history of benzene
DESCRIPTION
1824 - 1825 Isolated from burnt whale oil by Michael Faraday 1834 Eilhardt Mitscherlich finds benzene has formula of C 6 H 6 1861 Loschmidt proposes structure for benzoic acid and aniline. History of Benzene. 1824 - 1825 Isolated from burnt whale oil by Michael Faraday - PowerPoint PPT PresentationTRANSCRIPT
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History of Benzene1824 - 1825 Isolated from burnt whale oil by Michael Faraday1834 Eilhardt Mitscherlich finds benzene has formula of C6H6
1861 Loschmidt proposes structure for benzoic acid and aniline
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History of Benzene1824 - 1825 Isolated from burnt whale oil by Michael Faraday1834 Eilhardt Mitscherlich finds benzene has formula of C6H6
1861 Loschmidt proposes structure for benzoic acid and aniline
O
OH
N
H
H
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History of Benzene1865 Kekule has a dream1865 Kekule invokes sausage diagramsBulletin de la Société Chimique de France, 3, 98 (1865)
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10–4
History of Benzene1865 Kekule has a dream1865 Kekule invokes sausage diagramsBulletin de la Société Chimique de France, 3, 98 (1865)
1866 Kekule introduces ring model for benzene
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Alternate Benzene Structures
Dewar 18671972
proposedsynthesized
Landenburg Prismane
18691973
Claus18671967
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Fig. 15-2, p. 521
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Hückel’s Rules for aromaticity
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p. 521
H
H
H
H
H
H
Benzene electron distribution map
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Fig. 15-12, p. 532
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Hückel’s Rules for aromaticity
Aromaticity vs. antiaromaticity
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p. 523
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p. 524
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Hückel’s Rules for aromaticity
Aromaticity vs. antiaromaticity
Why 4n + 2 for aromatic and 4n for antiaromatic?Frost’s cycle
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Fig. 15-3, p. 522
Benzene Molecular Orbitals
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Cyclopentadienyl ions
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Fig. 15-11, p. 531
H H H
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Fig. 15-5, p. 526
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Fig. 15-7, p. 527
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Fig. 15-9a, p. 529
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Fig. 15-9b, p. 529
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17%
27%
57% A. Aromatic
B. Antiaromatic
C. Neither
5. 14-annulene
NN
OCH3CH3O
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Pyridyl DHA Targets
NN
OCH3CH3O
N
N
OCH3CH3O
NN
OCH3CH3O1+2 1+2 1+0, 1+2 none 1+0 1+0
N
N
CH3O OCH3
N
N
CH3O OCH3
N
N
CH3O OCH3
N
N
CH3O OCH3
2+1 1+1 2+0, 2+1 none none 1+0, 1+1 2+0 1+0
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Fig. 15-14, p. 535
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p. 535
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p. 540
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p. 535
TIPSTIPS
Br Br
19 11
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Aromatic Biomolecules
1.Amino acids2.Nucleic acids
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Fig. 15-8, p. 528
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Fig. 15-9, p. 529
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p. 533
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p. 529
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p. 533
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p. 530
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p. 540
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p. 541
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p. 337
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p. 338
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Table 9-2, p. 337
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Summary
-H (unsubstituted)
-R or -Ar, ortho- and para- -R or -Ar, meta-
-NH2 or -OH, meta-
-NH2 or -OH, ortho- and para-
-Cl or -Br, ortho- and para-
-Cl or -Br, meta-
-NO2 or -CO2H, meta-
-NO2 or -CO2H, ortho- and para-
Deactivators
Activators
Reactants
[CarbocationIntermediate]
Reaction Progress
Energy
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Fig. 9-16, p. 338
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p. 340
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p. 345