Question

Draw all possible lewis structures (including resonance structures for methyl azide (ch3n3 using lewis structure rules. One or more of your structures may seem unstable or unlikely; include them in your answer as long as they do not violate lewis structure rules. For each resonance structure, assign formal charges to all atoms that have formal charge. Draw all possible lewis dot structure for methyl azide. Include all hydrogen atoms and nonbonding electrons. Show the formal charges of all atoms

Answer 1

Methyl azide (CH3N3) has three possible Lewis structures, as shown below:

Structure 1:
H
|
H - C = N
|
N
|
N

Structure 2:
H
|
H - C ≡ N
|
N
|
N

Structure 3:
H
|
H - C ≡ N+
|
N-
|
N

In Structure 1, there is a double bond between the central carbon atom and one of the nitrogen atoms, and a single bond between the central carbon atom and the other nitrogen atom. In Structure 2, there is a triple bond between the central carbon atom and one of the nitrogen atoms, and a single bond between the central carbon atom and the other nitrogen atom. In Structure 3, there is a triple bond between the central carbon atom and the positively charged nitrogen atom, and a single bond between the central carbon atom and the negatively charged nitrogen atom.

All three structures satisfy the octet rule for all atoms and obey the Lewis structure rules.

For resonance structures, we can observe that Structures 1 and 2 are actually resonance structures of each other, as the double and triple bonds can be interchanged without violating any valence electron rules. Therefore, we can draw a hybrid structure that represents the average of these two resonance structures:

Hybrid Structure:
H
|
H - C = N ⇌ H - C ≡ N
|
N
|
N

In this hybrid structure, the double and triple bonds have equal bond order and the formal charges on all atoms are as follows:

Carbon: 0
Nitrogen (single bond): 0
Nitrogen (double/triple bond): 0
Hydrogen: +1

Note that the formal charge on the carbon atom is zero in all structures, and the formal charges on the nitrogen and hydrogen atoms are all either zero or +1, which are the most stable formal charges for these atoms.