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JEE Main levelSingle correct optionDifficulty 2 of 3nc270

The aromatic amine shown is diazotised at 0-5 C and the solution is then warmed with water. Which structure is the product?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: A

The compound shown is 3-methylaniline. Diazotisation gives the diazonium salt, which on warming in water is hydrolysed (nucleophilic substitution by water with loss of ) at the same ring carbon. The hydroxyl takes the position of the diazonium group, giving 3-methylphenol (m-cresol).
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