Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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**Resonance Structures in Organic Chemistry**

Consider the resonance scheme shown below. Select the correct answer from the list below.

**Resonance Structures:**

A ⇄ B ⇄ C

- **Structure A**:
  - Benzene ring with one double bond and an oxygen atom with two lone pairs and a positive charge.
  - One lone pair of electrons on the oxygen moves to form a double bond with the adjacent carbon, while the double bond between carbon and the other carbon shifts to form a double bond between the adjacent carbon atoms.

- **Structure B**: 
  - Benzene ring with a double bond between the oxygen and the carbon, and an extra single bond connected to a negatively charged carbon.
  - Double-headed arrow indicates resonance.
  - One of the lone pairs from the negatively charged carbon moves to form another double bond within the ring, the double bond between the ring carbon and the oxygen shifts to position the lone pairs back on the oxygen, giving it a positive charge.

- **Structure C**: 
  - Benzene ring with an oxygen atom having three lone pairs and no charge, while the neighboring carbon adopts the positive charge due to the shift of electrons.
  
**Possible Answers:**

1. Structure B is breaking the octet rule.
2. The charge on the carbons needs to be positive in structure C.
3. The charge on the oxygen of structure C is not positive.
4. This mechanism is free of errors.

### Diagram Explanation:

- **Diagram A**: 
  The arrow represents the movement of electrons to form resonance structure B. Specifically, one lone pair on the oxygen forms a double bond, and the existing double bond shifts to an adjacent position.

- **Diagram B**: 
  The double-headed arrows between structures indicate resonance. The negative charge on the carbon and the movement of these electrons forms the next resonance structure C by shifting bonds and charges in the ring.

- **Diagram C**: 
  In structure C, the oxygen atom holds a single bond with the adjacent carbon, while that carbon holds a positive charge due to the movement of electrons forming stable resonance structures within the compound.

Make sure to review such mechanisms to ensure accurate understanding of the resonance forms in organic molecules.

**Select the correct answer from the provided options.**
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Transcribed Image Text:**Resonance Structures in Organic Chemistry** Consider the resonance scheme shown below. Select the correct answer from the list below. **Resonance Structures:** A ⇄ B ⇄ C - **Structure A**: - Benzene ring with one double bond and an oxygen atom with two lone pairs and a positive charge. - One lone pair of electrons on the oxygen moves to form a double bond with the adjacent carbon, while the double bond between carbon and the other carbon shifts to form a double bond between the adjacent carbon atoms. - **Structure B**: - Benzene ring with a double bond between the oxygen and the carbon, and an extra single bond connected to a negatively charged carbon. - Double-headed arrow indicates resonance. - One of the lone pairs from the negatively charged carbon moves to form another double bond within the ring, the double bond between the ring carbon and the oxygen shifts to position the lone pairs back on the oxygen, giving it a positive charge. - **Structure C**: - Benzene ring with an oxygen atom having three lone pairs and no charge, while the neighboring carbon adopts the positive charge due to the shift of electrons. **Possible Answers:** 1. Structure B is breaking the octet rule. 2. The charge on the carbons needs to be positive in structure C. 3. The charge on the oxygen of structure C is not positive. 4. This mechanism is free of errors. ### Diagram Explanation: - **Diagram A**: The arrow represents the movement of electrons to form resonance structure B. Specifically, one lone pair on the oxygen forms a double bond, and the existing double bond shifts to an adjacent position. - **Diagram B**: The double-headed arrows between structures indicate resonance. The negative charge on the carbon and the movement of these electrons forms the next resonance structure C by shifting bonds and charges in the ring. - **Diagram C**: In structure C, the oxygen atom holds a single bond with the adjacent carbon, while that carbon holds a positive charge due to the movement of electrons forming stable resonance structures within the compound. Make sure to review such mechanisms to ensure accurate understanding of the resonance forms in organic molecules. **Select the correct answer from the provided options.**
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