A Levels Chemistry (9701)•9701/13/M/J/22

Explanation
Benzyne mechanism in aryl halide substitution Steps:
- Compound J (C6H4BrCl) is an ortho-bromochlorobenzene treated with excess hot alcoholic NaOH, a strong base.
- Base abstracts ortho-hydrogen to Br, eliminating HBr to form 3-chlorobenzyne intermediate.
- OH⁻ nucleophile adds to the benzyne triple bond, preferring the position yielding the more stable anion.
- Protonation gives the phenolic product with Cl retained, as Br is the better leaving group.
Why A is correct:
- A shows the skeletal formula of 3-chlorophenol, the major product from regioselective OH⁻ addition to chlorobenzyne per the mechanism.
Why the others are wrong:
- B shows 4-chlorophenol (para substitution, impossible without different isomer).
- C shows 2-chlorophenol (minor product, not major).
- D shows bromochlorobenzene (unchanged starting material).
Final answer: A
Topic: Halogen compounds
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