Explain why $ortho$-nitrophenol is more acidic than $ortho$-methoxyphenol?

Vedclass pdf generator app on play store
Vedclass iOS app on app store
The $-NO_2$ group is an electron-withdrawing group $(EWG)$ due to both $-I$ and $-M$ effects. The presence of this group at the $ortho$ position decreases the electron density in the $O-H$ bond,facilitating the release of a proton $(H^+)$.
Furthermore,the $o$-nitrophenoxide ion formed after the loss of the proton is significantly stabilized by resonance involving the nitro group.
On the other hand,the $-OCH_3$ group is an electron-releasing group $(ERG)$ due to its $+M$ effect. This increases the electron density in the $O-H$ bond,making it harder to release the proton.
Therefore,$ortho$-nitrophenol is a stronger acid than $ortho$-methoxyphenol.

Explore More

Similar Questions

The major product in the following reaction is:

Match the following $pKa$ values:
Acid$pKa$
$(a)$ Phenol$(i)$ $16$
$(b)$ $p$-Nitrophenol$(ii)$ $0.78$
$(c)$ Ethanol$(iii)$ $10$
$(d)$ Picric acid$(iv)$ $7.1$

The $IUPAC$ name of picric acid is

Which of the following phenols is isolated from the defensive secretion of grasshopper species?

Phenol is

Difficult
View Solution

Vedclass Products

For Students

Vedclass Test Series

Mock tests in real JEE/NEET style with performance analysis. 5-day free trial.

Start Free Trial
For Teachers

Exam Paper Generator

Generate Set A/B/C/D exam papers from 7.5L+ questions in 2 minutes. 3 chapters free.

Try Free
For Institutes

Online Exam Module

Live online exams with unlimited students, 360° analytics & white-label branding.

See Demo