NEET 2017 · ChemistryPrevious Year Question
Identify A and predict the type of reaction: 2-bromoanisole (an aryl bromide bearing an group ortho to ) A
Answer: (A) (A) o-Methoxyaniline ( ortho to ); substitution reaction. With the strong base , the aryl halide reacts via a benzyne (aryne) intermediate.
- A.(A) o-Methoxyaniline ( ortho to ); substitution reaction✓
- B.(B) p-Methoxyaniline ( para to ); elimination-addition reaction
- C.(C) m-Bromoanisole type product; cine substitution reaction
- D.(D) m-Methoxyaniline; cine substitution reaction
Correct Answer
(A) (A) o-Methoxyaniline ( ortho to ); substitution reaction
Solution & Explanation
With the strong base , the aryl halide reacts via a benzyne (aryne) intermediate. The group is ortho to the leaving ; its inductive electron-withdrawal directs the incoming to add to the carbon that originally bore the bromine, giving o-methoxyaniline. Because the nucleophile ends up on the SAME carbon that held the leaving group, the net result is ordinary substitution, not cine substitution.
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