NEET 2026
- Exam
- NEET
- Year
- 2026
- Subject
- Chemistry
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- Chapter
NEET 2026 · Chemistry · Chapter
The figure below shows four different substituted aryl halides...
The figure below shows four different substituted aryl halides labeled P, Q, R, and S.
These compounds undergo nucleophilic aromatic substitution when heated with aqueous NaOH. The reaction proceeds via an addition-elimination mechanism involving a carbanion intermediate. Identify the correct decreasing order of reactivity for these compounds towards this reaction.
Options
- AQ > S > P > R
- BQ > S > R > P
- CR > P > S > Q
- DS > Q > P > R
Correct answer
A. Q > S > P > R
Step-by-step solution
Nucleophilic aromatic substitution () proceeds via an addition-elimination mechanism, forming a carbanion intermediate (Meisenheimer complex) in the rate-determining step.
The reactivity of aryl halides towards increases with the presence of electron-withdrawing groups (EWGs) at the ortho and para positions, as they stabilize the carbanion intermediate through and effects. Conversely, electron-donating groups (EDGs) destabilize the intermediate and decrease reactivity.
Analyzing the given compounds:
Compound Q (1-chloro-2,4-dinitrobenzene) has two strong EWGs () at ortho and para positions, providing maximum stabilization to the intermediate. Thus, it is the most reactive.
Compound S (1-chloro-4-nitrobenzene) has one group at the para position, making it more reactive than unsubstituted chlorobenzene.
Compound P (chlorobenzene) has no substituents on the ring.
Compound R (1-chloro-4-methoxybenzene) has an group at the para position. The group is an EDG due to its strong effect, which destabilizes the carbanion intermediate, making it the least reactive.
Therefore, the decreasing order of reactivity is Q > S > P > R.
Answer: Q > S > P > R
The reactivity of aryl halides towards increases with the presence of electron-withdrawing groups (EWGs) at the ortho and para positions, as they stabilize the carbanion intermediate through and effects. Conversely, electron-donating groups (EDGs) destabilize the intermediate and decrease reactivity.
Analyzing the given compounds:
Compound Q (1-chloro-2,4-dinitrobenzene) has two strong EWGs () at ortho and para positions, providing maximum stabilization to the intermediate. Thus, it is the most reactive.
Compound S (1-chloro-4-nitrobenzene) has one group at the para position, making it more reactive than unsubstituted chlorobenzene.
Compound P (chlorobenzene) has no substituents on the ring.
Compound R (1-chloro-4-methoxybenzene) has an group at the para position. The group is an EDG due to its strong effect, which destabilizes the carbanion intermediate, making it the least reactive.
Therefore, the decreasing order of reactivity is Q > S > P > R.
Answer: Q > S > P > R