厦门大学化学化工学院：《有机化学》课程教学资源（课件讲稿，双语版）第十四章 芳香化合物（14.3-14.7）Reactions of Benzene

ORGANIC CHEMISTRY Chapter 14 143 Reactions of benzene Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 14 14.3 Reactions of Benzene

ORGANIC CHEMISTRY Chapter 14 Br/CCI 14 dark.25°C No addition of bromine KMnO/ho No oxidation 25°C HT/HO No hydration heat H/Ni Slow addition at high temperature and pressure Br BI +HBi Febr3 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 14 Br2/CCl4 dark, 25°C KMnO4/H2O 25°C H+/H2O heat H2/Ni No addition of bromine No oxidation No hydroation Slow addition at high temperature and pressure Br + HBr Br2 FeBr3

ORGANIC CHEMISTRY Chapter 14 14 4 The Kekule structure for benzene Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 14 14.4 The Kekulé Structure for Benzene

ORGANIC CHEMISTRY Chapter 14 1865~1899 Kekule, 1865 Dewar, 1866-1867 Ladenburg, 1869 Armstrong-Baeyer Claus, 1888 Thiele, 1899 1887~1888 Br Br Br Br Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 14 1865 1899 Kekulé, 1865















Dewar, 1866~1867 Ladenburg, 1869




























































































Armstrong-Baeyer 1887~1888 Thiele , 1899 Br Br Br Br Claus , 1888

ORGANIC CHEMISTRY Chapter 14 14 4.5 The Stability of benzene Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 14 14.5 The Stability of Benzene

ORGANIC CHEMISTRY Chapter 14 △H°(kJ/mo1) Pt 120 +2H2 32 +3H 208 120×3=360(kJ/mo) 360-208=152 (kJ/mol)-Resonance energy Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 14 ∆H°( kJ/mol) + H2 Pt + 2H2 Pt + 3H2 Pt 120 232 208 120 3 = 360 (kJ/mol) 360 208 = 152 (kJ/mol) —— Resonance energy

ORGANIC CHEMISTRY Chapter 14 14.6 Modern Theories of the structure of benzene Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 14 14.6 Modern Theories of the Structure of Benzene

ORGANIC CHEMISTRY Chapter 14 14.6A The Resonance Explanation of the structure of benzene Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 14 14.6A The Resonance Explanation of the Structure of Benzene I II III

ORGANIC CHEMISTRY Chapter 14 14.6b The molecular orbital Explanation of the Structure of benzene H h= H H Antibonding 井2#号 Bonding Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 14 14.6B The Molecular Orbital Explanation of the Structure of Benzene Ψ1 Ψ2 Ψ3 Ψ4 Ψ5 Ψ6 Antibonding Bonding

ORGANIC CHEMISTRY Chapter 14 14.7 Huckel's Rule: The(4n+ 2)T Electron rule Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 14 14.7 Hückel’s Rule: The (4n + 2)π Electron Rule