene.
NO2
Cl
3. Polysubstituted benzenes
When there are more than two substituted
Cl
Br
1,2,4-tribromobenzene
5-bromo-2-chlorophenol
Naphtalene
phenanthrene
anthracene
CHEMICAL REACTION OF
BENZENE AND
ALXYLBENZENES
2. Halogenation of benzene
Bromine reacts with benzene in the
3. Nitration of benzene
Warning benzene with a mixture of
4.
C6H6 + CH3CH2Br
H2 O
ArCl3
C6H5SO3H +
C H
+ CH COCl
AlCl
C H COCH
6. Oxidation of alkylbenzenes
An alkyl side chain on a benzene ring is
-CH2CH3 + (O)
- COOH
O2N-
-COOH
7. Halogenation of alkylbenzenes
Side-chain halogenation of toluene can
|
Cl2
uv
|
Cl2
uv
|
Cl2
uv
benzal chloride
Toluene
benzene triflouromethylbenzene
Most reactive
least reactive
EFFECT ON
RATE
Very strongly
activating
Strongly
activating
Activating
SUBSTITUENT
-NH2
Amano
-NHR
Alkylamino
-NH2
dialkylami
no
-OH
hydroxyl
-NHCOR Acylamino
-OR
Alkoxyl
-R
Alkyl
EFFECT ON
ORIENTATION
ortho-para
directing
Ortho-para
directing
Ortho-para
directing
Deactivating
-X
Halogen
Ortho-para
directing
Strongly
deactivating
-CHO
Formyl
Meta directing
-COR
Acyl
-COOH Carboxyl
-COOR Ester
Very strongly
deactivating
-COCl
Acyl
choloride
-CN
Cyano
-SO3H
Sulfuric acid
-CF3
Triflouromet
hyl
-NO2
nitro
Meta directing
MULTIPLE SUBSTITUENT
EFFECTS
When a benzene ring bears two or more
substituents, noth its reactivity and
orientation of further substitution can, in
most cases, be predicted from the
cumulative effects of its substituents.
CH3
CH3
|
O O
| COCH3
+ CH3COCCH3
AlCl
3
CH3
P-xylene
CH3
2,5-dimethylacetophenone
NHCH3
|
NHCH3
|
+ Br2
Br
HAr
Cl
4-chloro-N-methylaniline
methylaniline
Cl
2 bromo-4chloro-N-
|
+ HO NO2
|
C(CH3)3
P-tert-butyltouluene
NO2
H2SO4
|
C(CH3)3
4-tert-butyl-2-nitrotoluene
|
+ HO NO2
CH3
H2SO4
| CH3
NO2
m-xylene
2,4-dimethyl-1-nitrobenzene
AROMATIc
COMPOUNDS
SUBMITTED BY : SHERLENE A.
GESIM
SUBMITTED TO: MRS.
ELIZABETH VIVAR