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Bài giảng Organic chemistry - Chapter 8: Arenes - Phan Nam

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ORGANIC CHEMISTRY  
Dr Nam T. S. Phan  
Faculty of Chemical Engineering  
HCMC University of Technology  
Office: room 211, B2 Building  
Phone: 38647256 ext. 5681  
Email: [email protected].vn  
1
Chapter 8: ARENES  
Benzene  
2
CRITERIA FOR AROMATICITY  
To be classified as aromatic, a compound must  
meet both of the following criteria:  
• It must have an un-interrupted cyclic π cloud  
above & below the plane of the molecule  
• The π cloud must contain (4n + 2) π electrons (n  
= 0, 1, 2…)  
un-interrupted  
cyclic π cloud  
6 π e = 4 x 1 + 2  
3
Aromatic:  
(+)  
(-)  
(+)  
N
O
S
H
4
NOT aromatic:  
NOT (4n + 2) π e  
(.)  
(-)  
(+)  
(.)  
7 π e  
4 π e  
5 π e  
8 π e  
Interrupted  
cyclic π  
cloud  
5
NOMENCLATURE OF  
MONOSUBSTITUTED BENZENES  
Name of substituent + benzene  
Names have to be memorized:  
NOMENCLATURE OF DI- &  
POLYSUBSTITUTED BENZENES  
Alphabetical order, 1-position for the 1st stated substituent  
8
1 of the substituents can be incorporated into a name:  
Names  
incorporating  
2 substituents  
9
Lowest possible  
numbers  
Alphabetical  
order  
PREPARATION OF BENZENE  
Petroleum  
Bezene  
11  
REACTIONS OF BENZENE  
Halogenations of benzene  
12  
Reaction mechanism: electrophilic substitution  
13  
Catalyst regeneration  
Nitration of benzene  
14  
Sulfonation of benzene  
Reversible reaction  
15  
Reaction mechanism: electrophilic substitution  
16  
Friedel-Crafts Alkylations of benzene  
17  
18  
Carbocation  
rearrangement  
20  
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