One of the following structures for nitrobenzene is not a significant resonance contributor. Circle the structure that is not a significant resonance contributor.

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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One of the following structures for nitrobenzene is not a significant resonance contributor. Circle the structure that is not a significant resonance contributor. 

The image depicts the resonance structures of the nitrobenzene molecule. 

**Description of Structures:**

1. **Left Structure:**
   - A benzene ring is bonded to a nitro group (NO₂).
   - The nitrogen atom (N) is positively charged and forms a double bond with one oxygen atom and a single bond with the other oxygen atom.
   - The oxygen with the single bond has two lone pairs and a negative charge.

2. **Middle Structure:**
   - Similar to the left structure, but the double bond alternates to the other oxygen atom.
   - Again, the nitrogen atom is positively charged, and the negative charge is now on the oxygen atom with the double bond from the left structure.

3. **Right Structure:**
   - The nitrogen is still positively charged, showing a coordinate covalent bond with both oxygens as single bonds, balancing the charges across the nitro group.
   - Each oxygen atom has three lone pairs, with one oxygen displaying a formal charge.

**Explanation:**

These resonance forms illustrate the delocalization of electrons in the nitrobenzene molecule. The double-headed arrows indicate that the true structure is a hybrid of the depicted resonance forms, which stabilizes the molecule by distributing charge over different atoms in the structure. Each form represents a different potential arrangement of electrons within the molecule.
Transcribed Image Text:The image depicts the resonance structures of the nitrobenzene molecule. **Description of Structures:** 1. **Left Structure:** - A benzene ring is bonded to a nitro group (NO₂). - The nitrogen atom (N) is positively charged and forms a double bond with one oxygen atom and a single bond with the other oxygen atom. - The oxygen with the single bond has two lone pairs and a negative charge. 2. **Middle Structure:** - Similar to the left structure, but the double bond alternates to the other oxygen atom. - Again, the nitrogen atom is positively charged, and the negative charge is now on the oxygen atom with the double bond from the left structure. 3. **Right Structure:** - The nitrogen is still positively charged, showing a coordinate covalent bond with both oxygens as single bonds, balancing the charges across the nitro group. - Each oxygen atom has three lone pairs, with one oxygen displaying a formal charge. **Explanation:** These resonance forms illustrate the delocalization of electrons in the nitrobenzene molecule. The double-headed arrows indicate that the true structure is a hybrid of the depicted resonance forms, which stabilizes the molecule by distributing charge over different atoms in the structure. Each form represents a different potential arrangement of electrons within the molecule.
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