the-electrophilic-aromatic-substitution-reaction-rate-for-indole-is-1013-times-g-1

Question

The electrophilic aromatic substitution reaction rate for indole is 10¹³ times greater than that of benzene. It often reacts under mild reaction conditions. Substitution in indole occurs preferably at position 3.
Explain why indole is more reactive than benzene and why substitution preferably takes place at position 3 than position 2.

Explain why indole is more reactive than benzene and why substitution preferably takes place at position 3 than position 2.

Accepted Answer

Indole is more reactive than benzene because the N atom increases the ring electron density.
The electrophile attack at position 3 is favored because it does not result in the loss of aromaticity of the fused benzene ring.

Answer

Indole is more reactive than benzene because the N atom increases the ring electron density.
The electrophile attack at position 2 is favored because it results in more resonance forms than the attack at position 3.

Answer

Indole is more reactive than benzene because the N atom decreases the ring electron density.
The electrophile attack at position 3 is favored because it does not result in the loss of aromaticity of the fused benzene ring.

Answer

Indole is more reactive than benzene because the N atom decreases the ring electron density.
The electrophile attack at position 2 is favored because it results in more resonance forms than the attack at position 3.

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