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Problem 2 A nitro group (-NO₂) effectively stabilizes a negative charge on an adjacent carbon atom through resonance: R. R. R R OH minor major Two of the following nitrophenols are much more acidic than phenol itself. The third compound is only slightly more acidic than phenol. Use resonance structures of the appropriate phenoxide ions to show why two of these anions should be unusually stable. a NO₂ minor 2-nitrophenol OH NO₂ 3-nitrophenol R. O₂N R OH 4-nitrophenol

Problem 2 A nitro group (-NO₂) effectively stabilizes a negative charge on an adjacent carbon atom through resonance: R. R. R R OH minor major Two of the following nitrophenols are much more acidic than phenol itself. The third compound is only slightly more acidic than phenol. Use resonance structures of the appropriate phenoxide ions to show why two of these anions should be unusually stable. a NO₂ minor 2-nitrophenol OH NO₂ 3-nitrophenol R. O₂N R OH 4-nitrophenol

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter2: Polar Covalent Bonds; Acids And Bases
Section2.SE: Something Extra
Problem 25MP: Use curved arrows to draw the protonated form of each Lewis base below.
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### Problem 2 A nitro group (–NO₂) effectively stabilizes a negative charge on an adjacent carbon atom through resonance: Structure showing resonance forms: - The resonance structures depict a series of double-headed arrows indicating the shifting of electrons between different forms. - In the first minor form, the nitro group is attached to an alkyl group (R), with a carbon double-bonded to an oxygen, holding a negative charge. - This resonates to a second form (also labeled as minor), where the electron shifts towards the nitrogen of the nitro group. - The major resonance form shows a fully stabilized structure where the negative charge is delocalized over the nitro group. ### Text Description Two of the following nitrophenols are much more acidic than phenol itself. The third compound is only slightly more acidic than phenol. Use resonance structures of the appropriate phenoxide ions to show why two of these anions should be unusually stable. ### Chemical Structures: 1. **2-Nitrophenol:** - Structure: A benzene ring with an OH group (hydroxyl) attached to the first carbon and a NO₂ group attached to the second carbon. 2. **3-Nitrophenol:** - Structure: A benzene ring with an OH group attached to the first carbon and a NO₂ group attached to the third carbon. 3. **4-Nitrophenol:** - Structure: A benzene ring with an OH group attached to the first carbon and a NO₂ group attached to the fourth carbon. The problem involves analyzing the resonance structures of these nitrophenols to explain their differing acidic strengths. The proximity of the nitro group to the hydroxyl group in the benzene ring affects the stability of the resulting phenoxide ion, thereby influencing the acidity of the compound.
Transcribed Image Text:### Problem 2 A nitro group (–NO₂) effectively stabilizes a negative charge on an adjacent carbon atom through resonance: Structure showing resonance forms: - The resonance structures depict a series of double-headed arrows indicating the shifting of electrons between different forms. - In the first minor form, the nitro group is attached to an alkyl group (R), with a carbon double-bonded to an oxygen, holding a negative charge. - This resonates to a second form (also labeled as minor), where the electron shifts towards the nitrogen of the nitro group. - The major resonance form shows a fully stabilized structure where the negative charge is delocalized over the nitro group. ### Text Description Two of the following nitrophenols are much more acidic than phenol itself. The third compound is only slightly more acidic than phenol. Use resonance structures of the appropriate phenoxide ions to show why two of these anions should be unusually stable. ### Chemical Structures: 1. **2-Nitrophenol:** - Structure: A benzene ring with an OH group (hydroxyl) attached to the first carbon and a NO₂ group attached to the second carbon. 2. **3-Nitrophenol:** - Structure: A benzene ring with an OH group attached to the first carbon and a NO₂ group attached to the third carbon. 3. **4-Nitrophenol:** - Structure: A benzene ring with an OH group attached to the first carbon and a NO₂ group attached to the fourth carbon. The problem involves analyzing the resonance structures of these nitrophenols to explain their differing acidic strengths. The proximity of the nitro group to the hydroxyl group in the benzene ring affects the stability of the resulting phenoxide ion, thereby influencing the acidity of the compound.
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