Methyl nitrate, \(\mathrm{CH}_{3} \mathrm{NO}_{3}\), is used as a rocket
propellant. The skeletal structure of the molecule is \(\mathrm{CH}_{3}
\mathrm{ONO}_{2}\). The N and three O atoms all lie in the same plane, but the
\(\mathrm{CH}_{3}\) group is not in the same plane as the \(\mathrm{NO}_{3}\)
group. The bond angle \(\mathrm{C}-\mathrm{O}-\mathrm{N}\) is \(105^{\circ},\) and
the bond angle \(\mathrm{O}-\mathrm{N}-\mathrm{O}\) is \(125^{\circ} .\) One
nitrogen-to-oxygen bond length is \(136 \mathrm{pm},\) and the other two are
\(126 \mathrm{pm}\)
(a) Draw a sketch of the molecule showing its geometric shape.
(b) Label all the bonds in the molecule as \(\sigma\) or \(\pi\), and indicate the
probable orbital overlaps involved.
(c) Explain why all three nitrogen-to-oxygen bond lengths are not the same.