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Chemistry
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...
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**Educational Content: Resonance Structures of Acetone Enolate** In organic chemistry, understanding the concept of resonance structures is essential for grasping how electrons are distributed in molecules. This example illustrates the resonance structures of the acetone enolate ion. ### Resonance Structures of Acetone Enolate #### Top Diagram: **Left Structure:** This structure depicts an enolate form of acetone. It shows a carbon-carbon double bond adjacent to a negatively charged oxygen atom with lone pairs of electrons. The negative charge indicates an excess electron density on the oxygen atom. **Right Structure:** This resonance form shows the distribution of the negative charge. Here, the double bond between the carbons has shifted, resulting in a single bond between the carbons and a double bond between the central carbon and oxygen. The oxygen atom now carries a negative formal charge, while the adjacent carbon holds a positive formal charge. These two structures are connected by a double-headed resonance arrow, indicating that the true nature of the acetone enolate ion is a hybrid of these two contributors. ### Description of the Bottom Image **Diagram:** The bottom image replicates the enolate form of acetone, illustrating one of the resonance structures identical to the left structure in the top diagram. It effectively shows the negative charge on the oxygen, the carbon-carbon double bond adjacent to it, and the position of the hydrogen atoms. #### Explanation of Resonance: These structures demonstrate the resonance delocalization of the negative charge. In the actual molecule, the electron density is not confined to one position but is instead shared across the structure, making the molecule more stable than any individual resonance form. This concept is crucial for understanding the reactivity and stability of enolates and other resonance-stabilized intermediates in organic reactions.
Transcribed Image Text:**Educational Content: Resonance Structures of Acetone Enolate** In organic chemistry, understanding the concept of resonance structures is essential for grasping how electrons are distributed in molecules. This example illustrates the resonance structures of the acetone enolate ion. ### Resonance Structures of Acetone Enolate #### Top Diagram: **Left Structure:** This structure depicts an enolate form of acetone. It shows a carbon-carbon double bond adjacent to a negatively charged oxygen atom with lone pairs of electrons. The negative charge indicates an excess electron density on the oxygen atom. **Right Structure:** This resonance form shows the distribution of the negative charge. Here, the double bond between the carbons has shifted, resulting in a single bond between the carbons and a double bond between the central carbon and oxygen. The oxygen atom now carries a negative formal charge, while the adjacent carbon holds a positive formal charge. These two structures are connected by a double-headed resonance arrow, indicating that the true nature of the acetone enolate ion is a hybrid of these two contributors. ### Description of the Bottom Image **Diagram:** The bottom image replicates the enolate form of acetone, illustrating one of the resonance structures identical to the left structure in the top diagram. It effectively shows the negative charge on the oxygen, the carbon-carbon double bond adjacent to it, and the position of the hydrogen atoms. #### Explanation of Resonance: These structures demonstrate the resonance delocalization of the negative charge. In the actual molecule, the electron density is not confined to one position but is instead shared across the structure, making the molecule more stable than any individual resonance form. This concept is crucial for understanding the reactivity and stability of enolates and other resonance-stabilized intermediates in organic reactions.
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