Identify A and predict the type of reaction. [Reactant: 3-bromoanisole (benzene ring with OCH3 and Br meta to each other) with NaNH2 gives A]

Question

Identify A and predict the type of reaction. [Reactant: 3-bromoanisole (benzene ring with OCH3 and Br meta to each other) with NaNH2 gives A] 1. [structure: 2-aminoanisole (OCH3 and NH2 ortho)] and elimination addition reaction 2. [structure: 2-bromoanisole (OCH3 and Br ortho)] and cine substitution reaction 3. [structure: anisole (OCH3 only)] and cine substitution reaction 4. [structure: 3-aminoanisole (OCH3 and NH2 meta)] and substitution reaction

Doubtly AI · Accepted Answer

Answer: 4. [structure: 3-aminoanisole (OCH3 and NH2 meta)] and substitution reaction Key idea: aryl halide with NaNH₂ reacts through a benzyne intermediate, and the product here is 3-aminoanisole. NH₂^- removes the H at C-2 (between OMe and Br), and Br^- leaves. This gives benzyne with the triple bond between C-2 and C-3. NH₂^- adds at C-3, so that the negative charge ends up on C-2, next to the electron-withdrawing OMe carbon (the -I effect stabilises it). Protonation gives 3-aminoanisole, in which NH₂ sits where Br was. The overall result is replacement of Br by NH₂ , the substitution product given in option 4. The 2-amino product is the minor product, and anisole or bromoanisole are not formed.

Identify A and predict the type of reaction. [Reactant: 3-bromoanisole (benzene ring with OCH3 and Br meta to each other) with NaNH2 gives A]

1 answer

Your answer