Textbook Question
Draw all possible resonance structures for the reactive intermediates shown.
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1. A Review of General Chemistry
Resonance Structures
3:17 minutesProblem 17
Textbook Question
Use resonance forms to show delocalization of the negative charge in the Ruhemann's purple anion.
Verified step by step guidance1
Identify the location of the negative charge in the Ruhemann's purple anion. In the given structures, the negative charge is located on the oxygen atom of the carbonyl group.
Recognize that resonance involves the delocalization of electrons, particularly the negative charge, across the molecule. This can occur through the pi system of the aromatic rings and the carbonyl groups.
Begin by moving the lone pair of electrons from the negatively charged oxygen to form a double bond with the adjacent carbon, pushing the pi electrons of the existing carbonyl double bond onto the oxygen atom, creating a new resonance structure.
Continue the process of electron delocalization by moving the pi electrons from the newly formed double bond into the aromatic ring, allowing the negative charge to be distributed across the ring system. This can be repeated to show the charge delocalization through the entire conjugated system.
Draw all possible resonance structures, ensuring that each structure maintains the overall charge of the molecule and follows the rules of resonance, such as maintaining the octet rule for second-row elements and minimizing charge separation.
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3mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Resonance
Resonance in organic chemistry refers to the delocalization of electrons across adjacent atoms, allowing for multiple valid Lewis structures. These structures, known as resonance forms, depict the same molecule with different electron arrangements. Resonance stabilizes molecules by distributing charge and electron density, as seen in Ruhemann's purple anion, where the negative charge is spread across the molecule.
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Delocalization of Charge
Delocalization of charge involves the spreading of electron density over several atoms, reducing the energy and increasing the stability of the molecule. In Ruhemann's purple anion, the negative charge is not confined to a single atom but is distributed across the structure, as shown in the resonance forms. This delocalization is crucial for understanding the stability and reactivity of the anion.
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Anion Stability
Anion stability is influenced by factors such as resonance, electronegativity, and the ability to delocalize charge. In Ruhemann's purple anion, the stability is enhanced by resonance, which allows the negative charge to be shared among multiple atoms. This distribution reduces the potential energy and makes the anion less reactive, highlighting the importance of resonance in stabilizing charged species.
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