Kaushal-Naina- project 1 (II)

Kaushal-Naina- project 1 (II) - Ashay Mehta Organic...

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Organic Chemistry II April 30, 2010 Project 1: Benzene or 1,3,5- Cyclohexatriene? In trying to understand the aromatic nature of these structures, it is important to understand the concept of aromaticity in general. Aromaticity, also known as cyclic delocalization and resonance is a chemical property in which a molecule exhibits a stronger stabilization than it would if it were just conjugated. Aromatic compounds consist of a ring of unsaturated bonds, lone pairs and/or empty orbitals. This is because electrons usually are permitted to freely circle the atoms, which alternate double and single bonds. Aromatic substances follow Huckel’s Rule, which states that the molecules have 4n+2 delocalized electrons. The six-membered carbon ring with alternating double and single bonds, the hexatriene structure that was developed by August Kekule, is very common in aromatic molecules. 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 and include a molecule like toluene. After determining the heats of formation for benzene and 1, 3, 5 cyclohexatriene we found the difference of these values to be -9.7027 kcal/mol and this value is known as the relaxation energy. When I compared the relaxation energy to the aromatic stabilization energy of the benzene which was 33 kcal/mole that geometry does indeed Structure Heats of Formation
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Kaushal-Naina- project 1 (II) - Ashay Mehta Organic...

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