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COMEDK2024Evening ShiftChemistryAldehydes and KetonesActual

Identify the final product formed when Toluene undergoes a series of reactions with reagents given in the order: (i) Cl ₂ / Sunlight (ii) H ₂ O / 373 ~K (iii) Acetophenone / OH^- at 293 ~K

Options

  1. Ap-Hydroxyacetophenone
  2. B2, 4-Dichloroacetophenone
  3. C4-Chloro-2-hydroxyacetophenone
  4. D1, 3-Diphenylprop-2-en-1-one

Correct answer

D. 1, 3-Diphenylprop-2-en-1-one

Step-by-step solution

Toluene reacts with Cl ₂ in the presence of sunlight to undergo free radical chlorination at the side chain, yielding benzal chloride, C ₆ H ₅ CHCl ₂ . Hydrolysis of benzal chloride with H ₂ O at 373 ~K replaces the two chlorine atoms with an oxygen atom to form benzaldehyde, C ₆ H ₅ CHO . The reaction of benzaldehyde with acetophenone ( C ₆ H ₅ COCH ₃ ) in the presence of a base ( OH ⁻ ) is a Claisen-Schmidt condensation reaction. This reaction involves the nucleophilic attack of the enolate ion of acetophenone on

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