Question

Explain why is ortho nitrophenol more acidic than ortho methoxyphenol?

Solution
Verified by Toppr

In ortho nitro phenol, electron withdrawing nitro group is present in ortho position, the electron density of OH bond is reduced.
This makes removal of proton easy. After deprotonation, o-nitrophenoxide ion is resonance stabilized. Hence, ortho nitrophenol is a stronger acid.
In ortho methoxyphenol, electron releasing methoxy group is present in ortho position, the electron density of OH bond is increased.
This makes removal of proton difficult. Hence, ortho methoxyphenol is less acidic.

Was this answer helpful?
7
Similar Questions
Q1

Explain why p-nitrophenol is more acidic than phenol?

View Solution
Q2

Ortho and para nitrophenols are more acidic than phenol. Draw the resonance structures of the corresponding phenoxide ions.

View Solution
Q3

Explain why is ortho nitrophenol more acidic than ortho methoxyphenol?

View Solution
Q4

Explain the following behaviours.
(i) Alcohols are more soluble in water than the hydrocarbons of comparable molecular masses.
(ii) Ortho-nitrophenol is more acidic than ortho-methoxyphenol.

View Solution
Q5

Why ortho-Nitrophenol is steam volatile while para-Nitrophenol is less volatile?

View Solution
Solve
Guides