Chemistry · Alkenes: Geometrical isomerism, mechanism of electrophilic addition, addition of hydrogen, halogens, water, hydrogen halides (Markownikoff's and peroxide effect), Ozonolysis and polymerization

Which of the following alkenes is least reactive towards anionic polymerization?

Which of the following alkenes is least reactive towards anionic polymerization?

  • A. \( H_{2} C=C H C H_{3} \)
  • B. \( H_{2} C=C F_{2} \)
  • C. \( H_{2} C=C H C N \)
  • D. \( H_{2} C=C H C_{6} H_{5} \)

Step-by-step solution

Anionic polymerization proceeds via carbanion intermediates. Electron-withdrawing groups stabilize the carbanion, increasing reactivity, while electron-donating groups destabilize it, decreasing reactivity. Propene (A) has a methyl group, which is weakly electron-donating, making it least reactive. In contrast, difluoroethene (B) has inductive electron-withdrawing fluorines, acrylonitrile (C) has a strong electron-withdrawing cyano group, and styrene (D) has a phenyl group that delocalizes charge via resonance, all increasing reactivity.
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