Chapter 8: ARENES

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To be classified as aromatic, a compound must meet both of the following criteria: It must have an un-interrupted cyclic p cloud above & below the plane of the molecule. The p cloud must contain (4n + 2) p electrons (n = 0, 1, 2…).

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Nội dung Text: Chapter 8: ARENES

ORGANIC CHEMISTRY Dr Nam T. S. Phan Faculty of Chemical Engineering HCMC University of Technology Office: room 211, B2 Building Phone: 8647256 ext. 5681 Email: ptsnam@hcmut.edu.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 6π e=4x1+2 3
Aromatic: (+) (-) (+) N O S H 4
NOT aromatic: NOT (4n + 2) π e (.) (-) (+) (.) 4π e 5π e 7π e 8π e Interrupted cyclic π cloud 5
NOMENCLATURE OF MONOSUBSTITUTED BENZENES Name of substituent + benzene 6
Names have to be memorized: 7
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
Alphabetical Lowest possible order numbers 10
PREPARATION OF BENZENE Petroleum Bezene 11
REACTIONS OF BENZENE Halogenations of benzene 12
Reaction mechanism: electrophilic substitution Catalyst regeneration 13
Nitration of benzene 14
Sulfonation of benzene Reversible reaction 15
Reaction mechanism: electrophilic substitution 16
Friedel-Crafts Alkylations of benzene 17
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Carbocation rearrangement 19
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