A Levels Chemistry (9701)•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
Practice more A Levels Chemistry (9701) questions on mMCQ.me