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With respect to electrophilic aromatic substitution, reactivity order of pyrrole, pyridine and indole is:
  • a)
    Indole > Pyrrole > Pyridine
  • b)
    Pyrrole > Pyridine > Indole
  • c)
    Pyrrole > Indole > Pyridine
  • d)
    Indole > Pyridine > Pyrrole 
Correct answer is option 'C'. Can you explain this answer?
Verified Answer
With respect to electrophilic aromatic substitution, reactivity order ...
The aromatic lone pair owing to nitrogen in pyrrole makes the aromatic system more electron rich, and you can get a hint of it by looking at the electron pushing mechanism there.

The electron pushing from pyridine fails, firstly because the lone pair is fixed at an orthogonal position away from the aromatic ring. Secondly, that particular intermmediate cannot be obtained because of structural geometry problems, (=N=)+ should be linear and cannot be formed while maintaining a ring.
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With respect to electrophilic aromatic substitution, reactivity order ...
Reactivity order of pyrrole, pyridine and indole with respect to electrophilic aromatic substitution is:

Pyrrole < indole="" />< />

Explanation:

1. Pyrrole:
Pyrrole has a highly delocalized electron cloud due to the presence of a nitrogen atom in the ring. This makes it less reactive towards electrophilic substitution reactions. The lone pair of electrons on the nitrogen atom is involved in the aromaticity of the ring, reducing the electron density on the ring. This decreases the electron density at the ortho and para positions making it difficult for electrophiles to attack at these positions. Hence, pyrrole is the least reactive towards electrophilic substitution reactions.

2. Indole:
Indole has an electron-rich pyrrole ring fused to a benzene ring. The nitrogen atom in the pyrrole ring has a lone pair of electrons that can participate in resonance with the π-electrons of the benzene ring. This increases the electron density on the benzene ring, making it more reactive towards electrophilic substitution reactions than pyrrole. The electron density is highest at the 3-position of the indole ring due to the presence of the nitrogen atom. Hence, indole is more reactive than pyrrole but less reactive than pyridine towards electrophilic substitution reactions.

3. Pyridine:
Pyridine has a nitrogen atom in the ring which is more electronegative than carbon. This makes the carbon atoms in the ring electron-deficient, resulting in a higher electron density at the ortho and para positions. This makes pyridine highly reactive towards electrophilic substitution reactions. The lone pair of electrons on the nitrogen atom is not involved in the aromaticity of the ring, making it available for reaction with electrophiles. Hence, pyridine is the most reactive towards electrophilic substitution reactions among the three compounds.

In conclusion, the reactivity order of pyrrole, indole, and pyridine towards electrophilic substitution reactions is Pyrrole < indole="" />< pyridine.="" />
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Community Answer
With respect to electrophilic aromatic substitution, reactivity order ...
In Electrophilic Aromatic Substitution Reaction (ArSE), More Nucleophilic the Aromatic substrate is, More will be its reactivity towards the ArSE reaction.

Among Pyrrole, Pyridine and Indole- Pyrrole is most Nucleophilic, then is Indole and least is Pyridine.

Reason of this Nucleophilicity can be simply explained by Delocalised electrons Density in these aromatic compounds.
Pyrrole has total of "6πe" delocalised over "5 atoms" of the Pyrrole ring, giving electron density= 6/5=1.2

Indole has total of "10πe" delocalised over "9 atoms" of the Indole ring, giving electron density= 10/9=1.11

Pyridine has total of "6πe" delocalised over "6 atoms" of the Pyridine ring, giving electron density=6/6=1.
Obviously more the delocalised electrons density, more will be its Nucleophilicity.
Clearly, Nucleophilicity order of these aromatic compounds order : Pyrrole>Indole>Pyridine.
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