SATHEE: Alcohols Phenols and Ethers

Alcohols Phenols and Ethers - Result Question 44

####45. Increasing order of acid strength among $p$ -methoxyphenol, $p$ -methylphenol and $p$ -nitrophenol is

[1993]

(a) $p$ -Nitrophenol, $p$ -Methoxyphenol, $p$ -Methylphenol

(b) $p$ -Methylphenol, $p$ -Methoxyphenol, $p$ -Nitrophenol

(d) p-Methoxyphenol, $p$ -Methylphenol, $p$ -Nitrophenol

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Solution:

(d) Electron-donating groups (- $O C H_{3}, - C H_{3}$ etc.) tend to decrease and electron withdrawing groups $(- N O_{2})$ tend to increase the acidic character of phenols. Since $- O C H_{3}$ is a more powerful electron-donating group than $- C H_{3}$ group, therefore, $p$ -methylphenol is slightly more acidic than $p$ -methoxyphenol while $p$ -nitrophenol is the strongest acid. Thus, option (d), i.e. p-methoxyphenol, $p$ -methylphenol, $p$ -nitrophenol is correct.

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Alcohols Phenols and Ethers - Result Question 44

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