教学课件学术资源col大学有机化学课件html.pptxVIP

11.18Cyclobutadiene and Cyclooctatetraene;cyclic conjugation is necessary, but not sufficient ;heat of hydrogenation of benzene is 152 kJ/mol less than 3 times heat of hydrogenation of cyclohexene;Heats of Hydrogenation;structure of a stabilized derivative is characterizedby alternating short bonds and long bonds;Structure of Cyclooctatetraene;Conclusion;11.19Hückels Rule:Annulenes;among planar, monocyclic, completely conjugated polyenes, only those with 4n + 2 p electrons possess special stability (are aromatic) n 4n+2 0 2 1 6 2 10 3 14 4 18;among planar, monocyclic, completely conjugated polyenes, only those with 4n + 2 p electrons possess special stability (are aromatic) n 4n+2 0 2 1 6 benzene! 2 10 3 14 4 18;Hückel restricted his analysis to planar,completely conjugated, monocyclic polyenes he found that the p molecular orbitals ofthese compounds had a distinctive pattern one p orbital was lowest in energy, another was highest in energy, and the others were arranged in pairs between the highestand the lowest;;;;;;;p-Electron Requirement for Aromaticity;Completely Conjugated Polyenes;Annulenes are planar, monocyclic, completely conjugated polyenes. That is, they are the kind of hydrocarbons treated by Hückels rule.;predicted to be aromatic by Hückels rule,but too much angle strain when planar and all double bonds are cis 10-sided regular polygon has angles of 144°;incorporating two trans double bonds intothe ring relieves angle strain but introducesvan der Waals strain into the structure andcauses the ring to be distorted from planarity;incorporating two trans double bonds intothe ring relieves angle strain but introducesvan der Waals strain into the structure andcauses the ring to be distorted from planarity;14 p electrons satisfies Hückels rule van der Waals strain between hydrogens insidethe ring;16 p electrons does not satisfy Hückels rule alternating short (134 pm) and long (146 pm) bonds not aromatic;18 p ele