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JEE MainChemistryCarboxylic Acid Derivatives

Two isomers A and B have the molecular formula C ₉ H ₁₁ Cl . Both isomers give an immediate white precipitate when warmed with alcoholic AgNO ₃ , and both yield benzoic acid upon vigorous oxidation with acidic KMnO ₄ . Isomer A is optically active, while isomer B is optically inactive. The structures of isomers A and B respectively are:

Options

  1. AC ₆ H ₅- CH ( Cl ) CH ₂ CH ₃ and p-Cl - C ₆ H ₄- CH ( CH ₃)₂
  2. BC ₆ H ₅- CH ( Cl ) CH ₂ CH ₃ and C ₆ H ₅- C ( Cl )( CH ₃)₂
  3. CC ₆ H ₅- CH ₂ CH ( Cl ) CH ₃ and C ₆ H ₅- C ( Cl )( CH ₃)₂
  4. DC ₆ H ₅- CH ( Cl ) CH ₂ CH ₃ and C ₆ H ₅- CH ₂ CH ₂ CH ₂ Cl

Correct answer

B. C ₆ H ₅- CH ( Cl ) CH ₂ CH ₃ and C ₆ H ₅- C ( Cl )( CH ₃)₂

Step-by-step solution

Oxidation of both isomers A and B with acidic KMnO ₄ yields benzoic acid. This indicates that both isomers contain a single alkyl side chain attached to an unsubstituted benzene ring. Since both isomers give an immediate white precipitate with alcoholic AgNO ₃ , the chlorine atom must be highly reactive, which is characteristic of benzylic or tertiary alkyl halides. The molecular formula is C ₉ H ₁₁ Cl , which means the side chain has 3 carbon atoms. Isomer A is optically active, meaning it has a chiral carbon. The

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