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Chapter 11 - Arenes and Aromaticity. 11.1 Increasing Unsaturation in 6-Membered Rings. YSU. 11.2 Evidence of structure: all C-C bonds are the same length, all H’s are equivalent. Kekule (1866) - rapidly interconverting isomers?.
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Chapter 11 - Arenes and Aromaticity 11.1 Increasing Unsaturation in 6-Membered Rings YSU
11.2 Evidence of structure: all C-C bonds are the same length, all H’s are equivalent. Kekule (1866) - rapidly interconverting isomers? Robinson (1920) - the two Kekule forms are resonance contributors YSU
11.2-11.3 Bond distances and bond angles of benzene Figure 11.1 Robinson - “AromaticSextet” depiction YSU
11.4 The Stability of Benzene Figure 11.2 YSU
11.5 Orbital Hybridization View of Bonding in Benzene Figure 11.3 i.e. each carbon experiences the same electron density, the six pi electrons are delocalized over the entire molecule YSU
11.6 The molecular orbitals of benzene Figure 11.4 YSU
11.7 Nomenclature of Substituted Benzenes Many common names, however IUPAC systematic names often easier to work out YSU
11.7 Nomenclature of Disubstituted Benzenes Can use numbering or o, m, p nomenclature systems YSU
Not Covering 11.8 11.9 11.11 YSU
11.12 Free-Radical Halogenation of Alkylbenzenes Figure 11.9 YSU
11.14-11.15 Nucleophilic Substitution on Benzylic Halides • SN2 applies with good nucleophiles on 1o and 2o carbons • SN1 applies with weak nucleophiles – good carbocation • E2 competes with more basic nucleophiles on 2o and 3o YSU
11.16 Preparation of Alkenylbenzenes 11.17 Addition to Alkenylbenzenes YSU
Not Covering 11.18 11.19 YSU
11.20 Hückel’s Rule Fig. 11.12 Aromatic = 4n+2 p electrons and flat p system YSU
Not Covering 11.21 YSU
11.22 Aromatic Ions Fig. 11.13 Fig. 11.14 Cation easy to form pKa ~ 16 YSU
11.24 Heterocyclic Aromatic Compounds– Hückel’s Rule Fig. 11.15 YSU
