Benzene and Aromaticity

Vocabulary

annulene

any of a class of completely conjugated cyclic hydrocarbons (such as benzene or cyclooctatetraene) that are monocyclic

antiaromatic

molecule that is cyclic, has a continuous circle of p orbitals, has planar geometry, and does not have a Hückel number of electrons but instead has [4n] π\pi electrons

aromatic

molecule that is cyclic, has a continuous circle of p orbitals, has planar geometry, and has a Hückel number (4n+24n+2) of π\pi electrons

benzene

cyclic aromatic molecule with the chemical formula C6H6

derivative

compound that is derived from a similar compound by a chemical reaction

disubstituted derivative

derivative of benzene with two substituents

Frost circles

method to predict bonding π\pi molecular orbitals, which indicate aromaticity

Hückel's rule

rule that states that the number of delocalized electrons in the π\pi cloud in an aromatic ring is equal to [4n+24n+2], where n is zero or a positive integer

heterocyclic

any molecule relating to, characterized by, or being a ring composed of atoms of more than one kind

infrared (IR) spectroscopy

method that observes the vibrations of bonds and provides evidence of the functional groups present

meta

prefix that indicates there is one carbon atom between the carbon atoms that have the substituents, producing a 1,3-disubstituted benzene pattern

molecular orbital theory

solution of the Schrödinger equation that describes the probable location of an electron relative to the nuclei in a molecule and so indicates the nature of any bond in which the electron is involved

monosubstituted derivative

derivative of benzene with only one substituent

nonaromatic

molecule is not cyclic or planar or does not have a continuous circle of p orbitals

ortho

prefix that indicates there are no carbon atoms between the carbon atoms that have the substituents, producing a 1,2-disubstituted benzene pattern

para

prefix that indicates there are two carbon atoms between the carbon atoms that have the substituents, producing a 1,4-disubstituted benzene pattern

polycyclic

refers to molecules with more than one ring structure

polycyclic aromatic compound

compound that has more than one ring structure and is aromatic

polysubstituted derivative

benzene with more than two substituents

resonance

method that organic chemists use to depict the Lewis structures of organic molecules where electrons can be in two or more different places around fixed atoms