Benzene animations

http://www.dnatube.com/video/1418/Vagu e-Idea-of-Benzene-Resonance
This resembles the ideas of Kekule who saw benzene as cyclohexatriene.

http://www.dnatube.com/video/1421/Benz ene-Resonance-with-Pi-bonds
This is an attempt to demonstrate the modern theories of delocalisation of p orbitals.

Structure of Benzene

Aim: To compare the Kekul and delocalised models for benzene in terms of porbital overlap forming bonds. To review the evidence for a delocalised model of benzene in terms of bond lengths, enthalpy change of hydrogenation and resistance to reaction.

Kekul Structure Molecular formula: C6H6 Empirical formula CH

 The Kekul structure is actually cyclohexa-1,3,5 triene. Suggests 3 single and 3 double bonds. Should behave like cyclohexene and undergo ELECTROPHILIC ADDITION. Should have long, single bonds alternating with shorter double bonds.

Faults in Kekuls Model

Structure is regular hexagon with all 6 C-C bonds equal length 140 pm. This lies between C-C single bond length 154 pm and C=C double bond length 134 pm. (pm = picometre = 10-12 m.) Benzene does NOT behave like an alkene since it undergoes ELECTROPHILIC SUBSTITUTION.

Enthalpy Change of Hydrogenation Unsaturated compounds undergo ELECTROPHILIC ADDITION with hydrogen, under pressure with a nickel catalyst. C2H4 + H2 C2H6

Bonds broken = 1 C=C + 1 H-H Bonds made = 1 C-C + 2 C-H Enthalpy change of hydrogenation should be about -120kJmol-1

 Since benzene has 3 C=C bonds the enthalpy change of hydrogenation should be about -360 kJmol-1. Experimental data shows it to be 208kJmol-1. Conclusion: The ring does NOT contain C=C bonds and is more stable than expected. Benzene is about 150 kJ mol-1 MORE STABLE than Kekul structure.

Stabilisation Energy
The 150 kJ of energy is sometimes described as Stabilisation Energy. LESS energy is given out when benzene is hydrogenated than expected so benzene is MORE STABLE than expected and needs MORE ENERGY than expected to break the ring.

Resonance hybrid model of benzene.

This is not a reversible reaction. It is showing a cross between the 2 structures with each C-C bond having some C-C single and some C=C double bond character.

Displayed structure of benzene in which 6 electrons are delocalised and represented by a circle.

Skeletal Formula for Benzene

Molecular Orbital Model For Benzene

Orbital Overlap Model of Benzene

Each carbon in the hexagonal ring is sp2 hybridised . The C-H bonds are sigma bonds formed by the overlap of hydrogen 1s atomic orbital with a carbon sp2 hybrid orbital. Each C-C bond is a sigma bond with overlapping sp2 hybridised orbitals. Each H-C-C angle is 120o.The ring is planar. Each C has an unhybridised p orbital at 90o to the ring. These overlap laterally and form a delocalised orbital above and below the plane of the ring.

Molecular Orbitals For Benzene