ABSTRACT

Benzene is uniquely stable for a conjugated triene. This unique stability of benzene is given the identifying term: aromaticity. Benzene reacts by substitution, rather than addition like other alkenes, and does not readily undergo hydrogenation. Aromatic molecules are those that exhibit unique stability like benzene and follow a set of common characteristics: a planar molecule with a ring that has no sp3-hybridized atoms in the ring and there are 4n+2 π electrons. Molecules that do not fulfil these criteria are nonaromatic. A special type of nonaromatic molecules are those that otherwise fulfil all criteria but have 4n π electrons. If fully conjugated these molecules would be exceptionally unstable (antiaromatic), and so these molecules distort into non-conjugated conformations and are therefore nonaromatic as well. Readers will also be introduced to benzene ring nomenclature and the chemistry of phenol (hydroxybenzene).