Draw two bona fide Lewis resonance structures for methyl azide () showing all bonds & lone pairs and any formal charges (you can use partial structure below, which shows the bonding sequence, for the 1st one

Draw two bona fide Lewis resonance structures for methyl azide (
) showing all bonds & lone pairs and any formal charges (you can use partial structure below, which shows the bonding sequence, for the 1^st one):

5. Draw a second resonance structure for the reactive intermediate shown below: Show all valence electrons as bonds or lone pairs & indicate any formal charges.

The Correct Answer and Explanation is:

To draw two bona fide Lewis resonance structures for methyl azide (CH₃-N₃), let’s first understand the bonding sequence and the general structure.

Structure of Methyl Azide (CH₃-N₃):

Methyl azide consists of a methyl group (CH₃-) attached to a nitrogen group (N₃). The N₃ part has a linear arrangement, with a central nitrogen atom bonded to two other nitrogen atoms (one on each side).

The bonding sequence is:

• The central nitrogen atom in N₃ (the N attached to CH₃) is connected to the other two nitrogens.
• The central nitrogen atom will have lone pairs, while the nitrogens at the ends can have formal charges.

First Resonance Structure:

1. CH₃-N≡N⁻–N⁺:
   • The CH₃ group (methyl) is single-bonded to the central nitrogen (N).
   • The nitrogen attached to the CH₃ group (N) has a triple bond to the adjacent nitrogen atom (N).
   • The terminal nitrogen (on the far right) has a positive charge, and the adjacent nitrogen (on the left) has a negative charge.
   In this structure:
   • The central nitrogen has a lone pair.
   • The terminal nitrogen on the right side has a positive formal charge (+1).
   • The nitrogen on the left side has a negative formal charge (-1).

Second Resonance Structure:

2. CH₃-N⁺-N≡N⁻:
   • In this structure, the formal charges are swapped between the terminal nitrogens.
   • The nitrogen attached to the CH₃ group (N) has a positive formal charge.
   • The nitrogen on the far right is triple-bonded to the central nitrogen, while the nitrogen on the left has a negative charge.
   In this structure:
   • The central nitrogen (attached to CH₃) has a positive charge.
   • The nitrogen on the far left (N) has a negative formal charge.

Explanation of Resonance:

• Both resonance structures depict the same bonding arrangement, but the formal charges are redistributed. The two nitrogens at the ends of the N₃ group can each hold a formal charge in different configurations, contributing to the overall resonance hybrid.
• The total number of electrons and bonds remain the same in both structures.
• The formal charges are significant because they determine the reactivity of the molecule in different environments.

Conclusion:

These two structures are both valid representations of methyl azide, and the actual structure is a hybrid of both. The resonance structures help us understand how the molecule might behave, especially in reactions where electron distribution is important.