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Aldol additions and condensations can also be catalyzed by aqueous acid. Write the mechanism for formation of an enol intermediate in the reaction of butanone with aqueous acid (such as dilute H₂SO4 or just H₂O¹). GHz 'Ht ay R 120 FI20

Aldol additions and condensations can also be catalyzed by aqueous acid. Write the mechanism for formation of an enol intermediate in the reaction of butanone with aqueous acid (such as dilute H₂SO4 or just H₂O¹). GHz 'Ht ay R 120 FI20

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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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**Aldol Additions and Condensations Catalyzed by Aqueous Acid** Aldol additions and condensations can also be catalyzed by aqueous acid. Below is the mechanism for the formation of an enol intermediate in the reaction of butanone with aqueous acid (such as dilute H₂SO₄ or just H₃O⁺). ### Reaction Mechanism Steps: 1. **Protonation of Carbonyl Oxygen:** - A proton (H⁺) from the acid adds to the carbonyl oxygen of butanone, creating a positively charged oxonium ion. 2. **Formation of the Enol:** - The alpha carbon adjacent to the carbonyl group donates a hydrogen, forming a double bond between the alpha carbon and the carbonyl carbon, resulting in the enol structure. Water is involved in the deprotonation step, essentially capturing the acidic hydrogen and stabilizing the structure. 3. **Resonance Stabilization:** - The newly formed double bond between the alpha carbon and the carbonyl carbon shows resonance with the remaining lone pair on the oxygen making the double bond flexible. The diagram illustrates butanone undergoing an acid-catalyzed transformation to create an enol intermediate through a series of protonation and deprotonation steps, demonstrating the movement of electrons and structural changes occurring at each stage. Understanding these transformations is critical for mastering complex reactions involving carbonyl chemistry in organic synthesis.
Transcribed Image Text:**Aldol Additions and Condensations Catalyzed by Aqueous Acid** Aldol additions and condensations can also be catalyzed by aqueous acid. Below is the mechanism for the formation of an enol intermediate in the reaction of butanone with aqueous acid (such as dilute H₂SO₄ or just H₃O⁺). ### Reaction Mechanism Steps: 1. **Protonation of Carbonyl Oxygen:** - A proton (H⁺) from the acid adds to the carbonyl oxygen of butanone, creating a positively charged oxonium ion. 2. **Formation of the Enol:** - The alpha carbon adjacent to the carbonyl group donates a hydrogen, forming a double bond between the alpha carbon and the carbonyl carbon, resulting in the enol structure. Water is involved in the deprotonation step, essentially capturing the acidic hydrogen and stabilizing the structure. 3. **Resonance Stabilization:** - The newly formed double bond between the alpha carbon and the carbonyl carbon shows resonance with the remaining lone pair on the oxygen making the double bond flexible. The diagram illustrates butanone undergoing an acid-catalyzed transformation to create an enol intermediate through a series of protonation and deprotonation steps, demonstrating the movement of electrons and structural changes occurring at each stage. Understanding these transformations is critical for mastering complex reactions involving carbonyl chemistry in organic synthesis.
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