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The increasing order of acidity among ph...

The increasing order of acidity among phenol, p-methylphenol, m-nitrophenol and p-nitrophenol is:

A

m-nitrophenol, p-nitrophenol, phenol, p-methylphenol

B

p-methylphenol, m-nitrophenol, phenol, p-nitrophenol

C

p-methylphenol, phenol, m-nitrophenol, p-nitrophenol

D

Phenol, p-methylphenol, p-nitrophenol, m-nitrophenol

Text Solution

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The correct Answer is:
To determine the increasing order of acidity among phenol, p-methylphenol, m-nitrophenol, and p-nitrophenol, we need to analyze the stability of their conjugate bases. The more stable the conjugate base, the stronger the acid. ### Step-by-Step Solution: 1. **Identify the Compounds:** - Phenol (C6H5OH) - p-Methylphenol (C6H4(CH3)OH) - m-Nitrophenol (C6H4(NO2)OH) - p-Nitrophenol (C6H4(NO2)OH) 2. **Understand Acidity and Conjugate Bases:** - Acidity is determined by the stability of the conjugate base formed after the acid donates a proton (H+). - For phenols, the conjugate base is formed by deprotonating the hydroxyl group (OH), resulting in a phenoxide ion (C6H5O−). 3. **Analyze Each Compound:** - **Phenol:** The phenoxide ion formed is stabilized by resonance. The negative charge on the oxygen can delocalize into the aromatic ring, making it relatively stable. - **p-Methylphenol:** The methyl group (CH3) is an electron-donating group (due to +I effect), which destabilizes the phenoxide ion by increasing electron density on the negatively charged oxygen. Thus, it is less acidic than phenol. - **m-Nitrophenol:** The nitro group (NO2) is an electron-withdrawing group, but because it is in the meta position, it does not effectively stabilize the negative charge on the oxygen through resonance. Therefore, it has moderate acidity. - **p-Nitrophenol:** The nitro group is in the para position, which allows it to stabilize the negative charge on the phenoxide ion through resonance. This makes p-nitrophenol more acidic than both phenol and m-nitrophenol. 4. **Rank the Acidity:** - p-Nitrophenol > m-Nitrophenol > Phenol > p-Methylphenol - Thus, the increasing order of acidity is: - p-Methylphenol < Phenol < m-Nitrophenol < p-Nitrophenol ### Final Answer: The increasing order of acidity is: **p-Methylphenol < Phenol < m-Nitrophenol < p-Nitrophenol**
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