Benzene and Aromaticity - PowerPoint PPT Presentation

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Benzene and Aromaticity

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Benzene and Aromaticity Bonding in Benzene Proposed Benzene Structures C6H6 reacts with HBr to form one isomer of C6H5Br Other Conjugated Hydrocarbon Rings Annulenes ... – PowerPoint PPT presentation

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Title: Benzene and Aromaticity


1
Benzene and Aromaticity
2
Bonding in Benzene
3
Proposed Benzene Structures
4
C6H6 reacts with HBr to form one isomer of C6H5Br
5
Other Conjugated Hydrocarbon RingsAnnulenes
6
DHhyd Data Illustrates Stability
7
Benzene Representations
8
Molecular Orbitals of Benzene
9
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10
M.O.s of Cyclobutadiene
11
6 p Electrons is Stable4 or 8 p Electrons is not
12
Huckels Rule 4N 2
13
In Order to Exhibit Aromaticity a Compound Must
  • -         Cyclic
  • -         Planar
  • -         Conjugated throughout
  • -         Has a Huckel of p electrons
  • o       4N 2 where N is any integer or 0
  •          hence, 2,6,10,14 p e-

14
Naphthalene
15
Pyridine, an Aromatic Heterocycle
16
Pyridine as a Base
17
Pyrrole
18
Pyrrole as a Base
19
Other Aromatic Heterocycles
20
Cyclopentadiene as an AcidpKa 16
21
Cyclopentadienyl ionOne is Aromatic, one is
Antiaromatic
22
Resonance Depictions of the Ions
23
Tropylium Ion
24
Aromatic?
25
Aromatic, Anti-Aromatic or Nonaromatic?
26
Some Well-known Aromatic Compounds
27
Designer Drugs
28
Nomenclature
29
Disubstitutionortho, meta and para
30
Disubstitution Nomenclature
31
Aromatic Template Names
32
More Common Names
33
Aromatic Ring as a Substituent
34
Name These
35
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