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Phenols are more acidic than alcohols because
- a)phenoxide ion is stabilised by resonance
- b)phenols are more soluble in polar solvents
- c)phenoxide ions do not exhibit resonance
- d)Alcohols do not lose H atoms at all.
Correct answer is option 'A'. Can you explain this answer?
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Phenols are more acidic than alcohols becausea) ...
Stabilization by Resonance:
- The main reason phenols are more acidic than alcohols is that the phenoxide ion formed after deprotonation of a phenol is stabilized by resonance.
- In phenols, the lone pair on oxygen can delocalize into the aromatic ring, creating a resonance structure where the negative charge is shared between the oxygen and the carbon atoms.
- This delocalization of charge stabilizes the phenoxide ion, making it more favorable for the phenol to lose a proton and form the phenoxide ion.
Solubility in Polar Solvents:
- While solubility in polar solvents is a property of phenols, it is not the main reason for their increased acidity compared to alcohols.
- The ability of phenols to form hydrogen bonds with polar solvents contributes to their solubility in such solvents but does not directly impact their acidity.
Non-Exhibition of Resonance in Phenoxide Ions:
- It is incorrect to say that phenoxide ions do not exhibit resonance. In fact, the resonance stabilization of the phenoxide ion is a key factor in the increased acidity of phenols compared to alcohols.
- The ability of the negative charge in the phenoxide ion to delocalize and stabilize across the aromatic ring is a crucial aspect of the acidity of phenols.
Lack of Hydrogen Atom Loss in Alcohols:
- The statement that alcohols do not lose hydrogen atoms at all is inaccurate. Alcohols can undergo deprotonation to form alkoxide ions, but the resulting alkoxide ions are not as stabilized as phenoxide ions due to the lack of resonance in alcohols.
- The main reason phenols are more acidic than alcohols is that the phenoxide ion formed after deprotonation of a phenol is stabilized by resonance.
- In phenols, the lone pair on oxygen can delocalize into the aromatic ring, creating a resonance structure where the negative charge is shared between the oxygen and the carbon atoms.
- This delocalization of charge stabilizes the phenoxide ion, making it more favorable for the phenol to lose a proton and form the phenoxide ion.
Solubility in Polar Solvents:
- While solubility in polar solvents is a property of phenols, it is not the main reason for their increased acidity compared to alcohols.
- The ability of phenols to form hydrogen bonds with polar solvents contributes to their solubility in such solvents but does not directly impact their acidity.
Non-Exhibition of Resonance in Phenoxide Ions:
- It is incorrect to say that phenoxide ions do not exhibit resonance. In fact, the resonance stabilization of the phenoxide ion is a key factor in the increased acidity of phenols compared to alcohols.
- The ability of the negative charge in the phenoxide ion to delocalize and stabilize across the aromatic ring is a crucial aspect of the acidity of phenols.
Lack of Hydrogen Atom Loss in Alcohols:
- The statement that alcohols do not lose hydrogen atoms at all is inaccurate. Alcohols can undergo deprotonation to form alkoxide ions, but the resulting alkoxide ions are not as stabilized as phenoxide ions due to the lack of resonance in alcohols.
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Community Answer
Phenols are more acidic than alcohols becausea) ...
Explanation:
Resonance Stabilization:
- Phenols are more acidic than alcohols because the phenoxide ion formed after deprotonation of phenol is stabilized by resonance.
- In phenol, the lone pair on the oxygen atom can resonate between the oxygen atom and the benzene ring, leading to delocalization of the negative charge.
- This resonance stabilization makes the phenoxide ion more stable compared to the alkoxide ion formed from alcohol deprotonation.
Solubility in Polar Solvents:
- While solubility in polar solvents can influence acidity to some extent, it is not the primary reason for phenols being more acidic than alcohols.
- The main factor is the resonance stabilization of the phenoxide ion.
Non-Resonance of Phenoxide Ions:
- Contrary to option (c), phenoxide ions do exhibit resonance due to the delocalization of the negative charge over the oxygen atom and the benzene ring.
- This resonance stabilization is a key factor in making phenols more acidic than alcohols.
Loss of H Atoms in Alcohols:
- Alcohols can lose H atoms during deprotonation to form alkoxide ions, but the key difference lies in the stability of the resulting ions.
- Due to resonance stabilization, phenoxide ions are more stable than alkoxide ions, making phenols more acidic than alcohols.
Therefore, the correct answer is option 'A' as the resonance stabilization of the phenoxide ion is the primary reason for phenols being more acidic than alcohols.
Resonance Stabilization:
- Phenols are more acidic than alcohols because the phenoxide ion formed after deprotonation of phenol is stabilized by resonance.
- In phenol, the lone pair on the oxygen atom can resonate between the oxygen atom and the benzene ring, leading to delocalization of the negative charge.
- This resonance stabilization makes the phenoxide ion more stable compared to the alkoxide ion formed from alcohol deprotonation.
Solubility in Polar Solvents:
- While solubility in polar solvents can influence acidity to some extent, it is not the primary reason for phenols being more acidic than alcohols.
- The main factor is the resonance stabilization of the phenoxide ion.
Non-Resonance of Phenoxide Ions:
- Contrary to option (c), phenoxide ions do exhibit resonance due to the delocalization of the negative charge over the oxygen atom and the benzene ring.
- This resonance stabilization is a key factor in making phenols more acidic than alcohols.
Loss of H Atoms in Alcohols:
- Alcohols can lose H atoms during deprotonation to form alkoxide ions, but the key difference lies in the stability of the resulting ions.
- Due to resonance stabilization, phenoxide ions are more stable than alkoxide ions, making phenols more acidic than alcohols.
Therefore, the correct answer is option 'A' as the resonance stabilization of the phenoxide ion is the primary reason for phenols being more acidic than alcohols.
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Phenols are more acidic than alcohols becausea) phenoxide ion is stabilised by resonance b) phenols are more soluble in polar solvents c) phenoxide ions do not exhibit resonance d) Alcohols do not lose H atoms at all. Correct answer is option 'A'. Can you explain this answer?
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