1-Chloro-2-methylbenzene (2-chlorotoluene) is treated with KNH2 in liquid NH3. Methyl exerts only a weak electronic effect on the aryne. The aminated products are

2-methylaniline and 3-methylaniline in roughly equal amounts

3-methylaniline and 4-methylaniline

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1-Chloro-2-methylbenzene (2-chlorotoluene) is treated with $KNH X_{2}$ in liquid $NH X_{3}$ . Methyl exerts only a weak electronic effect on the aryne. The aminated products are

A2-methylaniline and 3-methylaniline in roughly equal amounts
B3-methylaniline and 4-methylaniline
C2-methylaniline only
D3-methylaniline only

Answer: A

The only ortho hydrogen is on C-6, so the aryne has its triple bond between C-1 and C-6 and the methyl on C-2. Attack at C-1 (ipso) gives 2-methylaniline and attack at C-6 (cine) gives 3-methylaniline. Because methyl is a weak director, both ends are attacked with similar probability. No 4-methylaniline is possible.

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1-Chloro-2-methylbenzene (2-chlorotoluene) is treated with KNHX2​ in liquid NHX3​. Methyl exerts only a weak electronic effect on the aryne. The aminated products are

Answer: A

More questions on Nucleophilic aromatic substitution and benzyne

1-Chloro-2-methylbenzene (2-chlorotoluene) is treated with $KNH X_{2}$ in liquid $NH X_{3}$ . Methyl exerts only a weak electronic effect on the aryne. The aminated products are