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

**1. Draw resonance structure(s) for the following molecules.**

**a)** ![structure](attachment:a.jpg) 

A benzene ring bonded to a three-carbon chain with a carbonyl group (C=O) at the end of the chain. The oxygen atom in the carbonyl group has two lone pairs of electrons.

**b)** ![structure](attachment:b.jpg)

A molecule with a long conjugated π-system. It begins with a single bond to an isopropyl group, followed by a sequence of alternating single and double carbon-carbon bonds.

**c)** ![structure](attachment:c.jpg)

A benzene ring bonded to a two-carbon chain with a positive charge on the second carbon and a double bond following that carbon. The double bond is between the second and third carbon.

**d)** ![structure](attachment:d.jpg)

A six-membered carbon ring (cyclohexane) bonded to a two-carbon chain with a positive charge on the second carbon and a double bond following that carbon. The double bond is between the second and third carbon.

**Detailed Explanation of Diagrams:**

- **Diagram a):** The molecule features a benzene ring, making it an aromatic compound. An extended chain with a carbonyl group introduces π-π conjugation possibilities. The resonance structures will be possible by delocalizing the electrons on the oxygen in the carbonyl group.
  
- **Diagram b):** This molecule has a conjugated diene system with isopropyl substitution. This type of conjugation can stabilize the molecule through delocalization of π-electrons.
  
- **Diagram c):** This structure presents an aromatic benzene ring connected to a positively charged carbon next to a double-bonded carbon. The positive charge can induce shifts in the π-system, creating resonance forms.

- **Diagram d):** The cyclohexane ring conjugated with a positively charged carbon. The presence of the double bond and positive charge suggests resonance stabilization through electron movement in the π-system.

These examples illustrate key principles in drawing and understanding resonance structures in organic compounds, which is central to grasping the behavior of complex molecules in different chemical environments.
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Transcribed Image Text:**Organic Chemistry: Resonance Structures** **1. Draw resonance structure(s) for the following molecules.** **a)** ![structure](attachment:a.jpg) A benzene ring bonded to a three-carbon chain with a carbonyl group (C=O) at the end of the chain. The oxygen atom in the carbonyl group has two lone pairs of electrons. **b)** ![structure](attachment:b.jpg) A molecule with a long conjugated π-system. It begins with a single bond to an isopropyl group, followed by a sequence of alternating single and double carbon-carbon bonds. **c)** ![structure](attachment:c.jpg) A benzene ring bonded to a two-carbon chain with a positive charge on the second carbon and a double bond following that carbon. The double bond is between the second and third carbon. **d)** ![structure](attachment:d.jpg) A six-membered carbon ring (cyclohexane) bonded to a two-carbon chain with a positive charge on the second carbon and a double bond following that carbon. The double bond is between the second and third carbon. **Detailed Explanation of Diagrams:** - **Diagram a):** The molecule features a benzene ring, making it an aromatic compound. An extended chain with a carbonyl group introduces π-π conjugation possibilities. The resonance structures will be possible by delocalizing the electrons on the oxygen in the carbonyl group. - **Diagram b):** This molecule has a conjugated diene system with isopropyl substitution. This type of conjugation can stabilize the molecule through delocalization of π-electrons. - **Diagram c):** This structure presents an aromatic benzene ring connected to a positively charged carbon next to a double-bonded carbon. The positive charge can induce shifts in the π-system, creating resonance forms. - **Diagram d):** The cyclohexane ring conjugated with a positively charged carbon. The presence of the double bond and positive charge suggests resonance stabilization through electron movement in the π-system. These examples illustrate key principles in drawing and understanding resonance structures in organic compounds, which is central to grasping the behavior of complex molecules in different chemical environments.
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