Chapter 11, Problem 51IAE

Methyl nitrate, ${\text{CH}}_{\text{2}}{\text{NO}}_{\text{2}}$ , is used as a rocket propellant. The skeletal structure of the molecule is ${\text{CH}}_{\text{2}}{\text{ONO}}_{\text{2}}$_. The N and three O atoms all lie in the same plane, but the ${\text{CH}}_{\text{2}}$ group is not in the same plane as the ${\text{NO}}_{\text{2}}$ group. The bond angle C−O−N is 105^o, and the bond angle O−N−O is
125^o. One nitrogen-to-oxygen bond length is 136 pm, and the other two are 126 pm.

1. Draw a sketch of the molecule showing its geometric shape.

Label all the bonds in the molecule as or r, and indicate the probable orbital overlaps involved.

Explain why all three nitrogen-to-oxygen bond lengths are not the same.