Mehta-Ashay-244-Project2 - Ashay Mehta Organic Chemistry II...

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Ashay Mehta Organic Chemistry II April 30, 2010 Part I: Benzene or 1,3,5-Cyclohexatriene? When looking at these aromatic structures, it is important to understand the concept of aromaticity in general. Aromaticity is also known as cyclic delocalization. One of its biggest components is resonance which is a chemical property in which a molecule exhibits a stronger stabilization than it would is the molecule was conjugated. Aromatic compounds have a ring of either unsaturated bonds, lone pairs and/or empty orbitals. This is because electrons usually can freely circle the atoms, which alternate single bonds and double bonds. Aromatic substances follow Huckel’s Rule, which states that the molecules have 4n+2 delocalized electrons. Also, the molecule must be planar and every atom in the ring must have a p-orbital which overlaps with p-orbitals on either side. In general, benzene and most of its derivatives are aromatic compounds such as toluene. After determining the heats of formation for 1, 3, 5 cyclohexatriene and benzene, we found the difference of these values to be -9.7027 kcal/mol and this value is also called the relaxation energy. The comparison between the relaxation energy and the aromatic stabilization energy of the benzene which was 33 kcal/mole shows that Structure Heats of Formation (kcal/mol) Relative Heat of Formation (kcal/mol) Benzene 23.2403 kcal/mol 0 1,3,5-Cyclohexatriene 32.9230 kcal/mol 9.7027 Relaxation Energy -9.7027 kcal/mol
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geometry does indeed plays a vital role in the stabilization of benzene. While comparing
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Mehta-Ashay-244-Project2 - Ashay Mehta Organic Chemistry II...

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