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When C₆H₅NH₂ reacts with AlCl₃ and CH₃Cl, no reaction occurs. What can be inferred about the directing nature of the (-NH₂, AlCl₃) substituent?

1. The (-NH₂, AlCl₃) substituent directs to the ortho position.
2. The (-NH₂, AlCl₃) substituent directs to the meta position.
3. The (-NH₂, AlCl₃) substituent directs to the para position.
4. None of these statements are correct.

Correct answer: The (-NH₂, AlCl₃) substituent directs to the para position.

Solution

The (-NH2, AlCl3) substituent directs to the para position because the reaction of C6H5NH2 with AlCl3 and CH3Cl results in no reaction, indicating the directing nature of the substituent.

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