
- A(b) < (a) < (c) < (d)
- B(a) < (b) < (c) < (d)
- C(b) < (a) < (d) < (c)
- D(a) < (b) < (d) < (c)
View written solutionFree
Correct answer: D
- Identify the compounds and the reaction trend
In nitration of aromatic amines/anilides, the rate depends on how strongly the substituent donates electron density to the benzene ring.
The usual order of activating effect is:
and free aniline in strongly acidic nitrating mixture is largely protonated to anilinium ion, so its ring becomes much less reactive.
- Key principle for each compound
-
Aniline in nitrating mixture gets protonated: This makes it least reactive toward electrophilic nitration.
-
Diphenylamine has the nitrogen lone pair shared with two phenyl rings, so donation to any one ring is less than in acetanilide, but it is still more activating than protonated aniline.
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Acetanilide has the group , which still donates by resonance to the ring and avoids strong protonation problems of aniline under nitration conditions. Hence it nitrates more easily than aniline and diphenylamine.
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N,N-dimethylaniline (if present among the figures) has a strongly electron-donating amino group, making the ring most activated toward nitration among these protected/unprotonation-comparable cases.
- Relative reactivity
Thus the increasing order is:
which corresponds to
- Match with options
This is Option D.
Final Answer
So, the correct option is D.
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