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

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
icon
Concept explainers
Question

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.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps with 2 images

Blurred answer
Knowledge Booster
Electronic Effects
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY