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When o-methoxybromobenzene is first reacted with sodamide and then treated with ammonia, which compound is obtained as the final product?

1. o-Methoxyaniline
2. Aniline
3. Methoxybenzene
4. m-Methoxyaniline

Correct answer: m-Methoxyaniline

Solution

NaNH2 abstracts the H ortho to Br (at C6, since C2 bears OMe) generating a benzyne between C1-C6. NH2- adds so the resulting carbanion sits on the carbon next to the electron-withdrawing (-I) OMe; this places the NH2 group meta to OMe, giving m-methoxyaniline.

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