"The presence of an electron-withdrawing group $\left( -NO_2 \right)$ at the ortho and para positions in haloarenes increases the reactivity of haloarenes towards nucleophilic substitution reactions." Prove this with an example.

Vedclass pdf generator app on play store
Vedclass iOS app on app store
(N/A) In haloarenes,the presence of an electron-withdrawing group like $-NO_2$ facilitates the nucleophilic substitution of the $-Cl$ atom by an $-OH$ group. The presence of $-NO_2$ groups at ortho and para positions stabilizes the carbanion intermediate through resonance,thereby increasing the reactivity towards $S_NAr$ reactions.
Example:
$1$. Chlorobenzene $(C_6H_5Cl)$ requires harsh conditions ($623 \ K$ and $300 \ atm$ pressure) for the substitution of $-Cl$ by $-OH$.
$2$. $p$-Nitrochlorobenzene $(p-NO_2C_6H_4Cl)$ requires milder conditions $(443 \ K)$ for the same substitution.
$3$. As the number of $-NO_2$ groups increases at ortho/para positions,the reaction conditions become even milder:
- With two $-NO_2$ groups ($2$,$4$-dinitrochlorobenzene),the reaction occurs at $368 \ K$.
- With three $-NO_2$ groups ($2$,$4$,$6$-trinitrochlorobenzene),the reaction occurs simply by warming with water.

Explore More

Similar Questions

Which of the following reactions is used to prepare toluene from bromobenzene?

Aryl halides are less reactive towards nucleophilic substitution reactions than alkyl halides because of:

Assertion : $S_{N}2$ reaction of an optically active aryl halide with an aqueous solution of $KOH$ always gives an alcohol with opposite sign of rotation.
Reason : $S_{N}2$ reactions always proceed with retention of configuration.

The major product of the following reaction will be:

Difficult
View Solution

For the given reaction,identify the major product $C$.

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