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Dr. Glaser's Visualization Center
To accompany Bruice, Organic Chemistry, 3/e, Chapter 15

Theme Molecule Name Chemical Formula
Isomerism of Benzenes fluorobenzene (S), Properties C6H5F
Isomerism of Benzenes ortho-difluorobenzene (S), Properties C6H4F2
Isomerism of Benzenes meta-difluorobenzene (S), Properties C6H4F2
Isomerism of Benzenes para-difluorobenzene (S), Properties C6H4F2
Isomerism of Benzenes 1,2,3-trifluorobenzene (S), Properties C6H3F3
Isomerism of Benzenes 1,2,4-trifluorobenzene (S), Properties C6H3F3
Isomerism of Benzenes 1,3,5-trifluorobenzene (S), Properties C6H3F3
Benzyne Mechanism ortho-benzyne (S) C6H4
Polycyclic Aromatic Hydrocarbons naphthalene (S) C10H8
Polycyclic Aromatic Hydrocarbons 1-chloronaphthalene (S) C10H7Cl
Polycyclic Aromatic Hydrocarbons 2-chloronaphthalene (S) C10H7Cl
Polycyclic Aromatic Hydrocarbons anthracene (S) C14H10
Polycyclic Aromatic Hydrocarbons phenanthrene (S) C14H10
Polycyclic Aromatic Hydrocarbons pyrene (S), Properties C16H10
Polycyclic Aromatic Hydrocarbons benzo[a]pyrene (S), Properties C20H12
Polycyclic Aromatic Hydrocarbons benzo[e]pyrene (S), Properties C20H12

[a] The structure of the benzyne was optimized at MP2(full)/6-31G*.
[b] Unless otherwise noted, structures were optimized at the ab initio level RHF/6-31G*.