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A Levels Chemistry (9701)•9701/13/O/N/19
Question 20 from 9701/13/O/N/19

Explanation

Electrophilic addition of Br₂ to trichloroethene creates a chiral center

Steps:

  • Trichloroethene structure: Cl₂C=CHCl, an unsymmetrical alkene.
  • Br₂ undergoes electrophilic addition, forming a bromonium ion intermediate on the double bond.
  • Anti addition of Br⁻ attacks the CHCl carbon, yielding Cl₂CBr-CHBrCl.
  • The CHBrCl carbon has four different substituents (H, Br, Cl, CCl₂Br), making it chiral.

Why A is correct:

  • Bromine addition across the C=C bond generates a stereogenic center with four distinct groups, per the definition of chirality in organic molecules.

Why the others are wrong:

  • B. HCl: Markovnikov addition gives CCl₃CH₂Cl, with no chiral carbon (all carbons have identical substituents).
  • C. NaCN: Nucleophilic substitution or addition yields symmetric or achiral products like CCl₃CH₂CN, lacking a stereocenter.
  • D. NaOH: Promotes dehydrohalogenation or hydrolysis to achiral alkenes or alcohols, without forming a chiral center.

Final answer: A

Topic: Halogen compounds

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