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COMEDK2024Evening ShiftChemistryAlcohols Phenols and EthersActual

Identify the final product [ D ] formed when Benzyl alcohol undergoes the following series of reactions C ₆ H ₅ CH ₂ OH + SOCl ₂ [ A ]+ KCN [ B ]+ H ₃ O ⁺ (partial hydrolysis) [ C ]+ H ₃ O ⁺ (complete hydrolysis) [ D ]

Options

  1. A4-Chlorobenzoic acid
  2. B2-Phenylethanoic acid
  3. CBenzoic acid
  4. D2-Chlorobenzoic acid

Correct answer

B. 2-Phenylethanoic acid

Step-by-step solution

Benzyl alcohol is C ₆ H ₅ CH ₂ OH . Reaction with SOCl ₂ (Darzens process) converts the alcohol to an alkyl chloride: C ₆ H ₅ CH ₂ OH + SOCl ₂ C ₆ H ₅ CH ₂ Cl + SO ₂ + HCl . Thus, [ A ] is Benzyl chloride ( C ₆ H ₅ CH ₂ Cl ). Reaction of [ A ] with KCN is a nucleophilic substitution ( S_N2 ): C ₆ H ₅ CH ₂ Cl + KCN C ₆ H ₅ CH ₂ CN + KCl . Thus, [ B ] is Benzyl cyanide ( C ₆ H ₅ CH ₂ CN ). Partial hydrolysis of [ B ] with H ₃ O ⁺ yields an amide: C ₆ H ₅ CH ₂ CN + H ₂ O C ₆ H ₅ CH ₂ CONH ₂ . Thus, [ C ] is Phenylacet

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