Isobutylene ( -methylpropene) does not undergo efficient polymerization via free-radical or anionic mechanisms, but polymerizes rapidly to yield polyisobutylene via which mechanism and for what struct

Question

Isobutylene ($2$ -methylpropene) does not undergo efficient polymerization via free-radical or anionic mechanisms, but polymerizes rapidly to yield polyisobutylene via which mechanism and for what structural reason?

Prashant Kotian · Accepted Answer

Correct answer: A. Isobutylene has two electron-releasing () groups, which increase the electron density of the double bond (making it susceptible to electrophilic attack) and heavily stabilize the intermediate tertiary carbocation via hyperconjugation and inductive effects. Thus, it undergoes cationic chain polymerization.

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