Diazomethane Resonance: Lewis Structure Soln

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In summary, the acceptable Lewis structure for Diazomethane is B, as it follows the octet rule with 4 bonds and 1 lone pair on each nitrogen. The incorrect resonance structures are C and D. While nitrogen is more electronegative than carbon, it can still have 4 bonds and a lone pair, contrary to what is stated in the Wikipedia article on the octet rule.
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runningman19
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Homework Statement


Which is an acceptable Lewis structure for Diazomethane?

Homework Equations


None

The Attempt at a Solution


The answer cannot be C or D, as both of these resonance structures are incorrect. I thought the answer was A, given that nitrogen is more electronegative than carbon, which would mean that a negative formal charge is more stable on nitrogen. This is not the case, the answer is actually B.
 

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  • #2
Count the electrons around each nitrogen in A.
 
  • #3
It has 4 bonds and 1 lone pair. I believe that I read somewhere that nitrogen cannot have 4 bonds and a lone pair. Is that correct?
 

1. What is the Lewis structure of diazomethane?

The Lewis structure of diazomethane, also known as CH2N2, is a linear molecule with a central carbon atom bonded to two nitrogen atoms. The carbon atom has two single bonds and one double bond, while each nitrogen atom has a single bond and a lone pair of electrons.

2. What is the resonance structure of diazomethane?

Diazomethane has two resonance structures, where the double bond can shift between the carbon and nitrogen atoms. This results in a delocalization of electrons and makes both structures equally valid representations of the molecule.

3. How do you draw the Lewis structure of diazomethane?

To draw the Lewis structure of diazomethane, start by placing the atoms in a linear arrangement. Then, determine the total number of valence electrons by adding the valence electrons of each atom. Next, fill the outer shells of the atoms with electrons, starting with the terminal atoms and then the central atom. Finally, check the octet rule to ensure that all atoms have a full outer shell. If not, use multiple bonds to complete the octet.

4. What is the significance of the resonance structure of diazomethane?

The resonance structure of diazomethane is significant because it explains the delocalization of electrons in the molecule. This means that the electrons are not localized to a specific bond, but rather spread out over the entire molecule. This delocalization increases the stability of the molecule.

5. How is the Lewis structure of diazomethane related to its properties?

The Lewis structure of diazomethane is related to its properties in several ways. The double bond between the carbon and nitrogen atoms makes the molecule highly reactive, and the delocalization of electrons makes it unstable. This instability is what makes diazomethane a useful reagent in organic synthesis, as it can easily undergo reactions to form new compounds.

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