Question

Peroxypropionyl nitrate (PPN) is an eye irritant found in smog. Its skeleton structure is CC(C)(C)OCON(O)O (a) Draw the Lewis structure of PPN. (b) Indicate all the bond angles.

Short answer

Based on the Lewis structure and VSEPR theory, the bond angles in Peroxypropionyl nitrate (PPN) are as follows: - O-N-C: 107.3° - C-O-N: 104.5° - N=O and N-O: 120° - C-C and C-H: 109.5°.

Step-by-step solution

Write the molecular formula for PPN

The SMILES notation given is "CC(C)(C)OCON(O)O", which translates to the molecular formula C_5H_9NO_6.

Calculate the total number of valence electrons

We'll count the number of valence electrons in the PPN molecule: - Carbon (C): 5 atoms * 4 valence electrons = 20 e^- - Hydrogen (H): 9 atoms * 1 valence electron = 9 e^- - Nitrogen (N): 1 atom * 5 valence electrons = 5 e^- - Oxygen (O): 6 atoms * 6 valence electrons = 36 e^- Total number of valence electrons = 20 + 9 + 5 + 36 = 70 electrons

Drawing the Lewis structure

We'll start by arranging the atoms according to the given skeleton: CC(C)(C)OCON(O)O which corresponds to the parent structure: O || O - N - C - O - N - O || | C - H C | | H-C C-H | | H H Now we need to adjust the number of electrons to match the total number of valence electrons (70) by adding lone pairs. After adding the necessary lone pairs, the final Lewis structure is: O || O - N - C - O - N = O || | C - H C | | H-C C-H | | H H *Note: the double lines (||) represent double bonds. #b. Indicate all the bond angles#

Calculate the bond angles using VSEPR theory

Using the VSEPR (Valence Shell Electron Pair Repulsion) theory, we'll determine the geometry and bond angles for the central atoms in PPN: 1. O-N-C bond angle: - N has three bonding pairs (with O and C) and one lone pair. This corresponds to a trigonal pyramidal geometry. The ideal bond angle for a trigonal pyramidal is approximately 107.3°. 2. C-O-N bond angle: - O has two bonding pairs (with C and N) and two lone pairs. This corresponds to a bent geometry. The ideal bond angle for a bent geometry with two lone pairs is approximately 104.5°. 3. N=O and N-O bond angle: - N (in the nitrate group) has three bonding pairs (two with O and one with O) and one lone pair. This corresponds to a trigonal planar geometry. The ideal bond angle for a trigonal planar geometry is 120°. 4. C-C and C-H bond angles: - All the C atoms have three bonding pairs (either with C or H) and no lone pairs. This corresponds to a tetrahedral geometry. The ideal bond angle for a tetrahedral geometry is 109.5°. So, in summary, the bond angles for PPN are: - O-N-C: 107.3° - C-O-N: 104.5° - N=O and N-O: 120° - C-C and C-H: 109.5°.