Chapter 14, Problem 14.47P

Interpretation Introduction

(a)

Interpretation:

Why ${\text{C}}_8{\text{H}}_{\text{8}}{}^{\text{2-}}$ ion is easy to make via redox reaction, if cyclooctatetraene is treated with potassium, is to be explained.

Concept introduction:

Organic compounds that are not aromatic are comparatively less stable than aromatic compounds.

Huckel’s rule for aromaticity states that if a species possesses a pi system of molecular orbitals constructed from p-orbitals that are fully conjugated around a ring (${\text{sp}}^2$ hybridized), then the species is aromatic if the number of electrons in that $\text{π}$- system is either $2,6,10,14,1,\text{and so on}\text{.}$

Interpretation Introduction

(b)

Interpretation:

Geometry of the dianion ${\text{C}}_8{\text{H}}_{\text{8}}{}^{\text{2-}}$ is to be explained.

Concept introduction:

Aromatic compounds are chemical compounds that contain conjugated planar ring systems with delocalized pi electron clouds instead of discrete alternating single and double bonds.