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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hx275

The compound shown is treated with in liquid ammonia. Select all correct statements.

  1. AA benzyne intermediate is involved.
  2. BTwo isomeric methylanilines are formed.
  3. CPart of the product has the amino group on a carbon other than the one that carried chlorine (cine substitution).
  4. DOnly 2-methylaniline is formed.

Answer: A, B, C

With a very strong base the compound (2-chlorotoluene) loses the hydrogen ortho to Cl (only C-6 has one, since C-2 carries the methyl) and then Cl-, giving a single benzyne. Amide adds at either carbon of the triple bond, giving 2-methylaniline (amine where Cl was) and 3-methylaniline (amine on the neighbouring carbon, cine substitution). So a benzyne is formed, two isomeric products form, and cine substitution occurs; exclusive 2-methylaniline is wrong.
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