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