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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc055

Assertion (A): Aniline gives a positive carbylamine test, but N-methylaniline does not. Reason (R): Isocyanide formation requires a nitrogen bearing two hydrogen atoms that are removed as two molecules of during reaction with dichlorocarbene.

  1. ABoth A and R are true, and R is the correct explanation of A.
  2. BBoth A and R are true, but R is not the correct explanation of A.
  3. CA is true but R is false.
  4. DA is false but R is true.

Answer: A

In the carbylamine reaction the amine adds to dichlorocarbene, and elimination of two gives . This needs two hydrogens on nitrogen, which only primary amines have. Aniline is primary and N-methylaniline is secondary, so both statements are true and R explains A.
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